Best Resorts in The Berkshires, MA for Your Perfect Getaway

Nestled in the scenic hills and countryside of the Berkshires in Hancock, Massachusetts, this hotel offers recreational activities. The Vacation Village in the Berkshires ideally places guests only moments away from a variety of activities, historical sites and delicious dining options. Biking trails, top-rate ski trails, fishing and swimming are all nearby. Guests can also enjoy the variety of amenities available at the Berkshires Village. The property features a state-of-the-art fitness center, private balconies and patios and fully and partially equipped kitchens. Jiminy Peak Mountain Ski Resort is 1.6 mi away from this hotel.

- "Perfect family getaway." - "This is the third time I’ve stayed here and it won’t be the last! Such an amazing place for a quick getaway!" - "Over all was a beautiful stay even though the shower was cold ." - "I love everything about my stay, particularly fireplace electric though but looks very real and super warm!" - "It was excellent as always!" - "Excellent" - "Great week all around!" - "Always a great time at VV. Grandchildren love it."

Slopeside fun with 2 restaurants and 2 bars/lounges
With direct access to the slopes, Jiminy Peak Mountain Resort makes guests feel at home with amenities like an outdoor pool, ski storage, and complimentary wireless internet access.
Each condo provides a microwave and a coffee/tea maker, plus a DVD player and a TV with cable channels. Additional amenities include a stovetop, a hair dryer, and a phone.
Jiminy Peak Mountain Resort offers 105 air-conditioned accommodations with DVD players and hair dryers. Cable television is provided. Guests can make use of the in-room microwaves and coffee/tea makers. Bathrooms include bathtubs or showers.
2 hot tubs are on site along with an outdoor pool. Other recreational amenities include outdoor tennis courts, ski-in/ski-out access, and a fitness center.

The recreational activities listed below are available either on site or nearby; fees may apply.

- "Unit was very clean and well appointed. Location was amazing. Will definitely stay again!" - "The property was great. I would say a little more cleanliness in the bathtub! Overall, amazing!" - "Staff were so attentive, even at the late hour we checked in (10pm) the place had everything you need. Amazing views and amenities. Loved it" - "charming town house condo. plenty of room and privacy for our family. Well supplied. Comfortable beds."

21 miles from Cranwell Spa & Golf Club in Hancock, Spacious 3BR 3BA Sleeps 8 Ski On Off Jiminy Mountain Resort provides accommodations with access to a fitness center. With mountain views, this accommodation features a swimming pool. Tanglewood Musical Center is 21 miles from the vacation home and Tanglewood is 21 miles away. With free Wifi, this 3-bedroom vacation home offers a cable TV, a washing machine, and a fully equipped kitchen with a dishwasher and oven. Towels and bed linen are featured in the vacation home. The accommodation has a fireplace. Guests can also relax in the garden. Norman Rockwell Museum is 27 miles from the vacation home, while Rensselaer Polytechnic Institute is 28 miles away. Albany International Airport is 35 miles from the property.

- "Wonderful condo on Jiminy Peak and Great host - Howie." - "10/10 stay for you, your family/friends and pet" - "Fantastic weekend at Jiminy Peak!" - "Howie was very accommodating. We will definitely go back the grand kids loved it." - "My family loved the comfort of your condo" - "Lovely stay for our family. Thank you!" - "The villa was in a fantastic location & had all the conveniences we were looking for our getaway🍁🍂"

Get ready for an unforgettable family escape at Wyndham Bentley Brook, where breathtaking natural beauty and year-round fun await! Nestled at the base of Jiminy Peak Ski Mountain, this two-bedroom suite provides the perfect retreat after a day of adventure, offering cozy comfort with a flat-screen TV, air conditioning, a kitchenette, and free Wi-Fi.

In the winter, Wyndham Bentley Brook is a skier’s paradise—step right outside your door and onto the lifts for seamless ski-in, ski-out access. When the snow melts, the fun continues! Explore the picturesque Berkshire Mountains with hiking, horseback riding, and outdoor concerts at nearby Tanglewood. As the seasons change, the vibrant fall foliage creates a spectacular backdrop for your outdoor adventures.

Beyond its stunning mountain setting, Wyndham Bentley Brook is the ideal home base for exploring Berkshire County’s rich cultural scene. Visit world-class museums, historic landmarks, charming shops, and restaurants that celebrate the region’s art and history. Whether you're hitting the slopes or discovering the natural and cultural wonders of the Berkshires, this resort is perfectly positioned for year-round excitement.

Why Wyndham Bentley Brook is a "Can't Miss" Destination:

- Ski-in, ski-out access at the base of Jiminy Peak Ski Mountain for the ultimate winter getaway.
- Year-round activities including hiking, horseback riding, and concerts at nearby Tanglewood.
- Close proximity to cultural attractions, museums, and historic landmarks in Berkshire County.
- Spacious two-bedroom suites with modern amenities, perfect for families and groups.

With the perfect blend of mountain adventure, scenic beauty, and cultural exploration, Wyndham Bentley Brook is your go-to destination for an unforgettable vacation in the heart of the Berkshires!

Items to note:
- The bed size in the second bedroom can vary.
-The resort will be undergoing renovations to multiple buildings from Apr. 30, 2025 through Sep. 15, 2025. During this time the Game room will be closed and detours to access to the pool will be required. You may experience noise, dust, odors and work crews. Dates are subject to change.
- Closest shopping/entertainment/additional dining: 30 minutes away
- Closest nightlife is in Albany, 45 minutes away
- Vehicle recommended to enjoy area
- A credit card is required for the $250 security deposit requested at check in.

