Top Vacation Rentals in Beautiful Monterey, MA

Cozy Monterey Home with Porch Walk to Lake Garfield is located in Monterey, just 14 miles from Norman Rockwell Museum and 15 miles from Tanglewood Musical Center. The property is around 15 miles from Tanglewood, 19 miles from Haystack Mountain State Park, and 20 miles from Great Falls. Free Wifi is available throughout the property and Cranwell Spa & Golf Club is 13 miles away. The vacation home features 3 bedrooms, a fully equipped kitchen with a dishwasher and an oven, a washing machine, and 3 bathrooms with a hair dryer. Towels and bed linen are offered in the vacation home. The accommodation has a fireplace. Canaan Village Historic District is 20 miles from Cozy Monterey Home with Porch Walk to Lake Garfield, while Holley Williams House Museum is 27 miles from the property. Bradley International Airport is 40 miles away.

Ocean View • Oceanfront • Internet • Accessibility • Fireplace/Heating • Parking • Sports/Activities • Guest Services • Other • Security/Safety • Child Friendly • View

Relax with the whole family at this peaceful lakeside home. Enjoy the lake-facing deck for dining and drinks. Swim/boat/canoe/kayak/SUPB in Lake Garfield from our dock and enjoy the sun deck. View wildlife: bald eagles soar by, deer wander the woods, and many waterfowl and other birds. Prepare family meals from our fully appointed kitchen or enjoy dozens of nearby restaurants. We are close to Tanglewood, Great Barrington, Lee, Stockbridge & Lenox. Unwind in the Berkshires. We are dog friendly

- "A fabulous getaway. " - "Spent a long holiday weekend at this heavenly lakeside property. Welcoming home with all amenities you will need. Very thoughtful extras are so appreciated. The deck and dock so welcoming-you won’t want to be anywhere else! If you prefer to explore the area great location to do so all within 10-30 minutes. Sandra the host is incredible. Responds quickly and very very accommodating and understanding. We are already planning our return. Run don’t wait to plan yours. "

Hupi House - A Peaceful Wooded Lakeside Retreat offers accommodations in Monterey, 13 miles from Cranwell Spa & Golf Club and 14 miles from Norman Rockwell Museum. This vacation home provides air-conditioned accommodations with a patio. Haystack Mountain State Park is 19 miles from the vacation home and Great Falls is 20 miles away. With free Wifi, this 4-bedroom vacation home features a TV, a washing machine, and a fully equipped kitchen with a dishwasher and oven. Towels and bed linen are available in the vacation home. The accommodation has a fireplace. Guests can relax in the garden at the property. Tanglewood Musical Center is 15 miles from the vacation home, while Tanglewood is 15 miles from the property. Bradley International Airport is 40 miles away.

Child Friendly • View • Parking • Internet • Air Conditioner • Security/Safety • Fireplace/Heating

Air conditioned. Situated on 11 acres, totally private, surrounded by apple orchard, open fields and bordering woods. Newly renovated bathrooms, kitchen, floors.

Built in the 1930s, with beams and siding from a colonial-era barn. Perched on a hillside, with gorgeous views of the distant hills across the valley. Just across the road from Steadman Pond, which is open to tenants, and named for the local craftsman who built the house.

4 bedrooms, 3 baths (2 with marble & glass shower), high-ceiling living/dining room, large fireplace and wood stove, picture windows. Fully equipped kitchen (stainless steel appliances, marble counters). Stocked linen closet, cleaning supplies; washer/dryer. Wi-fi and satellite TV.
Fees vary by month. April $4000 for the month. May $5000, June $6000, July and August $8500 per month. Sept. $5000. October $6000. Nov. $3000. Dec through April (inquire).
Fees are discounted by 10% for rentals of two consecutive months. Apart from rent, fees are charged for cleaning, upgraded plans for internet bandwidth, and above-average use of electricity and propane. These fees typically add to $525 per month, or $17 per day.

Near Lenox (Tanglewood), Great Barrington and Stockbridge. Seven miles south of Lee (Mass Pike exit 2), midway between Tyringham and Monterey. New York is 150 miles, Boston 125 miles. Close by are Tanglewood (Boston Symphony), Jacob's Pillow Dance Festival, Williamstown Theater Festival, many museums, historical sites, fine dining and other cultural spots. See also http://berkshires.org/business_category/what-to-do/

Minimum rental period is one month.

Keywords: Hillside view, on Tyringham/Monterey town line. Colonial-era barn beams and picture windows. Wi-fi & TV. Fully equipped kitchen and linen closet. Air conditioned.

- "From the moment we drove up the driveway and approached this home - we felt like we had entered a different world! A stunning location, breathtaking views, privacy, and a beautiful home. Upon entering the house we found a perfect mix of rustic and modern.Beautifully renovated gourmet kitchen, and bathrooms, welcoming great room with fireplace and cozy wood burning stove, comfortable beds with luxurious linens to sink into.My husband and I spent the first week alone in this heavenly spot and then were joined with kids and cousins filling up all 5 bedrooms. We made some great meals together, went on incredible hikes close by, and all enjoyed nights out at The Lion's Den (underground cellar type tavern at the Stockbridge Red Lion Inn with local musicians) A short drive to Lee for grocery stores, restaurants and anything you need. Can't wait to come back in summer - it's 5 min to swimming and kayaking on Lake Garfield, close to Tanglewood and Jacobs Pillow, and Great Barrington. Owners were helpful, responsive, and in general just great people.This house really works for families - room to all gather together but enough space to find your own spot to relax in!"

14 miles from Cranwell Spa & Golf Club in Monterey, Forget-Me-Not by AvantStay Bold Lakefront Escape provides accommodations with access to a sauna and hot tub. This property offers access to a balcony and free private parking. Tanglewood is 17 miles away and Haystack Mountain State Park is 21 miles from the vacation home. With free Wifi, this vacation home features a TV, a washing machine, and a fully equipped kitchen with a dishwasher and oven. Towels and bed linen are available in the vacation home. The accommodation offers an air conditioning, a heating, and a private bathroom. Norman Rockwell Museum is 15 miles from the vacation home, while Tanglewood Musical Center is 17 miles from the property. Bradley International Airport is 37 miles away.

Fireplace/Heating • Hot Tub • Barbecue/Outdoor Cooking • Wellness Facilities • Parking • Child Friendly • Internet • Sports/Activities • Security/Safety • Air Conditioner

This beautiful gem has been lovingly cared for by our family for almost 20 years—and has served as a relaxing retreat all year round. Our goal: to make you feel like it's your home away from home. It's comfortably furnished and tastefully decorated in the French country style—and is the perfect spot to relax or use as a home base for all your Berkshire activities.

It is family-friendly with child gates for the stairs—and plenty of games, toys, books, and movies for your children. No kids? These things are tucked away so you don't need to use them if you don't want!

There are 2 bedrooms upstairs: one master with a king-size bed and one smaller bedroom with a twin bed and pull-out twin bed. There is one downstairs bathroom. An open downstairs floor plan flows from the living room (with a wood-burning stove fired up by plenty of wood we have stored for you), to the kitchen to the dining room.

There's a super comfy pull-out sofa with a queen-size bed in the living room if you need extra space for your family or friends.

Off the dining room is the beautiful screened-in porch where you can sit for hours relaxing and enjoying the breeze and sounds of the Loom Brook from the back of the house. A connected deck allows for easy grilling with the gas grill.

In the summer, our house is just minutes from Lake Garfield, where there's a lake beach perfect for kids and adults alike! A lifeguard is present during the summer months—making it perfect for swimming out to the floating docks (it will bring back camp memories!). You can also canoe and kayak on this lake. We have sand toys, beach umbrellas, and chairs ready for your use. Love to hike? The Appalachian Trail crosses our road, which is perfect for walking any time of the year. We're also situated right near the Beartown State Forest with all its trails. Love to mountain bike? We have one bike available for your use; feel free to bring up your own bikes and ride along our dirt road — or on the nearby trails.

