Cozy Cottages in The Berkshires

Best Cottage Rentals in The Berkshires

Experience the beauty of The Berkshires with our selection of delightful cottages, perfect for travelers seeking tranquility and style. Each listing promises a unique getaway experience.

Cottages in The Berkshires
Berkshire Cottage in Gorgeous Setting!
House
100 Town Beach Road, Richmond, MA, MA 01254, USA

Berkshire Cottage in Gorgeous Setting! is a sustainable vacation home in Richmond, 6.8 miles from Tanglewood Musical Center. This property encourages guests to embrace nature with its eco-friendly arrangements. Private parking is available on site at this recently renovated property. Cranwell Spa & Golf Club is 11 miles from the vacation home. With free Wifi, this 2-bedroom vacation home offers a flat-screen TV, a washing machine, and a fully equipped kitchen with a dishwasher and oven. Towels and bed linen are offered in the vacation home. For added privacy, the accommodation features a private entrance. Guests can relax in the garden at the property. Tanglewood is 7.2 miles from the vacation home, while Norman Rockwell Museum is 11 miles from the property. The nearest airport is Albany International Airport, 48 miles from Berkshire Cottage in Gorgeous Setting!.

Amenities:

Parking • Internet • Air Conditioner

Cottages in The Berkshires
Entire cottage in Berkshire Villiage
Cottage
Lanesborough, Massachusetts, USA

With close access to the Ashuwillticook rail trail and a short drive to convenient shopping and restaurants, this is a perfect location for your Berkshire getaway. Relax on the private back porch, or in the large bath tub. Cook meals in the full kitchen, or do some writing at the desk with views of the pond. Sleep in late in the king sized bed, and then enjoy what the Berkshires has to offer! 5 minute drive to Lakeview Orchards, 20-25 minutes from Lenox, Tanglewood, and Kripalu. 30 minutes to Mass MoCA and the peak of Mount Greylock (less to the start of the trails, if you want to hike it yourself!). 5 minute drive to Jiminy Peak, 45 to Berkshire East and Butternut ski resorts. 20 minutes to Notchview for cross country skiing.

This is a unique old house, and you will find nautical books and artifacts, as well as trinkets from around the world. Please note that there is no TV. The spiral staircase is one of my favorite features of the house, but it is narrow and steep, so please take care. If there will be more than two guests, and you require complete privacy from those staying on the couch downstairs, you might want to rethink, as the house is small and the bedroom upstairs is a loft. The bedroom upstairs has low ceilings - but with a comfy king sized bed, there's no need to stand up for too long, anyhow! In addition to the full bathroom downstairs, there is a half bath on the second floor, so one does not have to navigate the small staircase after bed time. The second bed, a pull out couch downstairs, is queen sized and very comfortable.

Guest Reviews:

- "The cottage was clean and as described. The street was very quiet." - "This property is located near some great hiking, biking and swimming and is a great place to stay. If we had a question it was responded to in a very timely and professional manner. The owner made us feel more than welcome and went out of their way to make our stay exceptional. I would certainly stay here again!" - "We had a very enjoyable stay. The owner provided some basics such as coffee, tea and spices. The first level consists of the kitchen, living/dining room combo. There is a narrow spiral staircase to the bedroom which has access to a toilet and sink. We didn't stay up there as the pitched roof is too close to the bed and it was cold. The bathroom has a nice washer/dryer however the baseboard heater doesn't provide enough heat so it felt frigid. There is spa tub suitable for soaking but if you less agile you may have trouble getting into the tub. The living room couch opens to a double bed with linens in the storage part of the couch. There was good heat on the first level and the hot water heats up quickly. The house is situated close to Target and the Regal Berkshire movie theatre. It is 15-20 minutes to area attractions such as Edith Wharton's house, Ventford Mansion, Norman Rockwell Museum and Clark Art Institute, etc. We would stay here again."

Cottages in The Berkshires
Picturesque Cottage with Sunroom on Ashmere Lake!
House
Hinsdale, MA, USA

Picturesque Cottage with Sunroom on Ashmere Lake! is located in Hinsdale, just 18 miles from Cranwell Spa & Golf Club and 18 miles from Tanglewood Musical Center. This vacation home provides air-conditioned accommodations with a patio and free Wifi. The Clark Art Institute is 29 miles from the vacation home. The vacation home features 3 bedrooms, a fully equipped kitchen with a dishwasher and an oven, a washing machine, and 2 bathrooms with a hair dryer. Towels and bed linen are provided in the vacation home. The property has an outdoor dining area. Tanglewood is 18 miles from Picturesque Cottage with Sunroom on Ashmere Lake!, while Norman Rockwell Museum is 24 miles away. Bradley International Airport is 53 miles from the property.