KOALA Disclosure Summary:

-IMPORTANT: Payments appear as “KOALA VACATIONS” on credit card statements.

-BEFORE YOUR CHECK-IN: This booking requires the name and address of the person checking in. THE PERSON CHECKING IN MUST MATCH THE PHOTO ID PROVIDED TO US.

-The primary guest checking in must be at least 21 years old.

-Resorts own and manage all units/amenities; unit assignments at check-in.

-Room photos are samples; actual furniture/layout may vary.

-The Resort is responsible for maintenance, may alter/close select amenities due to COVID-19 or other factors. KOALA is only responsible for ensuring your check-in and unit category.

-KOALA is not responsible for unit condition or resort services. For resort, unit or guest related issues after check-in, please contact the resort management.

-Check cancellation policy before booking. No refunds after the cancellation deadline due to any reason, including COVID-19 (except full resort closures), natural disasters, or personal changes. For these reasons we always recommend purchasing trip insurance for unforeseen circumstances like these.

This resort is part of a timeshare and you may be invited to attend a sales presentation. Any participation is always optional and never required when booking through KOALA.

- "Overall a great spot. Ski in /ski out. Great getaway ." - "Everything was perfect for a ski weekend" - "Loved the grounds , the room , the pool . The staff was super friendly." - "Great property for a long weekend. We enjoyed the space and amenities on the property." - "Many amenities, comfortable stay. Had a great time!" - "A very pleasant, clean and quiet place to stay. The separate living space makes it very comfortable. I would have like to see that the outside doors were only accessible with the unit key. That was a security issue. Overall, a great place. Thank you."

Located in South Lee and within 5 mi of Norman Rockwell Museum, Holiday Inn Club Vacations Oak n Spruce Resort in the Berkshires has barbecue facilities and nonsmoking rooms. Featuring family rooms, this property also provides a seasonal outdoor pool, an indoor pool, a fitness center and a bar. All rooms feature a flat-screen TV, a seating area, a kitchen and a private bathroom. Free WiFi is available. Holiday Inn Club Vacations Oak n Spruce Resort in the Berkshires also provides guests with a children's playground. Adams is 25 mi from the accommodations. The nearest airport is Bradley International Airport, 38 mi from the property.

- "Love it!" - "Stayed overnight for a Tanglewood concert and had a great time" - "I do Highly recommend this place" - "Satisfied couple" - "Had a family funeral but it was nice to relax in the pool, use the gym and cook at home" - "Loved it" - "Perfect!" - "Great stay, would like to go back." - "Beautiful Villa" - "Great Value" - "Outstanding" - "A wonderful place to relax and enjoy all the amenities."

Located in Hancock with commanding views of the Jiminy Peak ski area, Vacation Village in the Berkshires offers endless recreational activities and many of the comforts of home. Lounge or swim in the indoor or outdoor pools. Go hiking, biking, or horseback riding around the resort. Enjoy a tranquil day, or take a soothing soak in the outdoor hot tub. A fitness center is available for our more active guests. Nearby you’ll find Mt. Greylock State Reservation, Pittsfield State Forest, and many opportunities to enjoy the arts; Hancock Shaker Museum, Tanglewood, Williamstown Theater, MASS MoCa and the Clark Institute and Museum!
Spacious One Bedroom (785 sq ft), sleeps 4. Beautifully furnished with integrated living and dining areas for entertaining and enjoyment. Partial Kitchen w/ refrigerator, microwave, toaster and coffee maker. Private balcony, CD/DVD players, TVs in bedroom and living room; with washer and dryer located on every floor.

- "Great spot" - "We enjoyed staying at this clean, quiet, and comfy property. Close to so many beautiful spots! Only minutes to both New York and Vermont!"

Nestled on Hancock, Massachusetts’ ski slopes, Jiminy Peak Mountain Resort offers a restaurant, adventure parks and ski-to-door access. It spacious suites and apartments feature a flat-screen TV and DVD player. Each suite features a sofa bed and fully equipped kitchenette. The one bedroom suites have 1 full bathroom, while the two and three-bedroom apartments feature a fully equipped kitchen and 2 bathrooms. Guests can swim in the outdoor pool or relax in the indoor hot tub. They can also workout in the gym or enjoy the tennis courts. The hotel offers a ski shop, ski lessons and ski storage. On-site dining is available at John Harvard's Restaurant (winter only) and Christiansen’s Tavern. - please call the Resort for hours of operation. Jiminy Peak Mountain Adventure Resort is within 8 miles of Balance Rock State Park and Pontoosuc Lake. It is 11 miles from Berkshire Museum. The resort is powered by 100 percent renewable energy. A wind turbine, solar field and co-generation facility all located on the western Massachusetts property makes the resort energy self-sufficient. Public areas are accessible from the front entrance including meeting spaces, restrooms, restaurants, and pool facilities.

- "Went for Thanksgiving and had dinner at John Harvard located on the 3rd floor of the county inn. Food was amazing as th" - "Brief but memorable" - "Excellent" - "very good" - "Amazing peaceful weekend" - "Nice resort a bit outdated" - "It was my birthday getaway we as a family and friends do one every year." - "Very good value.good Location." - "We had a great time staying at Country Inn!" - "Beautiful location and good value for summer."

Get ready for an unforgettable family escape at Wyndham Bentley Brook, where breathtaking natural beauty and year-round fun await! Nestled at the base of Jiminy Peak Ski Mountain, this two-bedroom suite provides the perfect retreat after a day of adventure, offering cozy comfort with a flat-screen TV, air conditioning, a kitchenette, and free Wi-Fi.