We're also close (about 20 minutes) to blueberry picking and apple picking.

We're 40 minutes from Tanglewood, 45 minutes from Jacob's Pillow, and just 25 minutes from the town of Great Barrington with its restaurants, bars, Triplex cinema, and the historic Mahaiwe Performing Arts Center.

Fall brings the beautiful splendor of the fall foliage home here; it surrounds the house and everywhere you turn. Go for walks, take in kayaking or canoeing on Lake Garfield, or just take a visit to the nearby Taft Farms for their pumpkins, fresh cider and hot donuts, and corn mazes.

Our home is just 15 minutes from Butternut Ski Resort, which is where our children have learned to ski from age 3. It's the perfect family resort and our home is close enough to put season's passes (or just one-day passes) to good use. You'll love coming home to the warmth of the wood stove and the comfort of our home. We also have snow shoes available for your use.

We are minutes from the town of Monterey, which is small but quaint. We are also just minutes from the Roadside Cafe, the perfect country diner for breakfast, lunch, and dinner Wednesday through Saturday. (There's also Great Barrington, Stockbridge, Lee, and Lenox—as well as Pittsfield...which is 45 minutes away...for more delicious restaurants.)

We are about a 25-minute drive from the outlets in Lee, about 30 minutes to Stockbridge (with the quaint and historic Red Lion Inn) and Lenox with Miraval Resort and Wyndhurst Manor & Club (where you can play golf), the Kripalu Yoga Center, and Tanglewood (as well as Canyon Ranch).

Pets are allowed by individual request.

Upgraded Internet (2020), with two satellite dishes, allows for more Internet surfing, Zoom calls, and at-home work. An additional DISH satellite offers more than 100 channels on the TV.

Our goal: to have you fall in love with our home just as much as we love it. We want you to feel this is your Monterey home away from home!

- "Perfect spot to relax" - "It was wonderful. So peaceful and quiet, yet very comfortable with all the amenities you want or need. Definitely a go to when I visit the Berkshires again." - "What a lovely property. Staying at a rental was pushing my BFF’s comfort zone, but I convinced her to give it a try. Because of this lovely rental and overall experience, she is now hooked. The covered porch is the perfect place to enjoy a cup of coffee, listen to the rain on the roof and take in the woods all around. I would love to stay there again when in the area."

14 miles from Norman Rockwell Museum in Monterey, Monterey Home with Hot Tub, Pool and Game Room! provides accommodations with access to a hot tub. Guests can go for a swim in the private pool. Free Wifi is available throughout the property and Cranwell Spa & Golf Club is 13 miles away. The air-conditioned vacation home consists of 6 bedrooms, 3 living rooms, a fully equipped kitchen with a dishwasher and a coffee machine, and 6 bathrooms with a hot tub and a hair dryer. Towels and bed linen are provided in the vacation home. The accommodation has a fireplace. Tanglewood Musical Center is 15 miles from the vacation home, while Tanglewood is 15 miles away. Bradley International Airport is 41 miles from the property.

Fireplace/Heating • Security/Safety • Guest Services • Wellness Facilities • Parking • Sports/Activities • Accessibility • Other • Pool • Hot Tub • Internet • Child Friendly

The lakeside house is built on a 1.1 acre lot with view of Lake Garfield. It is only a few minutes walk to the town's beach with life guards on site. This one-level modern home has vaulted ceilings throughout. There are two master suites with king beds and two other bedrooms with queen beds. A walk out deck from one of the master bedrooms so you can enjoy morning coffee. Three common spaces include a loft for guests to chill out. A new washer and dryer is in one of the guest bathrooms. The kitchen with new stainless steel appliances is equipped with premium cooking tools and pots. Guests can hang out at the kitchen counter bar stools while someone is preparing meals. A gas grill is available on the front deck which can be accessed from the kitchen or the great room. There are two gas fireplaces to keep you cozy at night time.

In the summer, Jacob’s Pillow Dance Center and Tanglewood Music Center are about 25 to 30 minutes away. In the winter, Ski Butternut resort is about 10 minute drive. Monterey is a small secluded town with one general store, the Bidwell Museum and a few small farms where you can get fresh milk, eggs, pork, chicken, maple syrup, goat cheese, fruits and vegetables. It is only a 15 minute drive to Great Barrington where local gift shops, organic grocery stores and farm-to-table and gastronomic restaurants are located. If you like shopping, Lee Premium Outlets is 15 minutes away.

- "Well appointed home for a family vacation. Nice lake for swimming and kayaking. Plenty of nearby attractions for all ages!" - "My siblings and I gathered with our significant others in this well equipped and comfortable house nested in the woods in the Berkshires. We enjoyed sharing memories in this quiet setting. The beds were so comfortable, we all slept well. We were sorry we couldn’t see the lake from the deck because of trees and foliage but we were able to walk to the beach. We didn’t use the kayaks as they were too heavy for the group (all over 75). We enjoyed our trips to Jacobs Pillow and the Norman Rockwell museum. We spent our evenings gathered around the house’s large dining table eating our evening meal while laughing about our youth."

Monterey Haven Less Than half Mi to Lake Garfield with Kayaks offers accommodations in Monterey, 18 miles from Tanglewood Musical Center and 18 miles from Tanglewood. The air-conditioned accommodation is 17 miles from Norman Rockwell Museum. Free Wifi is available throughout the property and Cranwell Spa & Golf Club is 16 miles away. The vacation home features 3 bedrooms, a fully equipped kitchen with a dishwasher and an oven, a washing machine, and 1 bathroom with free toiletries. Towels and bed linen are offered in the vacation home. The property has an outdoor dining area. Haystack Mountain State Park is 21 miles from Monterey Haven Less Than half Mi to Lake Garfield with Kayaks, while Great Falls is 22 miles from the property. Bradley International Airport is 37 miles away.

Internet • Security/Safety • Other • Parking • Guest Services • Accessibility • Child Friendly

Sweet, newly renovated cottage, in a blissfully tranquil setting on Lake Garfield in Monterey, MA. Secluded, private, yet close to amenities, the cottage sits on a secluded 9 acre wooded lot along with one other house. 100yd walk to the private dock (shared with the other house). Monterey is at a higher elevation in the Berkshires (above Great Barrington), so the air is cool and refreshing during most of the summer. The cottage has been completely renovated and is equipped with WiFi and air conditioning. New, open-plan kitchen has full range of appliances, including dishwasher. Full-size front loading washer and dryer. Living room contains a plush L-shaped sofa, flat-screen TV/DVD player with Direct TV package, wood burning stove, and lounge chairs. Indoor and outdoor dining areas. Workspace with desk and bookcase. The master bedroom has a queen bed with high quality gel mattress, antique dresser and antique wardrobe. The spare bedroom has a queen on bottom/full on top/combination bunk bed, also fitted with high quality gel mattresses. Large porch with dining and lounging seating. Overhead fan and baseboard heat. Linens, blankets, pillows and towels provided. Outdoor lounge chairs, fire pit, propane BBQ grill, and x-large 2-person hammock. One Canoe and two kayaks.

A 15 minute walk from the cottage is the village of Monterey, MA. Dotted with pre-colonial buildings, it is a hidden jewel in the Berkshires. Within walking distance there is an honesty farm stand where you can get the freshest veggies, as well as a farm that produces goat cheese from their own herd. Monterey is home to the historic Bidwell Museum. Monterey is a 20 minute drive from Great Barrington, where you can find a large variety of restaurants, grocery stores, theaters and shops. In addition, all the attractions of Great Barrington and the Berkshires are at your fingertips: Tanglewood, Kripalu Yoga Center, Norman Rockwell Museum, Hancock Shaker Museum, the Clark Museum, the WE DuBois Museum and the Naumkeag Museum.
Natural beauty abounds. The Appalachian Trail is nearby for hikers, and beautiful back-country roads are here for bikers. Your neighbors will include owls, eagles, herons, ducks, and possibly a curious baby bear (please don’t leave food outside!). A perfect, soothing get-away.

