Berkshire Area Rentals
From $471 per night (USD)VRBO
Pet Friendly Oasis on 5 Private Acres, 10 min to Tanglewood
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
Escape to this peaceful retreat on 5 private acres. Large picture windows envelope you in the gorgeous surroundings, and ...
From $471 per night (USD)VRBO
From $645 per night (USD)Expedia
Spacious 4BR Central-Berkshires Home with POOL!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Spacious and comfortable home in a serene setting and ideal location. Whether you are coming for performing arts, museu ...
From $645 per night (USD)Expedia
From $564 per night (USD)VRBO
Available February 17-21 2025. Sleep 8 - 2-bed apt on Jiminy Peak. Ski in\/out!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Available February 17-21 - President’s week 2025! Condo Resort at Jiminy Peak Ski Mountain's Base Enjoy ski retreat at ...
From $564 per night (USD)VRBO
From $291 per night (USD)Expedia
Golf, Swim & Ski: Gem w\/ Lake Access in Pittsfield
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
4 Seasons of Fun | Near Outdoor Activities | Movie Nights at Home Get back to nature at this 2-bedroom, 2-bath Pittsfie ...
From $291 per night (USD)Expedia
From $177 per night (USD)VRBO
Charming Lakeview Cottage in Heart of the Berkshires
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
Relax in your island cottage overlooking beautiful Onota Lake in the heart of the Berkshires. Take in 180 degree pristin ...
From $177 per night (USD)VRBO
From $346 per night (USD)VRBO
Monterey, MA. Near Tanglewood, Charming rustic farm house, well equipped kitchen
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 7
Air conditioned. Situated on 11 acres, totally private, surrounded by apple orchard, open fields and bordering woods. N ...
From $346 per night (USD)VRBO
From $673 per night (USD)VRBO
Condo Resort at Jiminy Peak Ski Mountain's Base
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Enjoy great year round activities from white water rafting and hiking in the summer, to skiing at the famous Jiminy Peak ...
From $673 per night (USD)VRBO
From $224 per night (USD)VRBO
Zen Riverfront studio w\/ Spa steam shower, wood stove, SKI Catamount \/Butternut
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Tucked away in Great Barrington, this marvelous, newly renovated, sunny studio features a well equipped kitchenette, a c ...
From $224 per night (USD)VRBO
From $369 per night (USD)VRBO
Cozy Condo Near MASS MoCA
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Your Modern Bohemian Retreat in North Adams Experience a blend of contemporary comfort and bohemian charm in ...
From $369 per night (USD)VRBO
From $475 per night (USD)VRBO
Steepletop: Nature Lover’s Paradise w\/Rec Room
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Welcome to Steepletop Lodge, a beautiful 4 bed/ 2 bath modern retreat with endless opportunities to unplug and ...
From $475 per night (USD)VRBO
From $536 per night (USD)VRBO
Chalet des Collines: 5 Mins to Catamount
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Gorgeous country escape set on 2 pastoral acres of a lovely meadow in the Taconic Range. Enjoy mountain biking ...
From $536 per night (USD)VRBO
From $545 per night (USD)VRBO
River Cottage: Riverfront Home, Walkable Community
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Welcome to River Cottage, a beautifully renovated 3-bedroom, 2-bathroom riverfront gem in the heart of Great Ba ...
From $545 per night (USD)VRBO
From $359 per night (USD)VRBO
Meadow Top Cottage: Countryside Cottage on 72 Acres
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Summary: Meadow Top Cottage is charming and cozy 3-bed, 2-bath cottage in the quiet hamlet of Mill River, MA. The 72-acr ...
From $359 per night (USD)VRBO
From $318 per night (USD)VRBO
All Season Adventures, Ski In\/Ski Out, Wyndham Bentley Brook 2 Bedroom Dlx.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Get ready for an unforgettable family escape at Wyndham Bentley Brook, where breathtaking natural beauty and year-round ...
From $318 per night (USD)VRBO
From $460 per night (USD)VRBO
Charming 3-bedroom in-town house with AC and WiFi in tranquil West Stockbridge
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This light filled; in-town home is a short walk to the picturesque Village of West Stockbridge. In town you'll find anti ...
From $460 per night (USD)VRBO
From $400 per night (USD)VRBO
Cozy Comfortable Three Bedroom Home in charming Williamstown
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Your Williamstown adventure begins at this 3-bedroom house. Each bedroom features a cozy king, queen, or full bed, ensur ...
From $400 per night (USD)VRBO
From $322 per night (USD)VRBO
All Season Adventures, Ski In\/Ski Out, Wyndham Bentley Brook 2 Bedroom Dlx.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Get ready for an unforgettable family escape at Wyndham Bentley Brook, where breathtaking natural beauty and year-round ...
From $322 per night (USD)VRBO
From $256 per night (USD)VRBO
Cozy 2-bedroom apartment with AC, fitness room and WiFi in welcoming Lee
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
After a day of mountain adventures, our Resort in the Berkshires is the perfect New England-y place to unwind and kick o ...
From $256 per night (USD)VRBO
From $256 per night (USD)VRBO
Cozy 2-bedroom apartment with WiFi, fitness room in enjoyable Lee
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
After a day of mountain adventures, our Resort in the Berkshires is the perfect New England-y place to unwind and kick o ...
From $256 per night (USD)VRBO
From $256 per night (USD)VRBO
Charming 2-bedroom apartment in Lee with fitness room, WiFi
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
After a day of mountain adventures, our Resort in the Berkshires is the perfect New England-y place to unwind and kick o ...