In the winter, Wyndham Bentley Brook is a skier’s paradise—step right outside your door and onto the lifts for seamless ski-in, ski-out access. When the snow melts, the fun continues! Explore the picturesque Berkshire Mountains with hiking, horseback riding, and outdoor concerts at nearby Tanglewood. As the seasons change, the vibrant fall foliage creates a spectacular backdrop for your outdoor adventures.

Beyond its stunning mountain setting, Wyndham Bentley Brook is the ideal home base for exploring Berkshire County’s rich cultural scene. Visit world-class museums, historic landmarks, charming shops, and restaurants that celebrate the region’s art and history. Whether you're hitting the slopes or discovering the natural and cultural wonders of the Berkshires, this resort is perfectly positioned for year-round excitement.

Why Wyndham Bentley Brook is a "Can't Miss" Destination:

- Ski-in, ski-out access at the base of Jiminy Peak Ski Mountain for the ultimate winter getaway.
- Year-round activities including hiking, horseback riding, and concerts at nearby Tanglewood.
- Close proximity to cultural attractions, museums, and historic landmarks in Berkshire County.
- Spacious two-bedroom suites with modern amenities, perfect for families and groups.

With the perfect blend of mountain adventure, scenic beauty, and cultural exploration, Wyndham Bentley Brook is your go-to destination for an unforgettable vacation in the heart of the Berkshires!

Items to note:
- The bed size in the second bedroom can vary.
-The resort will be undergoing renovations to multiple buildings from Apr. 30, 2025 through Sep. 15, 2025. During this time the Game room will be closed and detours to access to the pool will be required. You may experience noise, dust, odors and work crews. Dates are subject to change.
- Closest shopping/entertainment/additional dining: 30 minutes away
- Closest nightlife is in Albany, 45 minutes away
- Vehicle recommended to enjoy area
- A credit card is required for the $250 security deposit requested at check in.

KOALA Disclosure Summary:

-IMPORTANT: Payments appear as “KOALA VACATIONS” on credit card statements.

-BEFORE YOUR CHECK-IN: This booking requires the name and address of the person checking in. THE PERSON CHECKING IN MUST MATCH THE PHOTO ID PROVIDED TO US.

-The primary guest checking in must be at least 21 years old.

-Resorts own and manage all units/amenities; unit assignments at check-in.

-Room photos are samples; actual furniture/layout may vary.

-The Resort is responsible for maintenance, may alter/close select amenities due to COVID-19 or other factors. KOALA is only responsible for ensuring your check-in and unit category.

-KOALA is not responsible for unit condition or resort services. For resort, unit or guest related issues after check-in, please contact the resort management.

-Check cancellation policy before booking. No refunds after the cancellation deadline due to any reason, including COVID-19 (except full resort closures), natural disasters, or personal changes. For these reasons we always recommend purchasing trip insurance for unforeseen circumstances like these.

This resort is part of a timeshare and you may be invited to attend a sales presentation. Any participation is always optional and never required when booking through KOALA.

Security/Safety • Hot Tub • Spa • Laundry • Tv • Entertainment • Internet • Balcony/Terrace • Bedding/Linens • Wellness Facilities • Pool • Barbecue/Outdoor Cooking

Cozy Great Barrington Home about 1 Mi to Ski Resort! is located in Great Barrington, just 14 miles from Cranwell Spa & Golf Club and 14 miles from Tanglewood Musical Center. This vacation home provides accommodations with a patio. Free Wifi is available throughout the property and Norman Rockwell Museum is 11 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. For added privacy, the accommodation features a private entrance. Tanglewood is 14 miles from the vacation home, while Great Falls is 16 miles away. Bradley International Airport is 43 miles from the property.

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

Get ready for an unforgettable family escape at Wyndham Bentley Brook, where breathtaking natural beauty and year-round fun await! Nestled at the base of Jiminy Peak Ski Mountain, this two-bedroom suite provides the perfect retreat after a day of adventure, offering cozy comfort with a flat-screen TV, air conditioning, a kitchenette, and free Wi-Fi.

In the winter, Wyndham Bentley Brook is a skier’s paradise—step right outside your door and onto the lifts for seamless ski-in, ski-out access. When the snow melts, the fun continues! Explore the picturesque Berkshire Mountains with hiking, horseback riding, and outdoor concerts at nearby Tanglewood. As the seasons change, the vibrant fall foliage creates a spectacular backdrop for your outdoor adventures.

Beyond its stunning mountain setting, Wyndham Bentley Brook is the ideal home base for exploring Berkshire County’s rich cultural scene. Visit world-class museums, historic landmarks, charming shops, and restaurants that celebrate the region’s art and history. Whether you're hitting the slopes or discovering the natural and cultural wonders of the Berkshires, this resort is perfectly positioned for year-round excitement.

Why Wyndham Bentley Brook is a "Can't Miss" Destination:

- Ski-in, ski-out access at the base of Jiminy Peak Ski Mountain for the ultimate winter getaway.
- Year-round activities including hiking, horseback riding, and concerts at nearby Tanglewood.
- Close proximity to cultural attractions, museums, and historic landmarks in Berkshire County.
- Spacious two-bedroom suites with modern amenities, perfect for families and groups.

With the perfect blend of mountain adventure, scenic beauty, and cultural exploration, Wyndham Bentley Brook is your go-to destination for an unforgettable vacation in the heart of the Berkshires!