Cottage Features

- Approximately 1,275 sq ft. Sleeps up to 5
- 1 queen bed in master bedroom. 1 queen bed/1 full bed (bunk) in second bedroom.
- Extremely comfortable gel mattresses
- Covered porch with sitting and eating areas
- Indoor and outdoor dining areas
- Propane BBQ grill with accessories
- Air conditioning
- Wood-burning stove
- X-large 2 person Hammock
- Outdoor lounge chairs with fire pit
- Fully equipped kitchen with new appliances. Full size range and refrigerator. Microwave and dishwasher. Toaster oven, basket type #2 and individual pod coffee makers, electric water kettle, blender. High quality pots and cooking utensils
- Full size front-loading washer and dryer
- TV with DVD and Direct TV package
- 900MHz speed Internet
- Fans
- Linens, bath towels and beach towels provided
- Hair dryer
- Landline phone
- Private dock (share with main house)
- Dogs under 20 pounds allowed. $150 cleaning fee

A note concerning cellphone reception. We are in a natural area, so cellphone reception may be limited to texting. Alternatively you can use WhatsApp or the landline for local voice calls.

- "I loved it. Quiet, in the woods at the end of a dead end gravel road - no traffic. Lovely farmers porch to read and enjoy the wildlife and view. Fire pit in front yard. Property manager and owner very responsive. I was there in late fall so didn't use the kayaks and canoes available down by the lake. Met friendly neighbors on my walks. I definitely plan to return." - "Very private, woodland sanctuary filled with birdsong. A lovely covered porch with comfortable chairs provided a great place to have morning coffee, read a book and watch the birds zooming among the trees. The cottage is well equipped and comfortable."

Stunning log cabin in the Berkshires on 10 private wooded acres complete with brand new 4 season hot tub, in-ground pool with electric cover, gorgeous pickleball and basketball court, stunning fire pit perfect for s'mores, relaxing hammock, stocked veggie garden, private outdoor shower, new built in grill, tons of indoor and outdoor games, beautiful screened in porch, stocked gourmet kitchen, radiant heated floors, huge family room with fireplace, finished basement with billiards, darts and big screen TV. 3 gorgeous bedrooms, 3 big bathrooms with beautiful tile work and heated floors, and even 2 extra twin beds downstairs. This is a great getaway from the hustle/bustle. Right near the lake, skiing, town of Great Barrington with great stores and restaurants, Tanglewood, Stockbridge, Lenox, Butternut, theaters, and more. Relax and enjoy! It's all new, furnished and has everything you need for a perfect getaway with just family or with friends from afar.

- "It is much more than a cabin! It is that Berkshires cabin feel you want, but not rustic or creaky. Beautiful back yard, all the amenities you could want, spacious bedrooms. The basement was an unexpected bonus. A great place and great location!" - "Our group of five old friends had a wonderful time at "the Cabin" which is really an amazing log house. It had so many great features-- hot tub, pool table, lovely outdoor shower and sitting area -- but the screened porch was our favorite! Cozy and airy, even during downpours. We hope to return in the future. Thank you Jim and Lisa."

RENOVATED Charm: 1920's cottage with 3 acres of natural surroundings. A short, 5 minute walk via nature trail and stairs to dock on Lake Garfield with Adirondack chairs, 2 kayaks and a large canoe. 5 bedrooms and 2 bathrooms provides plenty of space for your family enjoyment. At home enjoy the large, bright family room equipped with a flat screen TV with Satellite service, high speed internet & DVD player. In addition, there is a large living room and dining room area with a charming old stone fireplace.

The screened in porch is another great spot to relax...featuring a table for 6 and a seating area to enjoy the (winter) views of the lake, yard & perennial garden. The kitchen has a large eating island area brightly lit with skylights and stool seating for 5. The kitchen is equipped for every cooks needs...and plenty of cutlery & plates to feed a crowd! The large master bedroom is downstairs with four additional bedrooms upstairs.

It's Always quiet and serene on Lake Garfield. The lake is over 300 acres but seems uninhabited! Everyone has loved our house...and our great town. We hope you will enjoy it as well!

- "We absolutely loved our time in Monterey. The home is spacious and beautiful. It had everything we needed to enjoy our stay." - "Very comfortable house for all of us. We enjoyed the wood stove which really heats up. the kitchen is well equipped, has everything we needed; Very convenient to Great Barrington; the owner was very easy to work with. Hope to return again!" - "Lovely stay. The lakeside is beautiful and so relaxing. Beds are very comfortable and there was plenty of room for all of us."

This secluded and private one-bedroom cottage has two gas stoves to keep you toasty in winter and A/C to keep you cool in summer as you enjoy the country views out of every window. Comfortably appointed and super clean, the cottage features an enclosed porch, a large outdoor deck, a cozy living/dining/kitchen area, and a fenced-in backyard, making it ideal for dog owners. The deck has lounge chairs, a gas grill, a dining table with an umbrella, and a fire table. You are centrally located to great hiking, lakes, skiing, and charming towns. The lovely town beach on Lake Garfield is a 3-minute drive away. And folks tell us the bed has the most comfortable queen mattress! Across the road, there is, in fact, a beaver lodge! Three-night minimum for holiday weekends.

- "New, very clean and well equipped unit. Nice country setting. Recommended." - "A very comfortable and cozy place to unwind. Great hosts!" - "Perfect for a couple" - "Just returned from our stay at The Beaver Lodge. Very clean and comfortable with easy check in and out. Communication with owner was easy and helpful. We would definitely recommend." - "Joel's house in Monterey was just perfect for our New Year's getaway! It was comfortable, clean and well stocked. Joel was also an amazing host. Check in and check out couldn't have been easier. Also Joel went above and beyond for me. I left two sweaters at the house and Joel was kind enough to retrieve them and send them back to me. Thank you Joel!"

Curl up with a good book by the fire and gaze out at the dreamy picturesque mountain and lake views..... Or ski, swim, hike and enjoy so much more that the Berkshires has to offer in this centrally located Southern Berkshire county home.

Private mountain top adventure awaits..

Centrally located in Southern Berkshire County: 10 minutes from Butternut ski, 15 minutes to Great Barrington, 20 minutes Stockbridge & Lenox and 2 ½ hours from NYC and Boston.

Great Room: Spacious open floor plan great for entertaining friends and family. Living room is furnished with 2 comfortable deep seated sofas, accent chair and 2 ottomans and 2 large coffee table’s, Relax and enjoy collection of movies on dvd players, listen to music on the stereo system or play games (we have a variety of board and card games).

Family room (downstairs) with large sectional and daybed for extra sleeping. There is a TV and dvd player.

Chef’s Kitchen: Stainless steel appliances, large island that seats 6 and dining table that seats six...

4 Bedrooms: 1 King size, 3 queen size all with luxury mattresses and bedding.

2 Bathrooms: Master bathroom (upstairs) features with shower and deep soaking tub.
*we are building an additional 3rd bathroom off the hallway, but for now the bathroom upstairs is in the master bedroom that is shared with the guest bedroom.

Screened sunroom nestled amongst the woods with beautiful views of the lake… Provides a comfortable setting to relax and includes a sectional sofa, chair & ottoman and table with 4 chairs to enjoy the outdoors.
Hammock’s, fire pit, hot tub and grill set up weather permitting…

NOTE:
Driveway: The house is located on the top of a long private gravel road, it gets snow plowed when the snow reaches 4” but it’s best to have a car that suitable in the snow.