Amenities:

Other • Internet • Oceanfront • View • Sports/Activities • Guest Services • Security/Safety • Parking • Ocean View • Fireplace/Heating • Private Beach

Cottages in The Berkshires
Luxury Vacation Rental in the Berkshires!
Cottage
465 Stratton Rd, Taconic, Williamstown, MA, 01267, USA

Located in Williamstown, this welcoming cottage brings it all within your reach. Jump into your car and make short work of the 4-minute drive to Mount Greylock State Reservation or the 4-minute drive to Colonial Plaza (and enjoy the property's convenient onsite parking in the meantime).

Relax on the patio (enjoy the telescope!) or sip a drink by the firepit of this cottage. For a change of scenery, come inside and enjoy the free WiFi and TV.

This 3-bedroom, 3-bathroom rental features a living room, a BBQ grill, a fireplace, and air conditioning. The kitchen is equipped with a microwave, cookware, and a blender. And there's a washing machine, so you can even pack a bit lighter.

Amenities:

Balcony/Terrace • Sports/Activities • Internet • Tv • Laundry • Kitchen • Security/Safety • Entertainment • Child Friendly • Other • Fireplace/Heating • Air Conditioner

Cottages in The Berkshires
The Cottage
Bed & Breakfast

Situated on two acres of hills and forest, this Stockbridge B&B offers free Wi-Fi, free breakfast and stunning views of the surrounding Berkshire mountains. The Stockbridge town centre is just 2 km away. Each suite at The Cottage features a cable TV and a seating area with a sofa, as well as a small refrigerator, microwave and coffee maker. En suite bathrooms include free toiletries. Guests are provided with a private entrance to their suite as well as an outdoor patio with a dining area. An on-site terrace and garden offers another spot to relax.Mount Greylock is 45 km from The Cottage. The Norman Rockwell Museum and Stockbridge Golf Club are within 3 km from The Cottage, which is just 3 minutes’ drive from the site of the Tanglewood Music Festival. Butternut Ski Resort and Bousquet Ski Area are both less than 16 km away, while Jiminy Peak Mountain Resort is 38.3 km away.

Amenities:

Breakfast • Oceanfront • Ocean View • Balcony/Terrace • Private Beach • Kitchen • Smoking • Wheelchair Accessible • Air Conditioner • View • Parking • Pet Friendly

Cottages in The Berkshires
Cozy Becket Cottage Escape w/Lake Access!
Cottage
Becket, Massachusetts, USA

Nestled in nature and surrounded by wildlife, this Becket vacation rental offers the perfect setting for your dream outdoor escape! At this 2-bedroom, 1-bath cottage, you can wake up to birds chirping and enjoy your morning coffee on the screened porch, then boat on Pontoosuc Lake, hike beautiful trails in Otis State Forest, or attending the Jacob's Pillow Dance Festival. And don't forget to fire up the charcoal grill for a delicious barbecue!

-- THE PROPERTY --

MassTaxConnect ID: C0442280220 | Fire Pit (Wood Provided) | Fall Leaf Peeping (Best First 2 Weeks of October) | Near Crafts Fairs, Antique Shops & Tanglewood Music Festival

Bedroom 1: Queen Bed | Bedroom 2: Full Bed | Living Room: Queen Sleeper Sofa | Additional Sleeping: Crib (Available Upon Request)

COMMUNITY AMENITIES: Lake access
OUTDOOR LIVING: Charcoal grill (starter charcoal provided), screened porch, lake access, outdoor dining area, deck
INDOOR LIVING: Smart TV, DVD player, dining table, shower, books + board games
KITCHEN: Refrigerator, stove/oven, microwave, coffee maker, toaster, blender, cooking basics, dishware/flatware
GENERAL: Free WiFi, complimentary toiletries, linens/towels, hair dryer, hangers, iron/board, laundry detergent, trash bags/paper towels, space heaters
FAQ: No A/C
ACCESSIBILITY: Single-story home, stairs required to enter
PARKING: Gravel driveway (2 vehicles)

-- THE LOCATION --

HIKING TRAILS: Otis State Forest (4 miles), Tolland State Forest Campground (11 miles), October Mountain State Forest (13 miles), Appalachian Trail (14 miles)
TEE TIME: Greenock Country Club (12 miles), Bas Ridge Country Club (17 miles)
MUST-SEE SPOTS: Jacob's Pillow Dance Festival (2 miles), Green Water Pond (6 miles), Naumkeag (16 miles), Tanglewood Music Festival (17 miles), Berkshire Botanical Garden (18 miles), Berkshire Museum (22 miles), Pontoosuc Lake (23 miles), Berkshire Rivers Fly Fishing (23 miles), craft fairs, antique shops, fall foliage spots
AIRPORT: Bradley International Airport (41 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 single-story home requires stairs to enter
- NOTE: This property has fans but does not offer air conditioning
- NOTE: There is a crib available upon request. Please inquire prior to arrival if you need a crib during your stay
- NOTE: The Berkshires have great fall colors, apple picking, and pumpkin picking. The fall foliage is at its best in the first two weeks of October

Amenities:

Kitchen • Child Friendly • Laundry • Wellness Facilities • Sports/Activities • Bedding/Linens • Other • Internet • Tv • Security/Safety • Entertainment • Parking