Items to note:
- The bed size in the second bedroom can vary.
-The resort will be undergoing renovations to multiple buildings from Apr. 30, 2025 through Sep. 15, 2025. During this time the Game room will be closed and detours to access to the pool will be required. You may experience noise, dust, odors and work crews. Dates are subject to change.
- Closest shopping/entertainment/additional dining: 30 minutes away
- Closest nightlife is in Albany, 45 minutes away
- Vehicle recommended to enjoy area
- A credit card is required for the $250 security deposit requested at check in.

KOALA Disclosure Summary:

-IMPORTANT: Payments appear as “KOALA VACATIONS” on credit card statements.

-BEFORE YOUR CHECK-IN: This booking requires the name and address of the person checking in. THE PERSON CHECKING IN MUST MATCH THE PHOTO ID PROVIDED TO US.

-The primary guest checking in must be at least 21 years old.

-Resorts own and manage all units/amenities; unit assignments at check-in.

-Room photos are samples; actual furniture/layout may vary.

-The Resort is responsible for maintenance, may alter/close select amenities due to COVID-19 or other factors. KOALA is only responsible for ensuring your check-in and unit category.

-KOALA is not responsible for unit condition or resort services. For resort, unit or guest related issues after check-in, please contact the resort management.

-Check cancellation policy before booking. No refunds after the cancellation deadline due to any reason, including COVID-19 (except full resort closures), natural disasters, or personal changes. For these reasons we always recommend purchasing trip insurance for unforeseen circumstances like these.

This resort is part of a timeshare and you may be invited to attend a sales presentation. Any participation is always optional and never required when booking through KOALA.

Bedding/Linens • Fireplace/Heating • Internet • Entertainment • Tv • Hot Tub • Wellness Facilities • Security/Safety • Barbecue/Outdoor Cooking • Laundry • Balcony/Terrace • Air Conditioner

Walk to Ski Slopes Jiminy Peak Resort Getaway! is located in Hancock, just 21 miles from Cranwell Spa & Golf Club and 21 miles from Tanglewood Musical Center. This apartment offers air-conditioned accommodations with a balcony and free Wifi. The apartment has an outdoor pool and a hot tub. The apartment features 3 bedrooms, a fully equipped kitchen with a dishwasher and an oven, a washing machine, and 3 bathrooms with free toiletries. Towels and bed linen are offered in the apartment. The property has an outdoor dining area. Tanglewood is 21 miles from Walk to Ski Slopes Jiminy Peak Resort Getaway!, while Norman Rockwell Museum is 27 miles from the property. Albany International Airport is 35 miles away.

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

Your cozy getaway awaits in Lee at this delightful Oak n'Spruce Resort. With 2 bedrooms, including a king bed and a queen bed, this property is perfect for a small group of guests. The resort offers excellent amenities such as an iron, fitness room, WiFi, hair dryer, heating, coin laundry, and AC. The 2 bathrooms are equipped with a jetted bathtub and a hair dryer. Additionally, there is an additional space with a living room and a sofa bed. We hope you'll enjoy your stay at our marvelous resort.

Air Conditioner • Other • Security/Safety • Laundry • Child Friendly • Hot Tub • Internet • Bedding/Linens • Fireplace/Heating • Wellness Facilities

Cozy Ski in out Cabin in Berkshire Resort is a recently renovated vacation home in Hancock where guests can make the most of the fitness center and garden. This vacation home offers air-conditioned accommodations with a patio. There's a year-round outdoor pool and guests have access to free Wifi, free private parking, and an electric vehicle charging station. Offering a terrace and mountain views, the spacious vacation home includes 2 bedrooms, a living room, flat-screen TV, an equipped kitchen, and 2 bathrooms with a hot tub and a bath. Towels and bed linen are featured in the vacation home. The property has an outdoor dining area. A mini-market is available at the vacation home. A ski equipment rental service, ski-to-door access, and a ski pass sales point are all offered at the vacation home, and guests can go skiing in the surrounding area. Cranwell Spa & Golf Club is 20 miles from Cozy Ski in out Cabin in Berkshire Resort, while Tanglewood Musical Center is 21 miles from the property. Albany International Airport is 34 miles away.

- "Cozy, warm, and perfect location."

* Cozy Ski-In/Ski-Out Cabin at Jiminy Peak – Perfect for Couples, Friends & Families

Escape to the heart of the Berkshires at our charming single-level cabin nestled within the Jiminy Peak Ski Resort. Whether it’s a romantic retreat, a fun trip with friends, or a family vacation, our home is the perfect base to explore everything the region has to offer—from outdoor adventures, hiking, and lake swimming to mountain rides and world-class arts, music, and cultural events.

* The Cabin

Location: Country Village section of Jiminy Peak, 4th house in the row, large grassy area, plenty of parking.

Layout: Single-level with 2 bedrooms and 1.5 baths.