We have updated home to include Central Heat & Air Conditioning Fall 2019.

Internet: Wifi throughout the home.

Movies & Cable TV:
2 Large Flat Screen TV’s equipped with Smart TV's and DVD players including premium’s like Netflix, HBO, SHOWTIME and STARS.

Stereo system with speakers is set up in the great room with record player and aux cord to hook your phone to play any music on your phone library.

Phone:
There is also no house phone some cell phone providers work better than others.

We will be providing all our guests with our How to's, House Rules and an inventory list that each guest must read and email back with confirmation that they have read and understand.

* ID verification required before booking.

- "Large, clean, fully equipped, tasteful modern decor with spectacular view of lake and mountain. Family enjoyed relaxation, playing bocce and corn hole and hiking on numerous trails in the area" - "We enjoyed great family dinners at the beautiful home!" - "The house is beautiful and very well equipped, the view breathtaking! Johanna is very pleasant to talk to and very responsive, she also provides a very helpful guide with instructions and recommendations. I would definitely recommend!"

Family vacation lake house on lake Garfield, Monterey MA. Beautiful lake location nestled in the hills of the Berkshires on a private road tucked amongst old growth hemlocks. With great views up and down the lake from either of two large platform docks, or the front deck of the house or large sun deck will grill and eating area. This lake home is a great escape it featuring 2 kayaks (single and double), 2 SUPs, a row boat and many floats for relaxing in the water. The swimming and fishing is very good as the water is clean with cool spots in this spring feed lake. Centrally located to access all the Berkshire' has to offer, whether concert going at Tanglewood or shopping and dining in Great Barrington, or Stockbridge, Lenox, Pittsfield or hiking, bird watching, exploring or just relaxing and take in a clearer view of the night sky this could be the best balance you are looking for.
Our home is also a nice balance between the look and feel of an all wood cedar and pine lake cabin, but large enough to sleep 10 or more with modern kitchen, large family dinner table. Lots of space with 6 split levels tiered down toward the shore line. 5 bed rooms ranging from a bunk room down stairs to a private suite up top, 4 queens, 4 twins. GUESTS PROVIDE OWN LINENS AND TOWELS. Extra blankets and pillows in each bedroom.

- "Enjoyed our stay down by the lake! Easy to get to, everything was well described and thought out and Steven was easy to reach and prompt with any response. Great week." - "What a perfect setting!! The owner is lovely to work with. The home is charming and spacious and just perfect for a group to gather..and it comes with a touching history too!" - "Had a great time again this year. Perfect location, lovely lake, great host." - "House has a great balcony to enjoy the view of the lake and has great privacy, yet close enough to groceries, shopping, and good restaurants, (15 minutes away). Our family loved paddle boarding and using the row boat. The two docks provided easy access and views of the lake. Our family of eight totally enjoyed our peaceful week."

Get away from it all at our beautiful Berkshire lakefront wooded retreat. Swim, canoe, kayak, paddleboard, sunbathe, hike, bike, explore during the day. In the evening perhaps take a short drive to Tanglewood, Jacobs Pillow, Shakespeare & Co, or Mahaiwe Performing Arts, or to the movies in Great Barrington. Have dinner at the Red Lion Inn, or one of the fabulous restaurants nearby, or have it at home as you watch the sunset over the lake.

This private, modernized (major renovation completed 2018-19), 5 bedroom* cottage consists of two floors. The upper floor has a fully equipped kitchen , a large great room with a dining and living area, featuring a beamed cathedral ceiling, skylights, a dramatic fireplace, and an entertainment area with a wide screen TV. The dining room table seats eight and overlooks the lake. A transitional kitchen "island" seats an additional four. A screened porch overlooking the lake extends off of the dining area. An open porch overlooking the lake extends off the living room area. The master bedroom, with a king bed, and one full custom bath are on this floor. Downstairs, three bedrooms (two with queen beds one with one twin bed) have lake views. The fourth bedroom has two twin beds. A full bathroom, a second refrigerator, and a utility room with a washer and dryer are on this floor. The middle bedroom has large sliding glass doors which open to a large patio area with a garden, lawn chairs, fire pit, and two picnic tables. A four burner Napoleon gas grill overlooks the patio, with easy access to the kitchen. The downstairs does not have AC, but the upstairs living room and master bedroom has AC. The downstairs generally stays cool as it is nestled in the hill.

A flight of half-steps (constructed for a gentleman who had just had a knee replacement) leads to the dock and the lake. Two canoes, two kayaks, and two stand up paddleboards come with this rental. There are also various floats for swimming. Lake Garfield is managed for weed control (the water is lowered each winter to kill off the weeds) so the water is one of the the clearest in Massachusetts.

A magical lakeside retreat with all the comforts of home and easily accessible to the world-renowned art, culture, dining, and entertainment of the Berkshire hills. Look forward to a memorable vacation.

Keywords: Berkshires, Western Massachusetts, Lakefront, Waterfront, Lake, Lake Garfield, Tanglewood, Jacobs Pillow, Monterey, Great Barrington, Lenox, Stockbridge, summer rental, vacation home, retreat, swimming, boating, rustic, wooded, Cottage, House, chalet

- "This is our second time renting this beautiful, Berkshires, lakeside home.The attention to details for entertainment and relaxing inside and out is superb. Lake Garfield is pn the property. It is very clean, refreshing , not too populated and so accessible for swimming and all types of floating snd boating." - "On Lake Garfield we learned the 1 1/2 yr old loves boats. He sat calm and content in the canoe and the sit-upon kayak, even in a tight life-jacket. His 2-yr-old cousin, not so much. Swimming was her jam. Every family member found something to love about the house. The cozy bedrooms, the garden patio, the game closet, the well-equipped kitchen. The house had comfortable spots for conversations heavy or light. The location near Great Barrington is convenient, and hikers can easily get to the AT on Main Road. Highly recommended."

Supremely relaxing modern home in wooded setting with screened in outdoor porch as well as a firepit, patio and gas grill. Close to public town beach. Close to Butternut, Catamount, Jimney peak as well as excellent hiking and biking. Great Barrington, Tanglewood, Jacobs pillow, great restaurants and markets close by.

- "My 7.5 year old son and I stayed at this house for close to three weeks and it was exactly what we were looking for. My family and I have been coming to the Berkshires for over five years in both the winter and summer and have been on the eternal rental search mostly due to space and cleanliness. Our search is finally over. The house is very spacious, clean, and easy to access. The screened in porch is fantastic and the kitchen had everything we needed. I was able to exercise in the basement and do work as well. Any question I had Howard was easily reachable and accomodating. The house is two minutes from Lake Garfield which we went to many times with our dinner after my sons day at camp. Only things to know and they are beyond minor—if you are not familiar w the Berkshires Monterey is a teeny bit further so easy to Great Barrington but adds some time getting to Lenox, Pittsfield and beyond. The smaller room where my son chose to stay is the only one without air so it did get hot in there. Would recommend having a fan accessible. In my case he could have easily changed rooms he just chose not to so that is on us. And finally for the two of us the TV set up was fine but for a family of four or more its a little awkward but definitely doable and two of the bedrooms also have a tv. I will definitely be bringing the rest of my family back in the winter and I know the four of us will have a great time hunkering down, cooking, and hanging out."

Please enjoy our little slice of paradise! Perched just up the hill from Lake Garfield, The Hupi House offers a truly magical view of the lake and mountains for miles beyond. Let breathtaking sunsets be your evening entertainment! Inside you will find a stocked kitchen, high-quality appliances and bedding, fast wifi, and wooded seclusion. Outside you will find swimming, kayaking, hiking, leaf-peeping, star-gazing, skiing...Minutes to Ski Butternut, Great Barrington, Jacob s Pillow, Tanglewood.