Cottages in The Berkshires
Rustic Berkshires Cottage at Lake Buel with Kayaks!
House
New Marlborough, MA, USA

16 miles from Cranwell Spa & Golf Club in New Marlborough, Rustic Berkshires Cottage at Lake Buel with Kayaks! offers accommodations with access to a spa center. This vacation home features accommodations with a patio. Free Wifi is available throughout the property and Norman Rockwell Museum is 13 miles away. The air-conditioned vacation home is composed of 1 separate bedroom, a living room, a fully equipped kitchen with an oven and microwave, and 1 bathroom. Towels and bed linen are available in the vacation home. For added privacy, the accommodation features a private entrance. Tanglewood Musical Center is 16 miles from the vacation home, while Tanglewood is 16 miles from the property. Bradley International Airport is 42 miles away.

Guest Reviews:

- "better then expected" - "Would go back in a heartbeat!"

Cottages in The Berkshires
Charming historic cottage on scenic road to Mt. Greylock
Cottage
Lanesboro, Massachusetts, USA

If you’ve driven by, you’ve wondered about the story of this beautiful stone building. Built in 1832 as a one-room schoolhouse – a function it served until 1950 -- this charming and historic building has been given new life as a guest house - since 1998.

PLEASE NOTE: It's an old building with an unusual layout, so please carefully read the description below.

Beautifully situated amidst horse farms on the scenic road to Mt Greylock. In the center of the Berkshires, 5 miles from Jiminy Peak ski area, 10 miles from South Williamstown, 15 miles from Tanglewood and Mass MoCA, and 20 miles from Jacob's Pillow. 5 miles to Pittsfield and the Berkshire Mall. Private garden. 5 acres of property in the back where horses graze, and alpacas, donkeys and other friendly animals next door.

Everything is provided: fully-furnished mostly with antiques. Bedspreads, linens, blankets, pillows, towels, iron and ironing board. SMALL KITCHEN with mini stove/oven, refrigerator, microwave, Keurig coffeemaker with assortment of coffee, tea and hot chocolate, pots and pans, dishes, cutlery, etc. Broadband internet and TV with Netflix, Hulu and other streaming options included.

There are 2 floors. The first floor is the old classroom with old desks. There is also a trundle bed which can be used as 2 twins. The bathroom is on the first floor. The 2nd floor is like a studio apartment - with a queen bed and a twin bed and the small kitchen. PLEASE NOTE: There is one bathroom, on first floor.

Ideal for a romantic getaway or for a family of 4-5. A fee of $25/night applies for additional adults after the first two (limit of 4 adults total). No extra charge for children. Please indicate the number of children in your message to us, but select 0 children in the pull-down menu so that you are not charged.

The Old Stone School is available to rent 12 months a year. Each season has it's benefits:

SPRING - Trees arise from winter sporing their fleeting Spring green color, daffodils, tulips, hiking trails are open, enjoy the warm weather after a long winter! Calves appear on the hill behind the schoolhouse.

SUMMER - Flowers blooming, berries to pick, outdoor activities nearby, culture everywhere - Tanglewood, Jacob's Pillow, Barrington Stage, Clark Art Museum, MassMoCA, Williams College Museum of Art, etc.

FALL - Enjoy the kaleidoscope of Fall colors covering the hills behind the schoolhouse. Hike Mt. Greylock - short and long hikes. Go the top and check out Bascom Lodge - a stop on the Appalachian Trail.

WINTER - Jiminy Peak is less than 10 mins. away.Ski or snow tube at Bousquet is 20 mins. away. Cross country Ski in the fields out back or go to Hilltop Orchards in Richmond or Notchview in Windsor.

Guest Reviews:

- "Our stay at this historic schoolhouse was terrific. The owner was very welcoming and helpful. We slept well there - as the two available large rooms up and down afforded flexible sleep areas. Beds comfy. The kitchen was well equipped and the amenities such as foil, plastic wrap, tea, a Keurig machine, extra paper plates etc made our stay very convenient. The history of the place is fascinating. Many thanks!" - "This charming converted schoolhouse is well-supplied for the present day while reminding you of a bygone age. It's set among beautiful rural woods and pastures, private, but with ideal access to local attractions south, like Stockbridge and Lenox or north, like Williamstown and North Adams. The owners are extremely helpful and friendly, and they also simply allow you to enjoy your stay. A great place!"

Cottages in The Berkshires
The Mountain Cottage
Ski Chalet

Located in Florida, 46 km from Bennington Battle Monument and 24 km from The Clark Art Institute, The Mountain Cottage offers a garden and air conditioning. Featuring free private parking, the chalet is in an area where guests can engage in activities such as hiking and fishing. This chalet comes with 2 bedrooms, a kitchen with a fridge and a microwave, a flat-screen TV, a seating area and 1 bathroom equipped with a shower. Towels and bed linen are featured in the chalet. The chalet provides a sun terrace. Southern Vermont College is 44 km from The Mountain Cottage, while Bennington Museum is 44 km away. The nearest airport is Albany International Airport, 82 km from the accommodation.