Master Bedroom: Queen bed, closet, dresser, lamps, TV + DVD player

Second Bedroom: Queen bed + twin trundle, small closet, dresser, lamp

Living Room: Pull-out double sofa bed, smart TV, coffee table, lamps, extra seating

Comfort: Cozy furnishings and all essentials for a relaxing stay

* Resort Amenities & Activities

Ski-In/Ski-Out Access on Jiminy Peak slopes

Mountain Rides: Memorial Day Weekend through end of September

Pools & Jacuzzi:

Outdoor heated pool at the Country Inn (open year-round when temps are above 25°F)

Seasonal outdoor pool in the Country Village section, a few minutes’ walk from the cabin

Heated indoor jacuzzi + outdoor jacuzzi at the Country Inn building

Fitness & Sports: Small gym in the Country Inn building, outdoor tennis court

Convenience: 5-minute walk to main Country Inn building and store (7–7 or 8–8 depending on day)

Nearby Golf: Driving range and 9-hole course at resort entrance (not included in guest access)

* Explore the Berkshires

Arts & Culture: Mass MoCA (30 min), Tanglewood (35 min), Clark Art Institute (35 min), Norman Rockwell Museum (40 min), Berkshire Museum (25 min)

Local Farms & Spa: Hilltop Orchard & Winery, Loka Valley Farm, Miraval Spa

Horseback Riding:

Cinch 'em Up Stables – 15 min

Undermountain Farm – 25 min

Berkshire HorseWorks – 40 min

Aisling Mountain Farm – 30 min

* Local Dining Favorites

Bluebird & Co. – Global cuisine, lawn games, live music, short walk from cabin

John Harvard’s Restaurant & Brewery – American fare, onsite at Country Inn, mountain views

Norte Azul Cantina – Mexican, Stephentown, NY (10 min drive)

Alta – Mediterranean, Lenox (20 min drive)

Crust Pizza & Ayelada Frozen Yogurt – Pittsfield

The Red Lion Inn – Historic American cuisine, Stockbridge

Mezze Bistro + Bar – Mediterranean, Williamstown

Gateways Dine & Drink – Farm-to-table, Lenox

The Barn Kitchen & Bar – New England classics, Williamstown

STATE Food + Drink – West Coast flavors with Berkshire ingredients, North Adams

Chatham Brewing – Brewery & pub fare, Chatham, NY

Bright Ideas Brewing – Craft beers at Mass MoCA, North Adams

* Swimming & Fishing Lakes

Pontoosuc Lake – 14 min

Margaret Lindley Park – 15 min

Burbank Park (Pittsfield) – 19 min

Plunkett Reservoir (Hinsdale) – 30 min

Sandy Beach at Laurel Lake (Lee) – 39 min

Lake Mansfield (Great Barrington) – 47 min

* Hiking Trails

On-Site: Hike Jiminy Mountain from your doorstep

Shaker Trail (Pittsfield) – 19 min

Pittsfield State Forest – 23 min

Mauserts Pond Trail – 46 min

- "This property was great. It is close to the ski trails, and fun. We hope to stay here again." - "We were attending 2 shows at Tanglewood during our stay and it was convenient for our other activities also." - "We squeezed a lot into a short weekend—rode the alpine slides and mountain coaster Friday evening, enjoyed tossing a disc in the grassy back yard, hiked Mt Greylock Saturday morning and hopped over to Tanglewood for dinner and a concert that evening. Nice location, comfortable space."

Experience Leisure - Resort Condos in the Berkshire Hills is set in South Lee. The accommodation has a sauna. There is a fully equipped kitchen and a private bathroom. Hudson is 43 km from the apartment, while Pittsfield is 20 km from the property. The nearest airport is Bradley International, 61 km from Experience Leisure - Resort Condos in the Berkshire Hills, and the property offers a free airport shuttle service.

Hot Tub • Laundry • Private Pool • Pool

Stay at the heart of it all. Walk to lifts, restaurants, shopping and amenities right from your door. It doesn’t get any easier than staying at JJ Lodge at the Village Center at Jiminy Peak. Views of mountain and Cricket Chair to start your day on the snow. Private Jacuzzi tub to soak tired ski legs and chase away the chill at the end of the day.. Stay cozy in front of the fire place. Create intimate experiences in any room with Lutron's smart dimmers and lighting. Sleep soundly on the Queen bed. Power on the towel warmer for a warm, spa-like welcome out of the shower. Stay connected with Wi-Fi. Private gated parking. Note: Up to two additional guests may sleep in living area, at no additional fee, on twin inflatable beds, provided.

- "My wife and I spent a long weekend at this location. Clean, comfortable and quiet. Great central location for many spots in the upper Berkshire area. Pool was terrific!" - "The property was in the perfect location and the owners were very responsive to all inquiries." - "Great place to stay very clean and comfortable." - "Great place to stay. Easy access to the mountain and great layout for our family." - "Great time at jiminy! This unit was super clean and super convenient to everything at jiminy including the lodge and lifts! Thank you for the speedy communication! Appreciate it! We’ll be back next year! Thanks!"

Set amid a mountain haven, Bentley Brook Ski Oasis delivers an unmatched winter sanctuary. With seamless ski access, this enclave embodies opulence, blending elite services, lavish amenities, and awe-inspiring alpine panoramas for an unparalleled escape. Whether you crave the exhilaration of the slopes or aspire to refined comfort, Bentley Brook Ski Oasis ensures a distinctive alpine retreat.

- "Great as always " - "Responsive and informative host. Great location ski out. " - "Great location, clean and perfect for a family! " - "Easy booking, great ski weekend. Very positive experience!" - "We enjoyed the condo. Has everything that we needed and we were able to walk to the mountain in 5 minutes. Clean condo and clean white bedding. Plenty of towels and pool towels. " - "Great spot. We had a ton of fun."

Set amid a mountain haven, Bentley Brook Ski Oasis delivers an unmatched winter sanctuary. With seamless ski access, this enclave embodies opulence, blending elite services, lavish amenities, and awe-inspiring alpine panoramas for an unparalleled escape. Whether you crave the exhilaration of the slopes or aspire to refined comfort, Bentley Brook Ski Oasis ensures a distinctive alpine retreat.