The Space

Our place is a beautiful rustic house in the woods with quiet privacy, the modern amenities you need to feel at home, and a view you will talk about after your visit ends. Easy access to Lake Garfield (lake access included), 10 Minutes from Ski Butternut, 15 minutes from Great Barrington.

The main first floor living area is a lovely open space with galley kitchen, woodstove, ample seating for dining and relaxing. Sliding doors lead to the deck with lounge chairs and grill. Two bedrooms and a bathroom with tub round out the main level.

Upstairs you have a master suite: a lovely tucked away loft with proper closing door, king bed, tv, and en suite bath with shower.

Downstairs is a finished lower level with two twin beds, a queen sleeper sofa, den area w tv/video games, piano, laundry area, and doors that open to the outside under the deck. This is a flexible area, perfect for kids, well-appointed for adults.

Guest Access

Our house is a conveniently situated location from which to visit countless Berkshires attractions, including Tanglewood, Jacob s Pillow, Norman Rockwell Museum, W.E.B. Dubois National Historic Site, The Bidwell House Museum, Animagic Museum of Animation, Bard College at Simon s Rock, Berkshire Theater Festival, Berkshire Int l Film Festival, hiking at Umpachene Falls and Beartown State Forest, and a bit over an hour drive from MassMOCA. The charming towns of Great Barrington, Lenox and Stockbridge are all 15-20 minutes away. Lake Garfield Beach is a 20-minute walk or 4-minute drive down the hill. Ski Butternut, a hub for Northeast skiers, is a 10-minute drive, and a major attraction for winter travelers.

Interaction with Guests

The house is yours and you will not be disturbed by us. Should you need anything we are always available over phone/text/email, and we have reliable local help, should problems arise.

Other things to note:

--The kitchen/main living space is only accessed by stairs, so keep that in mind for those with additional accessibility needs.

--The driveway is quite twisty! We recommend, minimally, a front wheel drive vehicle for winter stays.

--Parents with small children should be advised that any playing on the deck or at the foot of the deck/front side of the house must be monitored for safety, as there are spaces for a wee one to sneak thru the deck railing, and as there is a steep drop off into woods in front of the house.

—We aim to allow people to feel as comfortable here as possible, always are trying to improve guests’ experiences, and are almost always reachable and quickly responsive to any issues that arise. While we are here to help, guests should know it is not a hotel, but a lovely, rustic house in the woods. There are quirks; our patio door leaves a small crack which does not create any noticeable draft but does not seal tight. Some light switches were installed in strange places. We are as diligent as possible in the battle vs critters, as the woods is their home too, but there will occasionally be signs of a country mouse. It is on the side of a small mountain and there are storms that take the power out a few times a year. Workers can be hard to get here quickly. This is just life up here in the Berkshires, and we want guests to come with appropriate expectations so everyone is happy.

- "Fantastic home to unwind and enjoy the beauty of true peace and quiet." - "The space was great for our family and gave us a nice relaxing trip away from the city." - "I stayed three nights at Greg & Meg’s Monterey cabin with best friends of 30+ years and we had a wonderful time. The home is well-appointed and comfortable, with beautiful lake and mountain views. Our hosts were communicative but gave us space. It rained the entire four days, but we were cozy with the wood stove and enjoyed a movie night in the downstairs space the last night. Not a ton to do in the area but that’s what we wanted — a wine tasting and a brewery, a restaurant meal here and there, and the Norman Rockwell museum was more interesting than I’d expected. It was just enough, really - totally relaxed weekend. We even had a movie star sighting while eating brunch at the Southfield Store (delicious French toast btw!). Already looking forward to our next visit. Thank you!"

Discover historic attractions and unbeatable outdoor recreation at this Monterey vacation rental featuring a stone patio, gas grill, screened porch, and more! This 3-bedroom, 2.5-bath Lake Garfield home has modern amenities with an antique charm. Take the kayaks on the lake, venture out to the Butternut Ski Area to shred snow, or visit famous places like the Norman Rockwell Museum or Tanglewood. Then, return home to cozy up by the wood-burning fireplace and enjoy a game night with the family!

-- THE PROPERTY --

MassTaxConnect ID #: C0055491930 | Kayaks Provided | Smart TVs

Bedroom 1: Queen Bed | Bedroom 2: 2 Twin Beds, 1 Twin Trundle | Bedroom 3: Queen Bed

OUTDOOR LIVING: Lake access, walk to beaches, patio/balcony, beach chairs + towels, boating, gas grill, private yard, screened porch, hiking trail access on-site, basketball court
INDOOR LIVING: Smart TV w/ cable, en-suite bathroom, fireplace, stereo, DVD player, board games, books, iPod dock/MP3, bathtub/shower
KITCHEN: Refrigerator, microwave, stove/oven, dishwasher, coffee maker, toaster, spices, cooking basics, dishware/flatware
GENERAL: Central heating, ceiling fans, complimentary toiletries, washer/dryer, linens/towels, hair dryer, hangers, iron/board, landline phone, trash bags/paper towels
FAQ: Steps required for access, limited cell service, 1 external security camera (facing out), no A/C
PARKING: Driveway (3 vehicles)

-- THE LOCATION --

OUTDOOR ADVENTURES: Lake Garfield Beach (0.3 miles), Diane's Trail Trailhead (3 miles), Bob's Way (4 miles), Berkshire Trout Hatchery (4 miles), Otis State Forest (7 miles), Tolland State Forest (15 miles)
SKI RESORTS: Butternut Ski Area and Tubing Center (7 miles), Otis Ridge Ski Resort (8 miles), Ski Blandford (18 miles), Bousquet Ski Area (18 miles), Catamount Mountain Resort (18 miles), Ski Sundown (32 miles)
AREA ATTRACTIONS: Bidwell House Museum (2 miles), Ashintully Gardens (4 miles), Norman Rockwell Museum (13 miles), Shakespeare & Company (14 miles), Chesterwood Studio (14 miles), Tanglewood (15 miles)
AIRPORT: Bradley International Airport (42 miles)

-- REST EASY WITH US --

Evolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.

-- POLICIES --

- No smoking
- No pets allowed
- No events, parties, or large gatherings
- Additional fees and taxes may apply
- Photo ID may be required upon check-in
- NOTE: Steps are required for access to this property
- NOTE: This property does not offer air conditioning
- NOTE: The property does have cell phone service, but it may be spotty since the property is located in a rural area. Please check with your provider to confirm your service quality
- NOTE: Your safety matters. This property features 1 exterior security camera located on the house exterior facing the driveway. The camera is outward facing and does not look into interior spaces. The camera does not actively record video or sound while guests are in residence

- "Artistic, warm and spacious - one of a kind. We really enjoyed our stay, thanks to Amy (the owners) check in and check out was not a problem. Will be happy to come back next time In Berkshires" - "This property is perfect. Been vacationing in the Berkshires twice a year for the past ten years and have rented multiple homes. This one is at the top of our list. Clean, roomy, and had everything we needed. I'd highly recommend it." - "We loved the atmosphere of this place, clearly feeling the deep sense of home that comes through via the art work, the music, the pictures and stories of family members. The screened porch was lovely for meals."

Gather up your friends and family for the ultimate group getaway at this Monterey vacation rental! The home has nearly 4,500 square feet of interior space — including a game room, a huge sunroom, 6 bedrooms, 4 full baths, and 2 half baths — and plenty of outdoor space for everyone to enjoy. Plus, you’ll have easy access to endless outdoor adventures. Hit the slopes at Butternut Ski Area or Otis Ridge — both less than 10 miles away — take a hike on the local trails, or catch a show at Tanglewood!