Amenities:

Balcony/Terrace • Child Friendly • Laundry • Kitchen • Air Conditioner • Parking

Cottages in The Berkshires
Quiet rustic cottage with shared lake access
Cottage
New Marlborough, Massachusetts, USA

Welcome to Lake Buel! This recently renovated cottage has been an old favorite for generations since the 1950’s. Abutting a dramatic sloping hill, this unique spot offers privacy on a dead end road and is a 2 minute walk to the water. Bring your non motorized boat and park it at the shared dock or use our canoe and life jackets for your aquatic adventures. All are welcome to experience this space and the surrounding areas.

Guest Reviews:

- "This is a wonderfully simple cabin that has everything you need and nothing you don’t. It is cozy, comfortable, and charming. We were here for two days and managed to swim in the lake twice, canoe once, s’mores over the fire pit, and relax a ton. Great hosts who checked in and made sure we knew the lay of the land. We really loved this spot and will be back." - "Great place located on Lake Buel, felt welcomed immediately by amount of communication and information pre arrival. Upon arrival we were greeted by a personalized note and a treat from the owners. It was relaxing and we enjoyed the area immensely. As a native to the Berkshires It was a real joy spending time in an area that I don't often get to visit. So much history, culture, and charm."

Cottages in The Berkshires
Lake Views and Dock Access - Pittsfield Cottage!
House
Pittsfield, MA, USA

Lake Views and Dock Access - Pittsfield Cottage! is located in Pittsfield, just 12 miles from Tanglewood Musical Center and 12 miles from Tanglewood. This vacation home is 17 miles from Norman Rockwell Museum. Free Wifi is available throughout the property and Cranwell Spa & Golf Club is 12 miles away. The air-conditioned vacation home is composed of 4 separate bedrooms, a living room, a fully equipped kitchen with a dishwasher and oven, and 2 bathrooms. Towels and bed linen are featured in the vacation home. The property has an outdoor dining area. Albany International Airport is 43 miles away.

Amenities:

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

Cottages in The Berkshires
Waterfront Cottage 10 Min From Great Barrington
Cottage
New Marlborough, Massachusetts, USA

A couple's getaway for the books awaits you at this Lake Buel vacation rental. Just 6 miles from Great Barrington's shops, restaurants, and art scene, this 2-bedroom, 1-bath cottage is close to all the Berkshire's excitement, yet far enough for high-quality rest and relaxation. Hike the Appalachian Trail in the summer, ski Butternut Basin during the winter, or enjoy the fall colors from the home's charming deck - and don't forget the amazing stargazing! The ultimate Bay State vacay starts now!

The Property

Deck overlooking Lake Buel | Fire Pit | Peaceful Neighborhood | Seasonal Fishing Dock | Panoramic Views

Craft the ultimate couple's getaway at this charming lakeside cottage - close to Great Barrington dining, arts, and culture, yet rural enough for rest, relaxation, and of course, romance.

Bedroom 1: Bob-o-Pedic Dual King Adjustable Bed | Bedroom 2 (Updated 9/23/24): Bob-o-Pedic Queen Adjustable Bed

OUTDOOR LIVING: Deck, chairs, patio, gas grill, fire pit

INDOOR LIVING: 3 flat-screen TVs, DVD player, vaulted ceilings (washer/dryer available for stays of one week or more.)

KITCHEN: Well-equipped, drip coffeemaker, granite countertops, ice maker, dishware & flatware, pots & pans, stainless steel appliances, Crockpot, toaster, kitchen cart. (Countertop dishwasher available for stays of one week or more.)

GENERAL: Free WiFi, ceiling fans, towels/linens, canoe, kayaks, SUPs, life jackets

FAQ: 2 steps to access, no A/C

PARKING: Driveway (3 vehicles)

Guest Reviews:

- "Spent two nights for a winter weekend to explore all the trails. The cottage is updated and like new. Has every thing you need to cook dinners, relax and feels like a home. Owner checks in to make sure you have all the info you need and is accessible if needed. Had a great experience!!" - "The cottage is perfect... all the comforts of home & the View is fantastic." - "This location is just perfect. Quiet serenity for a perfect weekend getaway. The cottage is nestled among the trees and has water access. It was clean and well appointed. Cathy was very accessible. We will be back!!"

Cottages in The Berkshires
nPeaceful, Newly Renovated Lakeside Cottage On Lake Garfield In Berkshires
Cottage
Monterey, Massachusetts, USA

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.

Guest Reviews:

- "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."

Cottages in The Berkshires
Charming Cottage, New Marlborough Village Green in the Berkshires
Cottage
New Marlborough, Massachusetts, USA

The Cottage apartment is located in the Village of New Marlborough, Ma.
We are on the Village Green. Across the road from the famous Old Inn On The Green Restaurant. Also down the road from Gedney Farm, lodging and restaurant. Beautiful restored barns are used for many weddings
15 minutes from Butternut Ski Basin. 20 min. to town of Great Barrington.
1/2 hour to Tanglewood & Jacobs Pillow.
The apt. looks out onto a beautiful field from the kitchen.
There is a main house which is separate from the cottage. The cottage sleeps 4 comfortably. Parking in front of cottage.