- "Jimney is always a great time" - "These units are convenient, clean and spacious.We had the two bedroom/two bathroom & it was perfect for our family. So close to the mountain and restaurants too. " - "Na" - "Very easy access to the slope and perfect for family with kids"

Bentley Brook Resort stands as a winter haven, providing unmatched ski-in, ski-out grandeur. Immerse yourself in the enchantment of the snow-clad landscape, enjoying top-notch amenities, snug alpine lodgings, and invigorating outdoor escapades. Whether you're a seasoned snow aficionado or seeking a tranquil mountain refuge, our resort assures an extraordinary blend of excitement and repose. Unwind in style, embrace the crisp mountain zephyr, and craft unforgettable moments amid the breathtaking allure of Bentley Brook. Your premier ski resort sojourn awaits, where each moment unfolds as a tribute to the enchanting magic of winter allure.

- "My family had a blast here and appreciate the availability. The property is situated perfectly for skiing on/off of Jiminy Cricket. Ski lockers made it even easier. We loved the spacious rooms, whirlpool bath, laundry and kitchen. My son said he wanted to move in :) Towels for bath and pool, coffee & filters, and laundry detergent provided. Free wifi and plenty of activities if you aren't skiing or apres-ski. There are 2 EV charging stations at one of the buildings and front desk avail 24/7. "

Ski-in and Ski-out your front door! Bentley Brook is situated right at the base of Jiminy Peak Ski Mountain, making this resort an exceptional choice for mountainside play. In winter, ski out your door and onto the lifts; in spring, summer and fall, enjoy hiking, horseback riding, Tanglewood concerts and brilliant foliage. The area delivers a wealth of cultural attractions, museums, historic landmarks, shops and restaurants, making Wyndham Bentley Brook the perfect home base for exploring nearby Berkshire County towns and attractions.

These spacious studio, one- and two-bedroom resort suites comfortably sleep four to eight guests and range from 400 to 953 square feet. Suites feature one queen bed and one double sleeper sofa in the studio, two queen beds and a queen sleeper sofa in the one-bedroom and one king bed with varying bedding for the guest room with a queen sleeper sofa in the living area for the two-bedroom resort suite. You will appreciate the privacy of separate bedrooms, a full kitchen, dining areas and free Wi-Fi throughout. Upgrade to a one-bedroom for a private balcony, or a two-bedroom for a washer/dryer - all comforts that would be hard to find in an average hotel.

- "We just spent a couple nights here but enjoyed our time here. There was plenty of room for 4 people and it was a close walk to the base of Jiminy Peak for the adventure park. Staff was helpful and friendly as well. "

Bentley Brook Resort offers an unparalleled getaway at the base of Jiminy Peak. Nestled in the picturesque Berkshires, this premier retreat w/ luxury accommodations with access to world-class skiing.

- "This property is great for skiing, especially with kids. There is a nice pool and little movie theater thats prefect for after a day on the slopes." - "This resort is ski in ski out . You can’t beat that . The rooms are specious and kitchen and living room are add space. Everything is right there . Pool and hot tubs are great after skiing. We love Bentley Brook has been coming here for 8 years " - "Everything was great."

Whether you're a seasoned skier or a first-time adventurer, our resort caters to all, providing access to pristine slopes for a range of skill levels. After a day of conquering the mountains, retreat to our inviting spaces where warmth and comfort await.

Indulge in exquisite dining at our on-site restaurants, savoring culinary delights that complement the alpine ambiance. Our commitment to excellence extends beyond the slopes, ensuring your entire stay is a memorable journey filled with relaxation, adventure, and unparalleled luxury.

Escape to Bentley Brook Ski-In/Ski-Out Resort, where the allure of the mountains meets the sophistication of a world-class resort. Your alpine retreat awaits, promising an unforgettable blend of excitement and serenity. ⛷️🏔️✨ #BentleyBrook #SkiInSkiOut #AlpineLuxury #MountainRetreat"

- "The property manager was great and very communicative. The hotel is the perfect place to stay if skiing at Jiminy peak. Ski school right outside, pool and arcade room for the children." - "This condo was perfect for our family. We had lots of space and we were right on the base of Jiminy peak. I would definitely stay again."

Welcome to the enchanting world of Wyndham Bentley Brook, an exclusive ski-in/ski-out retreat cradled in the breathtaking Berkshires! Immerse yourself in the pinnacle of winter luxury, where serenity dances with adrenaline. Our resort unveils sumptuous accommodations, each a haven of comfort, seamlessly connecting you to the slopes for a day of boundless adventure.

Discover the allure of generously appointed suites, meticulously crafted to cocoon you in warmth after an exhilarating day on skis or a snowboard. Indulge in the resort's opulent amenities, including rejuvenating indoor and outdoor pools, therapeutic hot tubs, and a cutting-edge fitness center that beckons the active spirit. Delight your palate with culinary delights at our on-site dining options or embark on a gastronomic journey through the vibrant local scene.

- "Fun time. Conditions were good. We love this family Mountain " - "Great place to get my 6 year old on the mountain. What a great time !"

Ski-in and Ski-out your front door! Bentley Brook is situated right at the base of Jiminy Peak Ski Mountain, making this resort an exceptional choice for mountainside play. In winter, ski out your door and onto the lifts; in spring, summer and fall, enjoy hiking, horseback riding, Tanglewood concerts and brilliant foliage. The area delivers a wealth of cultural attractions, museums, historic landmarks, shops and restaurants, making Wyndham Bentley Brook the perfect home base for exploring nearby Berkshire County towns and attractions.