-- THE PROPERTY --

MassTaxConnect ID C0463041930 | Deck w/ Gas Grill | Furnished Sunroom | 8 Mi to Butternut Ski Area | 15 Mi to Tanglewood

Bedroom 1: King Bed | Bedroom 2: Queen Bed | Bedroom 3: Queen Bed | Bedroom 4: Queen Bed | Bedroom 5: Queen Bed | Bedroom 6: Queen Bed | Office: Queen Sleeper Sofa | Basement Bonus Room: Queen Bed, 2 Twin Sleeper Chairs | Additional Sleeping: Full Air Mattress

INDOOR LIVING: 3 Smart TVs, fireplace (wood provided), ping-pong/pool table, arcade machine, foosball table, board games, home office
OUTDOOR LIVING: Pool (depth 4’-9’), hot tub, large backyard, playset, basketball hoop, pickleball net
KITCHEN: Dishwasher, 6-burner gas stovetop, oven, refrigerator, microwave, cooking basics, dishware & flatware, Keurig K-Duo, percolator, coffee provided, toaster oven, beverage fridge, trash bags & paper towels
GENERAL: Free WiFi, central A/C & heating, complimentary toiletries, linens & towels, in-home laundry, laundry detergent, hangers, hair dryer, keyless entry
FAQ: 3 exterior security cameras (facing out)
ACCESSIBILITY: 4 steps for entry, 3-story home, bedroom & full bathroom on 1st floor
PARKING: Garage (2 vehicles), driveway (4 vehicles)

-- THE LOCATION --

SKI RESORTS: Butternut Ski Area and Tubing Center (8 miles), Otis Ridge (9 miles), Bousquet Mountain Ski Area (19 miles), Catamount Mountain Resort (19 miles), Ski Sundown (33 miles)
OUTDOOR ADVENTURES: Lake Garfield Beach (2 miles), Diane's Trail Trailhead (3 miles), Otis State Forest (8 miles), Tolland State Forest (16 miles)
EXPLORE THE AREA: Berkshire Botanical Garden (13 miles), Tanglewood (15 miles), Berkshire Museum (20 miles)
AIRPORTS: Bradley International Airport (43 miles), Albany International Airport (62 miles)

-- REST EASY WITH US --

Evolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you.

-- POLICIES --

- No smoking
- No pets allowed
- No events, parties, or large gatherings
- Additional fees and taxes may apply
- Photo ID may be required upon check-in
- NOTE: This 3-story home requires 4 steps for entry. While there is a bedroom and a full bathroom on the 1st floor, additional stairs are required to access bedrooms on the 2nd floor and in the basement
- NOTE: Your safety matters. This property features 3 exterior security cameras: camera 1 is on the front patio facing the driveway, camera 2 is above the garage facing the driveway, and camera 3 is on the back of the house facing the yard/pool. The cameras are outward facing and do not look into interior spaces. The cameras actively record video and sound

- "Beautiful property. Lovely grounds. Clean and so much fun for the little ones. Communication and service were excellent. " - "Loved the common area. Perfect for the group to cook, gather and eat. " - "Wow what a property—we had a wonderful group with ages spanning 5 years-75 years old. This property has enough space and amenities to keep everyone happy! The local hosts were easy to connect with, and the house is stocked with everything we needed to have a great time. We loved all of the premium touches—this was an easy “home away from home” and we would love to come back when the pool is ready to swim in! "

★ Recognized as one of our best. This home was a finalist in the 2025 AvantStay Awards, our annual celebration of top-tier stays.

Bold, modern design perched right above the shores of Lake Garfield. Forget-Me-Not is a vast, three-story Berkshires retreat with unobstructed lake views, a lofted, industrial-chic design, and plenty of ways to keep your group comfortable and entertained. The home's moody exterior gives way to a bright, open common area where you'll find huge windows for tons of natural light, a spacious kitchen, and vaulted ceilings over the main living room. A cozy sunroom leads to Forget-Me-Not’s large deck, which features a BBQ grill and outdoor dining table for al fresco meals overlooking the water. Soak in the hot tub, or head inside for a round of ping pong, cornhole, or heat up in the custom-built sauna. The lower floor features a second living room complete with a kitchenette and pool table, so your group will have plenty of room to spread out. With tons of privacy and unbeatable proximity to the shoreline, this contemporary lake retreat is ready to show you the best of the Berkshires.

AvantStay provides a personalized hospitality experience to elevate your stay. With our Concierge Service, guests have access to our tech-enabled services like fridge stocking, private chefs, massages, transportation, special occasion celebrations, baby gear rentals, ski gear, beach gear, and more. For anything you need, we’re at your fingertips!

A visit to the Berkshires in western Massachusetts is a treat for anyone looking to pair stunning rural landscapes with an exciting cultural and culinary experience. The abundance of mountains, lakes, and woods provide a wide range of outdoor activities, from rafting and fishing in the summer to skiing and tubing in the winter. Stunning at any season, this New England region is also famous for its farm-to-table food scene and local breweries. Come see for yourself!

Local Attractions: Berkshire Botanical Gardens, Bidwell House Museum, Mahaiwe Performing Arts Center, Norman Rockwell Museum, Hancock Shaker Village, Historic Deerfield, Jiminy Peak Mountain Resort

*Home Truths:*
- The dock is seasonal, it must come out of the water in fall & winter, like most docks on the lake, because the ice may permanently damage the docks.
- We allow service animals at this home. If undisclosed pets are brought into the home without AvantStay's approval there is a fine of $500 per pet.
- The driveway is paved and steep, making it suitable only for 4WD/AWD vehicles, particularly in winter months.
- Please note our occupancy includes an additional two beyond bed count. Trifold floor mattresses and additional linens can be provided upon request.
- This home is located in the Berkshires, so you may encounter wildlife such as bugs and insects.

​​​​​​​Parking Details:
Driveway space for 2 cars to park, and parking on the other side of the road, ~6 spots total
​​​​​​​
This home comes with a pack n' play travel crib available. A high chair can be provided upon request with at least 24hrs advanced notice. Just ask and we are happy to accommodate you and your little ones!

---

The room configuration is as follows:

Primary Bedroom / King bed
Bedroom 2 / 2x bunk beds
Bedroom 3 / King bed
Bedroom 4 / King bed
+ 2 twin size tri-fold sleeping mats

---

This is a smoke-free property. Violation of the no-smoking policy will result in forfeiture of the security deposit, a $300 smoking fee, and liability for any fire or property damage costs.

As part of our commitment to being good neighbors, occupancy limits and quiet hours (9pm-8am) are strictly enforced. No speakers or sound systems will be provided for use in our properties. Violation of any noise ordinances will be subject to fines that can reach up to $10,000 per violation.

Events or parties are not allowed without prior written approval and an additional fee. Any unauthorized parties or events will be shut down and a fine will be assessed. Please inquire for more information about our event policies and fees.

There is nothing more important to us at AvantStay than the health, safety, and experience of our guests & staff. We've enhanced our cleaning and sanitation protocols and are taking extra care to disinfect all surfaces between reservations with hospital-grade disinfecting solutions.

As a reminder, we do work with 3rd party vendors to maintain the property, and although we adhere to the strictest CDC guidelines and advise all contractors to wear PPE equipment, we can not always enforce. We strongly advise guests to please deny access if any vendors fail to meet and adhere to these standards.

IDs will be requested for verification after booking. All bookings over 30 days require a security deposit.

We report and prosecute all Credit Card Fraud.

​​​​​​​Tax #C1148950976

- "The house was just beautiful even though getting there was a bit tricky in the winter!! There are two ways to access the property, sometimes Google is not your friend!! The special touches were definitely the hot tub and sauna. The beds and pillows were wonderful with top end linens. The only problem we encountered was a relatively small hot water tank, no more than 2-3 people could get in a hot shower without waiting for the tank to fill up again. Would love to visit in the summer to tske advantage of the beautiful lake!!"