Cottage in a beautiful setting: The Cottage is located in Historic New Marlborough Village Green. The 4 Star Zaggat rated Old Inn on the Green is a walk across the road. Many beautiful lakes & streams in the area. Gallery at the Historic Meeting House holds many events during the summer season.

Cross Country Sking in fields. Butternut ski resort 15 from cottage. Great Barrington for local town eatery & movies 20 minutes from cottage.

Guest Reviews:

- "We arrived at night, so we didn't get to see the extraordinary back yard until we awakened the following morning. it was so divine to just sit there and see all the lush greenery. owners had thoughtfully left great coffee and some breakfast fixings which was so appreciated. Maria was a lovely host." - "Beautiful cottage that has been well renovated and best backyard view. Directly across the road from the Old Inn at New Marlborough which is where the wedding event was. Maria helped with trusted recommendations on where to eat etc. her property is highly recommended."

Cottages in The Berkshires
Romantic Berkshires Cottage - Stunning Views, Pool
Cottage
Great Barrington, Massachusetts, USA

This unique cottage--30' away from our home on a fenced, three-acre property--has its own entrance and its own parking space. The pool is shared with us, but you will have it to yourselves for most of the day--just ask for private time.

There are windows on three sides, a ceiling fan and a window fan.

The Berkshires in spring, summer and fall are alive with beauty, and we offer glorious views of the rolling hills and verdant meadows. Nature lovers, artists, writers and all who cherish tranquility will take particular delight in this unique spot.

Perfect for any couple (can accommodate a small child, too), this gem of a cottage offers a romantic break that will appeal whether you are an active hiker or biker, or just want to sit under the trees or by the pool with a good book and savor the unsurpassed scenery. You'll be on a secluded country lane, but only minutes from downtown Great Barrington with its restaurants, music, theater and shopping. It's an easy drive to all area attractions and great Appalachian Trail hikes. The area roads are also ideal for biking.

Bedroom/sitting room, kitchenette with toaster oven, electric kettle, toaster, microwave and full-size fridge, but no stove. Full bath with bathtub and shower. Non-smoking only. Check our rates for week-long specials.

We do not accept reservations for longer than two weeks.

We can also assist you in finding just the right activity for your stay, whether it's hiking the state's highest peak, Mt. Greylock, a picnic at Bartholomew's Cobble or just lounging on the bench outside the cottage.

Studio offers complimentary bottle of wine, use of two kayaks, excellent wifi coverage, hair dryer, onsite parking, TV, microwave, electric kettle, Ninja coffee maker, toaster, toaster oven, full-sized fridge.

Please note that taxes of 11.7% include 6% Great Barrington tax and 5.7% Mass. tax.

Guest Reviews:

- "My husband and I had a wonderful stay at Frederica's guest house! The 'French country' vibe instantly made us feel at home. The pool and grounds were even more stunning than the photos. The highlight was definitely the pool area and the beautiful grounds. The relaxing atmosphere and natural surroundings provided the perfect escape! We were pleased to bring our two golden doodles along, although the on-leash requirement was a bit restrictive. Nonetheless, it didn't significantly impact our overall enjoyment. In summary, Frederica's guest house offers a charming retreat with its cozy interior, breathtaking pool, and tranquil ambiance. We appreciate Frederica for sharing this lovely space with us and look forward to returning in the future. If you are thinking about booking this vacation home, go ahead and do it! You'll have a great time!"

Cottages in The Berkshires
Perfect Vacation Get Away - Historical New Marlborough
Cottage
New Marlborough, Massachusetts, USA

Quaint cottage in Southern Berkshire nestled in the historic district of New Marlborough. Cottage sits on 3 acres all of which is well maintained. Available for the fall foliage season. Full kitchen and bath. Sleeping area in loft sleeps two. Queen size sleeper sofa serves as additional sleeping for guests. Cottage surrounded by 1,000 sq ft cedar deck on 3 sides. Goshen stone patio and grilling area. 140' rock wall accentuates the property. Cottage is walking distance to Inn on The Green and New Marlborough Grange. 5 minutes to Butternut Ski area. Land trust across the street from cottage. Outdoor smoking only. Culligan water sulfur filtration tank provides clean water with no smell to the entire house. The stairs to the upstairs bedroom can be challenging to for older people or people with physical limitations.

Guest Reviews:

- "Cute cottage and great property. Enjoyed how quiet it is when we spent time on the patio enjoying our breakfast and dinners. Well equipped cabin exactly as advertised!" - "Good kitchen to make our breakfast The hatch getting up to the bedroom was interesting, be sure your good w a ship’s ladder. Thoroughly enjoyed our stay, I’d return anytime And loved the wood stove! Always had a fire crackling.." - "We have 2 dogs and it is hard to find somewhere that we can bring them both on vacation. They were both welcomed and loved running around the huge yard. We enjoyed the wrap around porch and the cozy, homey feeling of the cottage. The host, James, answered very promptly when we had questions. We would definately like to go back again."