These spacious studio, one- and two-bedroom resort suites comfortably sleep four to eight guests and range from 400 to 953 square feet. Suites feature one queen bed and one double sleeper sofa in the studio, two queen beds and a queen sleeper sofa in the one-bedroom and one king bed with varying bedding for the guest room with a queen sleeper sofa in the living area for the two-bedroom resort suite. You will appreciate the privacy of separate bedrooms, a full kitchen, dining areas and free Wi-Fi throughout. Upgrade to a one-bedroom for a private balcony, or a two-bedroom for a washer/dryer - all comforts that would be hard to find in an average hotel.

Air Conditioner • Kitchen • Balcony/Terrace • Security/Safety • Skiing • Spa • Parking • Guest Services • Accessibility • Laundry • Other • Wellness Facilities

Complete your Berkshires retreat with a stay in the spacious Studios, perfect for romantic couples and small families. Suites feature plush bedding, additional sleeper sofa and fully equipped kitchen for all your dining needs.

* Minimum age to check in is 21
* Daily housekeeping is not included and may be added for a nominal fee
* Please note that images are representative and units may vary slightly

- "Did not clearly identify the layout of a studio. Also, there was no hot water and the flow was poor. They did fix temp but too late for me to shower before needing to leave for a wake/funeral. "

The Berkshire Mountain Lodge features one-bedroom condominiums equipped with modern amenities such as full kitchens and cozy living and dining areas. The Berkshires is a cultural art haven that is home to attractions like American author Edith Wharton’s self-designed estate, The Mount and Tanglewood, the summer home of the Boston Symphony. Located near Lenox, Mass Berkshire Mountain Lodge is a family vacation destination for all seasons that will include days filled with countryside beauty, and an abundance of activities that stimulate the senses and energize the body. During the summer and spring visit the area’s many museums, theaters, concert halls, and historic homes. The county’s lakes and rivers are perfect for boating, kayaking, swimming, and fishing. Take advantage of the miles of country lanes for hiking and biking, enjoy a round of golf or go zip-lining with the kids on a nearby mountain. Many places pale in comparison to the Berkshires fall foliage season. A refuge of natural beauty; experience nature’s kaleidoscope of colors in cooler weather while you peruse though numerous outdoor bazaars and markets.

- "We loved everything about this place! It was quiet, centrally located, and everyone was friendly and helpful. We will stay here again for sure!"

Embark on an Alpine Odyssey at Bentley Brook Ski-In/Ski-Out Resort, a haven for both seasoned skiers and first-time adventurers alike. Our resort is tailored to cater to a spectrum of skill levels, ensuring everyone finds their perfect slope. After a day of conquering the mountains, escape to our inviting spaces where warmth and comfort await, creating an atmosphere of pure relaxation.

Savor the culinary delights of our restaurants within walking distance, where exquisite dining experiences complement the enchanting alpine ambiance. At Bentley Brook, our commitment to excellence transcends the slopes, curating an entire stay filled with moments of adventure, relaxation, and unparalleled luxury.

- "Walked out of the building, straight into my kids skiing lessons, very convenient."

A stay at Bentley Brook Resort is a cozy, mountain retreat. Enjoy ski-in, ski-out access, spacious accommodations, and on-site amenities, creating a perfect blend of relaxation and adventure. Whether you're hitting the slopes or exploring the Berkshires, it's a memorable experience in every season.

- "Great property! Great location. Smooth check-in."

At the base of Jiminy Peak Ski Mountain, an exceptional choice for mountainside play with access to ski lifts and equipment rental just a few feet away, a winter wonderland for all ages. The area delivers a wealth of adventure making this the perfect home base for exploring Berkshire County attractions; mountainside rollercoasters and ropes courses to play on during the summer months there’s always something to do. After a day at play come back and enjoy one of the hot tubs or relax by the pool.

- "Large property with ski-in/ski-out proximity to Jiminy Peak. Units are standard but large, clean, and with helpful amenities for a family vacation (kitchenette in unit, plus nice pool for kids' apres-ski, kids' movies, etc.) We'll be back."

At the base of Jiminy Peak Ski Mountain, an exceptional choice for mountainside play with access to ski lifts and equipment rental just a few feet away, a winter wonderland for all ages. The area delivers a wealth of adventure making this the perfect home base for exploring Berkshire County attractions; mountainside rollercoasters and ropes courses to play on during the summer months there’s always something to do. After a day at play come back and enjoy one of the hot tubs or relax by the pool.

- "We really enjoyed our stay and it was nice to be so close to the slopes."

Welcome to Wyndham Bentley Brook, your gateway to the ultimate ski-in, ski-out experience at the majestic Jiminy Peak! Nestled in the heart of the picturesque Berkshire Mountains, this resort is a winter wonderland for snow enthusiasts and adventure seekers alike.

Discover the epitome of convenience as you step right outside your door onto the pristine slopes of Jiminy Peak. Wyndham Bentley Brook offers unparalleled access to world-class skiing and snowboarding, ensuring that every moment on the mountain is filled with exhilaration and joy.

The resort itself is a haven of comfort and luxury, featuring well-appointed accommodations designed to provide a cozy retreat after a day of thrilling outdoor activities. Spacious suites equipped with modern amenities offer a warm and inviting atmosphere, allowing you to unwind and recharge for another day of alpine adventures.

Other • Air Conditioner • Child Friendly • Laundry • Parking • Internet • Tv • Kitchen • Pool • Accessibility • Security/Safety • Wellness Facilities

Experience the ultimate ski-in, ski-out getaway at Wyndham Bentley Brook, nestled in the heart of the Berkshire Mountains. Enjoy unparalleled access to Jiminy Peak's pristine slopes, luxurious accommodations, and a cozy retreat after exhilarating outdoor adventures. Your winter wonderland awaits!