Location and Design - Newly renovated by the owners, Interior Designer & Architect, 5 min from Butternut Ski mountain and 20 min from Catamount and 15 min from the vibrant town of Great Barrington, the house is on Lake Garfield, and 5 min walk from a sandy white beach (Public) with the perfect setting to keep all 12-14 guests comfortable and relaxed. The house impeccable serene design will elevate your vacation experience. The space is flooded with natural light from its windows and skylights (With lake view, and 5 min walk to Lake Garfield private white sand beach and access to variety of activities the Berkshires has to offer and the proximity to the town of Great Barrington- your time will be full with excellent choices. The house can comfortably accommodate up to 14 people. 5 Bedrooms, 4 full Bathrooms, 2 Living Rooms with 2 oversized smart TV’s, 2 washing and 2 dryer machines, all quipped Chef Kitchen, Dining Room and Front & Rear Decks. The beautiful property includes a Front and Rear yards with outdoor Hot Tub & Solo smokeless Fire pit. Topped by easy walk to lake Garfield white sandy white beach, boat launch access, picnic tables and lifeguard. Our guests are welcome to use our Kayak & puddle board that are stored by the the public beach during the season. Access to the lake is ONLY through the Public Beach, located 5 min. walking distance from the house.

- "We enjoyed staying at the house with our friends/family. Easy check in, Shay was very attentive to any questions, and the check in directions were seamless. House was clean and fun for all. Also, about 10 minutes to Ski Butternut, 30 min from Catamount, and 15 to drive into town! Overall, 5 star stay!" - "Property was just as pictured. Great layout to accommodate large and small groups. Felt very luxurious. Great location. We will definitely book again."

Escape to a renovated barn that blends rustic charm with modern comfort. Enjoy airy, open spaces with vaulted ceilings and exposed beams, cozy living areas, and a small kitchenette. Relax in the open living room or unwind out on the patio. Outside, soak up peaceful views, sip a morning coffee, or stargaze at night. Perfect for a quick getaway or an extended stay, this serene barn offers a cozy escape from daily life—an ideal spot to recharge, reconnect, and create lasting memories.

Things You’ll Love
– Berkshire Vacation Rental standard: coffee, creamer, linens, towels, and toiletries.
– Fully equipped kitchen, outdoor grill, free Wi-Fi, and air conditioning for a comfortable stay.
– Spacious patio and backyard to relax and enjoy the fresh Berkshire air.
– Convenient location close to hiking trails, cultural attractions, and charming downtowns.

Nestled in the heart of the Berkshires, this barn retreat offers easy access to some of the region's best attractions. Just a minute’s drive from the Monterey Town Beach, the property is perfectly positioned for both relaxation and adventure. Explore the world-renowned music and cultural performances at Tanglewood, hit the slopes at Butternut Ski Area, or take in the stunning natural beauty of the Appalachian Trail. For a charming day out, head to downtown Great Barrington, where you'll find an array of boutique shops, art galleries, and delicious dining options. If hanging back at the house to work on that next novel is your thing, we've got the perfect perch for that too!

The Berkshires is a destination with something for everyone, from vibrant arts festivals to peaceful outdoor experiences. Whether you’re here to hike, ski, or simply unwind, this retreat is your ideal home base.

**There is no lake access directly from the barn, but the town beach is just 2-3 minutes away by car. The barn shares more than an acre of charming New England landscape with an adjacent owner’s main house, surrounded by trees on three sides

Kitchen • Barbecue/Outdoor Cooking • Balcony/Terrace • Tv • Bedding/Linens • Parking • Other • Security/Safety • Internet • Fireplace/Heating • Pet Friendly • Air Conditioner

Welcome to our charming lakeside cottage on Brewer Pond, the tranquil extension of Lake Garfield, with a neighboring standalone barn/rec room! If you're seeking a serene getaway with an array of outdoor activities, this is the perfect spot for you.

Whether you're an adventure seeker, nature lover, or simply wish to unwind in a peaceful environment, our cottage has something special to offer for everyone.

Stunning Lake Views: Start your day with breathtaking views of the shimmering waters right from the comfort of the cottage. Enjoy the stunning sunsets while sitting on the private deck or around the fire pit in the evenings.

Water Activities: Embrace the wonders of Brewer Pond with our provided kayaks & canoes. Paddle along the peaceful waters, explore the hidden coves, and immerse yourself in nature's beauty. Fishing enthusiasts will find the pond teeming with various species to catch. Make sure to say hi when paddling past the local beaver lodge!

Biking Adventures: Discover the surrounding area on two wheels. We have bicycles available for your use, making it easy to explore the nearby trails and scenic routes.

Rec Room: For some indoor fun, head to the rec room equipped with board games, a dart board, and other entertainment options. It's an ideal spot for friendly competitions and family bonding.

Cozy Living Area: After a day of exploration, unwind in the comfortable living area. Kick back on the plush sofas, watch your favorite shows on the flat-screen TV, or simply enjoy the company of loved ones. Feel free to enjoy the library of books at your convenience!

Outdoor Dining: Savor your meals in the great outdoors under our beautiful pergola, perfect for enjoying the fresh air and lovely lake views.

Pet-Friendly: We understand that pets are part of the family too! Well-behaved furry friends are welcome to join your lakeside retreat.

Nearby Attractions:

Lake Garfield Beach: Enjoy a larger sandy beach area for swimming and sunbathing just a short distance away.

Tanglewood: Experience live concerts & shows from the best that the Berkshires has to offer!

Butternut: less than 10 minute drive away for the Berkshires favorite family ski mountain

Berkshire Theater Festival: Enjoy Summerstock theater for all your summer plays

Jacob's Pillow: The go-to Berkshire spot for modern dance!

- "Very relaxing stay at Jake’s property! Perfect for a getaway to the Berkshires. Jake was a very responsive host and made the stay simple from check in to check out. Easy access to Lake Garfield and Great Barrington. "

LIVING ROOM: Bright light and high ceilings with new couch, chairs, Sonos speakers, and more.
KITCHEN: Fully-outfitted kitchenette with new butcher block counters, Samsung appliances, and table for four.
PRIMARY BEDROOM: New queen bed, wooded views, refurbished mid-century teak dresser.
LOFT BEDROOM: New double bed in loft above living room.
BATHROOM: New vanity, countertops, and shower with great water pressure
PROPERTY: Make the most of the outdoors in a new outdoor shower, bbq on a new Weber grill, roast s’mores around the fire pit, and play horseshoes, bocce, or corn hole surrounded by nothing but nature on 3 secluded acres
LOCATION: Enjoy the heart of the Berkshires in just minutes to hiking, biking, swimming, farmstands and more. Drive to Great Barrington (20 mins), Stockbridge (20 mins) and Lee (20 mins) for dining, bars, shopping, and more. Check out live music at Tanglewood (30 mins), arts at Jacob’s Pillow (20 mins), shopping at Lee Premium Outlets (20 mins), or spa & wellness at Canyon Ranch or Miraval (25 mins).

A few important details to highlight before booking:
- No washer/dryer but there are laundromats in Otis (10 mins) and Great Barrington (15 mins) with self-serve and wash-and-fold options
- No AC but new ceiling fan in living room and several standing/table fans available if needed
- No closet but there is a large chest of drawers
- Handrailing has since been installed on the main entrance.

Cottage is 510 square feet (including loft).

- "Very clean and sweet cottage that was exactly what I needed!"