Cottages in The Berkshires
Berkshire Mountain Cottage: in the Heart of the Berkshires
Cottage
Great Barrington, Massachusetts, USA

Berkshire Mountain Cottage is a warm and cozy hideaway located in the Berkshire hills. Its located between North Egremont and West Stockbridge, placing it within 15 minutes of Tanglewood and 5 minutes from Main Street in Great Barrington, by car, and close to many other Berkshire locales. The cottage is also very close to hiking and biking trails and numerous swimming areas on both lakes and rivers.

The cottage features (2) bedrooms, living room, kitchenette, screened in porch and (1) bathroom. The master bedroom contains a Queen sized bed and plenty of closet space. The second bedroom has a trundle bed with a riser and it sleeps (2). The building is semi attached to the main house. It has a separate entrance. And private outdoor area It is a roomy 800 sq ft, recently renovated, and beautifully decorated. You can easily prepare a great breakfast, lunch and even dinner (BBQ) or choose to sample one of the many restaurants in Great Barrington.

The cottage property contains grassy areas, flower gardens, forest, a stream, and a beaver pond which attracts exotic birds. There are tables and chairs set up outdoors for your enjoyment. We welcome well behaved dogs of all sizes.

In these special days we are taking special measures to keep everyone healthy.
All guest reservations are spaced 1-3 days apart when possible, to allow airing, and cleaning
We take special care of cleaning and sanitizing the cottage prior to your arrival.
All linen and towels are washed at a high temperature, and dried in high heat.
We change all linen, including duvet cover for each guest (European style).
Cleaning is conducted with masks and gloves.

Keywords: Cottage

Guest Reviews:

- "The Cottage is exactly as described, comfortable for 2 people, artfully decorated, delightful. The hosts are warm and welcoming, attentive, but not intrusive. The location is quiet and lovely. A welcoming bottle of wine set the tone for the stay. We plan to return. 5+ stars!" - "it is just a cottage, very clean and comfortable. kitchen was a bit inadequate for us as it has no stove and not much counter space and a small sink. Outside property was very spacious and beautiful."

Cottages in The Berkshires
Lakefront Cottage In The Berkshires In Western Massachusetts
Cottage
Becket, Massachusetts, USA

INSIDE
650-square foot charming cottage directly on 129-acre Center Pond in Becket, MA. One main bedroom upstairs with queen bed, very small loft area upstairs (for sleeping only - probably best for children) with 2 mattresses, small bedroom downstairs with single bed. Sleeps 3 in beds, plus the loft beds for kids and a loveseat-sized couch. Small kitchen with full oven, microwave, frig. No dishwasher. Small bathroom with shower. No washer/dryer. No cable TV, but large TV monitor and blue ray DVD player. High-speed internet. NOTE: the homeowner's association along the road has very strict quiet policy after 10 PM so this cottage WILL NOT be a good choice if abiding by this policy will be a problem.

OUTSIDE
Outside has spacious upper deck and lower deck, plus dock. Eating table and sitting area on upper deck, with comfortable seating on lower deck. Dive into water from dock into 6-foot depth. Clean, clear lake great for swimming. Cottage has 3 kayaks and one 2-person canoe. Great fishing . Motorboats permitted. However, very quiet, peaceful lake. Cottage is east facing. Warm, sunny breakfasts on the deck.

SURROUNDING AREA
Becket is located in the Berkshire Hills of Massachusetts close to great hiking (including Appalachian Trail), antiquing , outlet shopping (Lee), theatre (Stockbridge, Pittsfield), dance (Jacobs Pillow), music (Tanglewood), museums (Norman Rockwell Museum in Stockbridge, Clark Institute in Williamstown). Great biking on many of the rural roads in the area.

Guest Reviews:

- "This was our 4th time staying here, first with a kid, we enjoyed the grill, hammocks, kayaks, and of course the view from the two decks." - "This was our second stay and it did not disappoint! Beautiful, clean, comfortable home situated directly on the lake. Host was very kind and communicative. 10/10 would recommend." - "We had a lovely time at Jim's home, which sits right on this lake and is also near lots of great hiking. Small smallmouth bass and pickerel are easily caught from Jim's dock and even more easily when fishing from Jim's canoe. There may be bigger fish in there, but I can only attest to the plentifulness of the 12-inch smallmouths and pickerel. Jim communicates quickly and clearly, and we would love to come back."

Cottages in The Berkshires
Rustic Berkshires Cottage at Lake Buel w/Kayaks!
Cottage
New Marlborough, Massachusetts, USA

Bring your loved one or best friend along on a Berkshires getaway to this rustic 1-bedroom, 1-bath vacation rental in New Marlborough. Nestled 30 yards from private right-of-way access to Lake Buel, this cabin offers serenity and unbeatable views of the lake and Berkshire Mountains. Launch the 2 kayaks, hike along the Appalachian Trail, or explore the local cultural scene! Whether you’re visiting for a romantic retreat, cultural indulgence, or active outdoor getaway, this is the ideal home base.