Kitchen • Pool • Laundry • Child Friendly • Wellness Facilities • Air Conditioner • Entertainment • Bedding/Linens • Hot Tub • Parking • Sports/Activities • Internet

At the base of Jiminy Peak Ski Mountain, an exceptional choice for mountainside play with access to ski lifts and equipment rental just a few feet away, a winter wonderland for all ages. The area delivers a wealth of adventure making this the perfect home base for exploring Berkshire County attractions; mountainside rollercoasters and ropes courses to play on during the summer months there’s always something to do. After a day at play come back and enjoy one of the hot tubs or relax by the pool.

Internet • Fireplace/Heating • Bedding/Linens • Kitchen • Other • Hot Tub • Accessibility • Tv • Pool • Skiing • Security/Safety • Laundry

This is a 3 bedroom business listing for Jiminy Peak located in Country Village condo area about a 1/4-1/2 mile off the base of the mountain. All units are all privately owned and we are the management company that rents these units in the owners interest.

The pictures you see are a collection of our different units that we rent. The floor plan of each condo is the same, it will just be different décor and furnishings. If you want something specific you will need to call the property directly.

The space
Nestled in the Berkshires, a getaway to Jiminy Peak offers everything you need, so close to home. Spend less time traveling and more time on the slopes during the winter or enjoying the thrills and challenges of Mountain Adventure in the summer season. When your day is done, take a short walk back to your room or vacation home to relax before heading to dinner at one of our on site restaurants. Jiminy offers all that you need in a resort experience – lodging, dining, shopping and an array of activities and entertainment.

Guest access
Please check in at the Front Desk of the Country Inn. 37 Corey Rd. Hancock, MA Check in time is 4pm.

Other things to note
You must be 21 years of age or older with valid proof of ID, and credit card.

Body soap • Hot water • Free washer – In unit • Hair dryer • Shampoo • Essentials • Shower gel • Bathtub • Conditioner • Free dryer – In unit

These are our 2 bedroom business listings for Jiminy Peak located in our Country Village and Mountainside condo area about a 1/4-1/2 mile off the base of the mountain. All units are all privately owned and we are the management company that rents these units in the owners interest.

The pictures you see are a collection of our different units that we rent. If you want something specific you will need to call the property directly.

The space
We provide all linens, silverware, dishes, and pans for the unit.

Guest access
Please check in at the Front Desk of the Country Inn. 37 Corey Rd. Hancock, MA. Check in time is 4pm.

Other things to note
You must be 21 years of age or older with valid proof of ID, and credit card.

Hangers • TV with standard cable • Essentials • Shampoo • Hair dryer • Iron • Air conditioning • Bathtub • Washer • Dryer

Club Wyndham Bentley Brook is situated right at the base of Jiminy Peak Ski Mountain, making this resort an exceptional choice for mountainside play. Ski or snowboard down the well-groomed trails of Jiminy Peak, enjoy hiking, tennis and mountain biking, or swimming at the on-site pools. This studio suite offers one queen Murphy bed and one queen sleeper sofa. Additional amenities include a full kitchen and dining area.

The space
This spacious studio suite measures approximately 400 square feet. You will enjoy one queen Murphy bed and one queen sleeper sofa. Additional amenities include a full kitchen and dining area. Maximum occupancy is four.

Guest access
Resort Amenities:
• Activities Center
• Activities Desk
• Arcade Games
• Barbecue Area
• Casual Dining
• Computer With Internet (Shared)
• Concierge Services
• Convenience Store
• Fitness Center
• Game Room
• Hot Tub (Indoor)
• Hot Tub (Outdoor)
• Laundry Facilities (Coin-Operated)
• Locker Rooms
• Massage Services
• Movie Rentals
• Owner Lounge
• Picnic Area
• Sauna
• Ski Lift
• Ski/Mountain Bike Storage
• Sunbathing Area
• Swimming Pool (Adult)
• Swimming Pool (Indoor/Outdoor)
• Tennis Court
• Wi-Fi Internet Access

RENOVATION: The resort will be undergoing renovations to multiple buildings from Apr. 30, 2025 through Sep. 15, 2025. During this time the Game room will be closed and detours to access to the pool will be required. You may experience noise, dust, odors and work crews. Dates are subject to change.

FEE: Wifi available on property with an associated fee determined by the property. Additional fees will be collected on arrival per guest request.

Closest shopping/entertainment/additional dining: 30 minutes away.

Closest nightlife is in Albany, 45 minutes away.

Vehicle recommended to enjoy area.

Other things to note
A valid government-issued identification and major credit card matching the name of the primary guest on the reservation is required at check-in.

You must be at least 21 years of age to check in and register for a room.

If reservation guest name needs to be changed, please contact via Airbnb message board or call Extra Holidays at phone:800-917-1591.

A $250 security deposit (per stay) in addition to any remaining balance is due at the time of check-in. The security deposit will be released upon check-out and can take up to 7-14 business days to reflect in your account.

The resort accepts Visa, Mastercard, American Express, and Discover credit cards. Pre-paid cards, checks and credit card authorization forms are not accepted.

Unless specified in the listing description, room views and bedding configurations are not guaranteed and based on availability at check-In. Room décor and floor plans may vary slightly.

Conditioner • Body soap • Shampoo • Bed linens • Hair dryer • Essentials • Iron • Extra pillows and blankets • TV with standard cable • Exercise equipment