Our incredible 4 bedroom log cabin is situated on 2 beautiful secluded acres in picture perfect Monterey - the ultimate Berkshire county getaway, with modern kitchen, screened porch, 2 fireplaces a fabulous outdoor hot tub and a beautiful brook on the property. Enjoy your time hiking in close by Beartown State Forest and on the Appalachian Trail or kayaking and swimming down the road in the incomparable Lake Garfield. We are a quick ride to Tanglewood, Lenox and Great Barrington & Butternut.

- "This cabin is very well-maintained with all the amenities you could ask for... especially no cable TV, and the owner David is responsive and pleasant! It is the perfect place to unplug, unwind and reconnect with life, nature and whoever you're traveling with. The house is an easy 30 minutes to Tanglewood and 20 minutes to Great Barrington so there is plenty to see and do without feeling like always being in the car. We got takeout from a delicious Thai restaurant (Siam Square) in Great Barrington one night, and on another, incredible tapas and wine at Brava in Lenox before an evening concert at Tanglewood. We highly recommend staying here."

Summary:
Nestled into more than 8 acres of pristine, private forest above the northwest section of Lake Garfield in Monterey, Hupi House blends classic New England farmhouse architecture with contemporary amenities. This serene retreat is a quick drive to nearby towns and the best outdoor activities the Berkshires have to offer, but far enough away to provide tranquil privacy. Whether you’re here with family or friends, for vacation or a work getaway, you’ll find everything you need in this cozy home.

The Space:
This 2,700-square foot house is perfect for families or friends seeking to get away from it all. With two, distinct private bedroom areas separated by the main floor, adults and kids (or families with young children) can all enjoy their own experience. Adults can find peace and quiet in the top floor suites, which consist of separate king and queen bedrooms; the lower level features a king bedroom, and a kids bedroom with two, twin bunk beds that can sleep a total of four. Each bedroom area has its own full bathroom; the house also features an additional full bath on the main floor, for additional privacy and convenience. All bedrooms feature comfortable memory foam mattresses and crisp white sheets from Brooklinen.

The main floor is ideal for group gatherings with a large foyer, a recently remodeled kitchen, a screened-in patio with a cozy breakfast table, separate dining room, and a spectacular living room with a fireplace, books galore, and stunning views of the forest and mountains beyond.

Other amenities include recently refinished wood floors, state-of-the-art mini-split air conditioning, ultra-fast WiFi with a fiber optic connection, a cozy den with a 55-inch television connected to a Roku sound bar, washer and dryer, and a Weber charcoal grill.

Guest Access:
The entire house is reserved for your enjoyment. If there is anything you need during your stay we are available via phone or your booking channel!

The Neighborhood:
The house is nestled into a tranquil, wooded hill above Lake Garfield: enjoy easy, un-trafficked walks along Hupi Road toward Beartown State Forest, or hikes through the woods on the property to the secluded pond down below. The town beach on Lake Garfield is just a five minute stroll from the front door and the charming village of Monterey with its general store and post office is only a mile away. Enjoy family skiing at Butternut (a 10-minute drive), shopping and dining in Great Barrington (a 15-minute drive), or the outstanding cultural offerings, parks, and restaurants in the southern Berkshires region. We provide plenty of recommendations in our house guide.

Other Things to Note:
We look forward to welcoming you soon!
Standard rules like no smoking, no partying and no pets allowed and being respectful of the neighbors apply.

No sweat on accidental & reported damage! Your rental includes an accidental reported damage waiver fee up to a maximum of $800. The cost to repair any accidental and reported damage to the rented property including any missing or broken items up to a maximum of $800 will be covered at no charge to you as long the damage is reported to your Host before you depart.

- "Hupi House was the perfect location for our girls reunion weekend. It was a great mix of a quiet retreat in nature and good meals/shopping in town. The property and house are beautiful and updated. Beds and linens are top notch! Highly recommend."

Enjoy our comfortable, cozy, fully furnished two-bedroom, two-bathroom ranch (1,500 square-feet) in the Berkshires (Monterey MA) with private dock access to Lake Garfield and 15-minute drive to Butternut Ski resort. Available October-April. Perfect for weekend getaway during autumn and ski season. Can sleep up to 4 people (one large bedroom with double bed, smaller bedroom with single bed and pull-out bed). Open-plan kitchen with adjoining dining area. One car garage and porch. Propane and electric heating. Three-month minimum.

Guest Services • Other • Wellness Facilities • Laundry • Balcony/Terrace • Tv • Kitchen • Security/Safety • Internet • Skiing • Fireplace/Heating • Child Friendly

We have done all we can to think of everything to ensure a great stay. Please review and let us know if you have any questions.

****As Far as the House - It is beautifully renovated and designed. And having rented in the area before we bought the property, we believe we have thought to include ever appliance and comfort you would need.

****For Summer - The central air conditioned home rests on 5 acres, with beautiful private trails, littered with blackberry bushes, two fire pits, and a large red barn that was built in the 1800s. The property stretches to Lake Garfield, where a large private dock, large floating dock, and a host of boats and kayaks are available for your personal, private use. In addition to the lakefront, a large private deck, with chairs, tables, and hammocks overlook Lake Garfield for an amazing view. The house is also open to dogs and the property also has a large, private gated dog track.

****For Winter - The house is both 5 miles away from both Butternut and Otis Ridge and about 15 miles from Catamount.

This newly renovated, waterfront property and home uniquely combines an ideal Berkshire location for privacy, land, and comfort, and fun.

Simply put, it will be very tough to find another property in the Berkshires that includes private lakefront access with such acreage.

Its size, layout and amenities can provide either the comfort for relaxation and can be an ideal setting for large families.

On the first floor of the house, guests will find a beautiful living room, designed for relaxing, playing games, or watching movies. The centerpiece of the room is a fieldstone fireplace. The first floor also features a dining room that seats 10, a gourmet kitchen with every amenity you can think of, a lighted screened in porch, and a wrap-around outdoor porch.

On the second floor, guests will find a master bedroom and private bath, two separate guest rooms with additional bathrooms, and a bunk room designed for children that can sleep six.

Outside, a large barn, originally built in the 19th century, overlooks the property. Guests will have the unique opportunity to enjoy both a beautiful lake and 4 acres of property with specially designed gardens and paths that lead to private access to Lake Garfield.

The Lakeside of the property includes a wonderful private deck with a masterful view, a private dock with canoes, a floating swimming dock and lots of water toys.

It should be noted that Lake Garfield is the most beautiful lake in the Berkshires because it is the only one managed for weed control. The water is lowered each winter to kill off the weeds, so the water is clear and weed free.

The property is located in the quaint village of Monterey, MA, which includes the oldest General Store in the County, a Post Office, a town beach, playground, a wonderful library that hosts events throughout the year, a just built community center, and wonderfully kind people.

The property is 15 minutes from the restaurants, galleries, shops, concerts and theaters of Great Barrington (rated one of “the coolest small towns in the U.S.A” by Budget Travel magazine).

The property is also 15 minutes from the towns of Lenox, Stockbridge, and Lee. In the summer, you can enjoy Tanglewood, Jacob’s Pillow, Shakespeare & Company, the Berkshire Theater Festival, Williamstown Theater Festival, the Norman Rockwell Museum, Edith Wharton’s home and numerous other cultural attractions.

The house is also a very quick drive to top-notch hiking and outdoor spots such as the Appalachian Trail and Beartown State Forest.

In the Winter, the house is located only minutes from the ski areas of Butternut, Otis Ridge, and Catamount.

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- "This is a really beautiful property." - "Beautiful property! Stunning pollinator gardens and meadows. Room for pups to run. Short walk to lake. Nice dock and plenty of lake toys. Enclosed porch was a dream. Enjoyed time with family in dining and living room as well as games on porch. Great for stargazing. Owners provided detailed information in advance for most questions we usually have which made the stay simple. Made beautiful memories!"