-- THE PROPERTY --

MassTaxConnect ID C0239292030 | Pets Welcome w/ Fee | Right-of-Way Lake Access | 2 10-Foot Kayaks | Fire Pit

This rustic cottage provides simple, economical accommodations for those who want to enjoy a wonderful lake and experience Conde Nast’s 2022 pick for ‘the most beautiful place in Massachusetts!’

Bedroom: King Bed | Living Room: Queen Futon

OUTDOOR LIVING: Patio, fire pit, new patio furniture (added in 2019), 2 kayaks (Pelican Trailblazer 100XT), Weber charcoal grill
KITCHEN: Well-equipped w/ refrigerator, new gas range, drip coffee maker, tea kettle, microwave (no dishwasher - appliances are older but fully functional)
INDOOR LIVING: Brand new King-sized Simmons Beautyrest mattress (adjustable up to 80 degrees), 43" 4K Smart TV for guest's streaming services (no cable), DVD player, tables set for 2 in the kitchen & by the picture windows, beautiful lake views
GENERAL: Free WiFi (high speed), self-check-in, new shower (added in 2019), interior redecorated in 2019, new bathroom fixtures, 5000 BTU window air conditioner in bedroom & darkening window treatments for living room (all added in 2021)
FAQ: Washer/dryer NOT available, stairs required, steep stairs
PARKING: Driveway (1 vehicle, maximum length 16 feet)

-- THE LOCATION --

LAKE BUEL (30 yards away): Kayaking, floating, fishing, great swimming (summer weeds in the lake can be an impediment to swimming for some), public boat launch (3.1 miles)
HIKING: Appalachian Trail (1.6 miles), Beartown State Forest (4.7 miles), Umapchene Falls Park (6.4 miles), Monument Mountain (8.0 miles), Campbell Falls (11.3 miles), Mount Greylock (35.0 miles)
HIT THE LINKS: Greenock Country Club (9 holes,13.6 miles), Wyndhurst Manor and Club (18 holes, 15.6 miles)
ROAD BIKING: Several road biking courses provided by the host in the information brochure
ART/THEATER: Mahaiwe Performing Arts Center (6.3 miles), Berkshire Theatre Group (11.6 miles), Norman Rockwell Museum (11.7 miles), Shakespeare & Company (15.6 miles), Tanglewood Music Center (16.1 miles), Jacob’s Pillow Dance Festival (18.0 miles), Mass MoCA (44.0 miles)
SPA/YOGA: Kripalu Center For Yoga & Health (15.7 miles), Miraval Berkshires Resort & Spa (15.7 miles)
WINE & DINE: Les Trois Emme Winery (1.2 miles), Cantina 229 (4.9 miles), The Old Inn on the Green (5.1 miles), Xicohtencat (5.2 miles), Café Adam (5.9 miles), Naji’s Mediterranean Cuisine (5.9 miles), Aegean Breeze (5.9 miles), Barrington Brewery & Restaurant (6.1 miles), Number Ten (6.3 miles)
AIRPORT: Bradley International Airport (42.9 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
- Pet friendly w/ $100 fee (+ fees & taxes, maximum 1 allowed, non-shedding breeds only)
- No events, parties or large gatherings
- Additional fees and taxes may apply
- Photo ID may be required upon check-in
- NOTE: No food is provided at the property
- NOTE: Temperatures in the mountains can drop significantly beginning in mid-late September and be quite cool from early April through mid-June. While the cottage has baseboard heat and is fully insulated, guests during these periods should check the forecast and prepare accordingly
- NOTE: The property requires stairs to access
- NOTE: The property may not be suitable for young children due to the steep stairs

Guest Reviews:

- "Quiet apot even when boaters were using the lake. Had a couple of issues that were addressed quickly." - "My husband, dog and I enjoyed a long weekend here to celebrate our 8th wedding anniversary- the property was beautiful and quaint! Perfect for exploring on walks, or nearby to the Norman Rockwell museum. Would stay here again." - "Peaceful and very relaxing. Perfect for getting away from it all" - "Beautiful and clean cabin with stunning lake views. Short drive to the Great Barrington which we loved. Also the Les Trois Emme winery which was only minutes away - the wine slushie is a must! Loved everything about our accommodations and our trip to the Berkshires. "

Cottages in The Berkshires
Stay at Beaver Lodge!
Cottage
Monterey, Massachusetts, USA

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.

Guest Reviews:

- "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!"

The Berkshires Family Friendly Cottages

The Berkshires Cottages with Parking

The Berkshires Pet Friendly Cottages

The Berkshires Cottages with Entertainment

The Berkshires Cottages with Private Beach

The Berkshires Cottages with Private Pool

The Berkshires Cottages with Spa

The Berkshires Cottages on the Map

Compare the Best Cottages in The Berkshires – Addresses, Prices, Stars, Rating, and Review Count

Property Name Address Price ($) Star Rating Review Count Book
Berkshire Cottage in Gorgeous Setting! 100 Town Beach Road, Richmond, MA, MA 01254, USA 223 4.0 1 Click here
Entire cottage in Berkshire Villiage Lanesborough, Massachusetts, USA 214 3.0 9.6 8 Click here
Picturesque Cottage with Sunroom on Ashmere Lake! Hinsdale, MA, USA 491 4.0 1 Click here
Luxury Vacation Rental in the Berkshires! 465 Stratton Rd, Taconic, Williamstown, MA, 01267, USA 604 3.0 1 Click here
Cozy Becket Cottage Escape w/Lake Access! Becket, Massachusetts, USA 232 2.0 9.0 2 Click here
Rustic Berkshires Cottage at Lake Buel with Kayaks! New Marlborough, MA, USA 147 3.0 9.3 3 Click here
Charming historic cottage on scenic road to Mt. Greylock Lanesboro, Massachusetts, USA 220 10.0 117 Click here
Quiet rustic cottage with shared lake access New Marlborough, Massachusetts, USA 255 10.0 107 Click here
Lake Views and Dock Access - Pittsfield Cottage! Pittsfield, MA, USA 552 3.0 1 Click here
Waterfront Cottage 10 Min From Great Barrington New Marlborough, Massachusetts, USA 342 10.0 99 Click here
nPeaceful, Newly Renovated Lakeside Cottage On Lake Garfield In Berkshires Monterey, Massachusetts, USA 234 9.6 74 Click here
Charming Cottage, New Marlborough Village Green in the Berkshires New Marlborough, Massachusetts, USA 263 10.0 72 Click here
Romantic Berkshires Cottage - Stunning Views, Pool Great Barrington, Massachusetts, USA 254 10.0 59 Click here
Perfect Vacation Get Away - Historical New Marlborough New Marlborough, Massachusetts, USA 246 9.2 57 Click here
Berkshire Mountain Cottage: in the Heart of the Berkshires Great Barrington, Massachusetts, USA 244 9.8 49 Click here
Lakefront Cottage In The Berkshires In Western Massachusetts Becket, Massachusetts, USA 242 10.0 47 Click here
Rustic Berkshires Cottage at Lake Buel w/Kayaks! New Marlborough, Massachusetts, USA 239 9.2 44 Click here
Stay at Beaver Lodge! Monterey, Massachusetts, USA 217 10.0 43 Click here

Note: The prices for each Cottages in The Berkshires do vary. This can be because of the number of people you are booking for, how far in advance you book and the season. The prices above are only meant as a rough estimate for comparison purposes. Click the buttons above (or click here) to get the latest prices.

Frequently Asked Questions

Cottages in The Berkshires that include a pool or hot tub include:

  • Romantic Berkshires Cottage - Stunning Views, Pool.- Review Count: 59, Rating: 10.0

These cottages in The Berkshires offer spa or wellness amenities:

  • Rustic Berkshires Cottage at Lake Buel with Kayaks!.- Review Count: 3, Rating: 9.3

Family-friendly cottages in The Berkshires include:

  • Entire cottage in Berkshire Villiage.- Review Count: 8, Rating: 9.6
  • Luxury Vacation Rental in the Berkshires!.- Review Count: 0, Rating: 0.0
  • The Cottage.- Review Count: 63, Rating: 5.4

Pet-friendly cottages in The Berkshires include:

  • The Cottage.- Review Count: 63, Rating: 5.4
  • Rustic Berkshires Cottage at Lake Buel with Kayaks!.- Review Count: 3, Rating: 9.3
  • nPeaceful, Newly Renovated Lakeside Cottage On Lake Garfield In Berkshires.- Review Count: 74, Rating: 9.6

Cottages in The Berkshires that include breakfast or meal options include:

  • The Cottage.- Review Count: 63, Rating: 5.4

Cottages in The Berkshires offering on-site parking include:

  • Berkshire Cottage in Gorgeous Setting!.- Review Count: 0, Rating: 0.0
  • Entire cottage in Berkshire Villiage.- Review Count: 8, Rating: 9.6
  • Picturesque Cottage with Sunroom on Ashmere Lake!.- Review Count: 0, Rating: 0.0

Some of the best Cottages in The Berkshires are:

  • Berkshire Cottage in Gorgeous Setting!.- Review Count: 0, Rating: 0.0
  • Picturesque Cottage with Sunroom on Ashmere Lake!.- Review Count: 0, Rating: 0.0
  • The Cottage.- Review Count: 63, Rating: 5.4

Some of the popular Cottages in The Berkshires are:

  • Charming historic cottage on scenic road to Mt. Greylock.- Review Count: 117, Rating: 10.0
  • Quiet rustic cottage with shared lake access.- Review Count: 107, Rating: 10.0
  • Waterfront Cottage 10 Min From Great Barrington.- Review Count: 99, Rating: 10.0