From $256 per night (USD)VRBO
From $261 per night (USD)VRBO
Cozy 2-bedroom apartment with WiFi, AC in welcoming Lee
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
After a day of mountain adventures, our Resort in the Berkshires is the perfect New England-y place to unwind and kick o ...
From $261 per night (USD)VRBO
From $256 per night (USD)VRBO
Cozy 2-bedroom apartment with fitness room, WiFi in fabulous Lee
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
After a day of mountain adventures, our Resort in the Berkshires is the perfect New England-y place to unwind and kick o ...
From $256 per night (USD)VRBO
From $367 per night (USD)VRBO
3 Bedroom home w\/ lake and mountain views near skiing, and cultural attractions!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Conveniently located near a lake, off of Route 7 on the way to attractions in both North Berkshire County and Southern B ...
From $367 per night (USD)VRBO
From $108 per night (USD)VRBO
1br Deluxe Condo Jiminy Peak Skiing!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Summary: This resort at the base of Jiminy Peak Ski Mountain is an excellent choice for mountainside recreation. It prov ...
From $108 per night (USD)VRBO
From $139 per night (USD)VRBO
2br DX Condo Ski & Berkshire County!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: This resort at the base of Jiminy Peak Ski Mountain is an excellent choice for mountainside recreation. It prov ...
From $139 per night (USD)VRBO
From $110 per night (USD)VRBO
1br Deluxe Condo Jiminy Peak Skiing!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Summary: This resort at the base of Jiminy Peak Ski Mountain is an excellent choice for mountainside recreation. It prov ...
From $110 per night (USD)VRBO
From $110 per night (USD)VRBO
1br Deluxe Condo Jiminy Peak Skiing!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Summary: This resort at the base of Jiminy Peak Ski Mountain is an excellent choice for mountainside recreation. It prov ...
From $110 per night (USD)VRBO
From $108 per night (USD)VRBO
1br Deluxe Condo Jiminy Peak Skiing!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Summary: This resort at the base of Jiminy Peak Ski Mountain is an excellent choice for mountainside recreation. It prov ...
From $108 per night (USD)VRBO
From $110 per night (USD)VRBO
1br Deluxe Condo Jiminy Peak Skiing!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Summary: This resort at the base of Jiminy Peak Ski Mountain is an excellent choice for mountainside recreation. It prov ...
From $110 per night (USD)VRBO
From $1077 per night (USD)VRBO
Large, comfortable house and yard located on a beautiful lake.
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 16
Bring extended family or a group of friends to this great house with lots of room for fun, on a beautiful lake, just min ...
From $1077 per night (USD)VRBO
From $528 per night (USD)VRBO
Tanglewood Chalet - Majestic View of Mountains \nMinutes to Tanglewood & Theaters
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 7
Beautiful, newly renovated home, surrounded by nature and very close to hiking trails and cultural and historical sites ...
From $528 per night (USD)VRBO
From $172 per night (USD)VRBO
In-law studio in the heart of the Berkshires!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
In-law studio in a super location in the heart of the Berkshires. Fully furnished and equiped, this sweet private-entra ...
From $172 per night (USD)VRBO
From $880 per night (USD)VRBO
2 Bedroom Deluxe Condo w\/ Full Kitchen at Bentley Brook, Jiminy Peak Ski Mount!!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
This spacious two-bedroom resort suite measures approximately 843 to 953 square feet. You will enjoy a king bed in the m ...
From $880 per night (USD)VRBO
From $191 per night (USD)Expedia
Berkshire Ashmere Lake lodging. Quiet room, Fantastic sunsets.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Bedroom with large master bath. Lockoff room with private front entrance. Kayak, swim, or bring your paddleboard or boa ...
From $191 per night (USD)Expedia
From $818 per night (USD)VRBO
Gem of the Berkshires. Mountain View. Short walk to lake & downtown.
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
A lovely property with gorgeous view of the Berkshire Mountains. Conveniently located near many attractions, such as Tan ...
From $818 per night (USD)VRBO
From $1035 per night (USD)VRBO
Casa Do Lago--Waterfront Home With Private Dock On Pontoosuc Lake
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 14
For 2023, a massive gut reno has been completed, adding a 24ft wide sunroom overlooking the lake, 2 new bedrooms and a b ...
From $1035 per night (USD)VRBO
From $631 per night (USD)VRBO
Chalet in the Berkshires, Wellness, Family, Lake, Kayaks, Sauna, EV charger & Home Office
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 10
Join our unique Berkshire vacation experience, away from the hustle and bustle: 🌟Kayak & swim on the lake 🌟Boost welln ...
From $631 per night (USD)VRBO
From $303 per night (USD)VRBO
Private Berkshire Cabin on 27acres near Jiminy Peak.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Secluded mountain home surrounded by 27 acres yet convenient to major attractions including Jiminy Peak, Williamstown, L ...
From $303 per night (USD)VRBO
From $468 per night (USD)VRBO
Farmhouse w AGA, 2 suites - close to GB & skiing
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Discover this enchanting folk Victorian farmhouse, a harmonious blend of vintage charm and modern convenience, just minu ...
From $468 per night (USD)VRBO
From $712 per night (USD)VRBO
Perfect family getaway spot! Free standing private 4 BR home on Jiminy Peak.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
100% private free standing house with private parking and entrance. No indoor common/shared areas. Quick walk thru woo ...
From $712 per night (USD)VRBO
From $1352 per night (USD)VRBO
Chic Modern Farmhouse 1 Mile to Downtown Lenox
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Our Designer Farmhouse has been lovingly updated and impressively furnished with careful thought and no expense spared. ...
From $1352 per night (USD)VRBO
From $989 per night (USD)VRBO
Spectacular 88-acre Berkshires Retreat w\/ Tennis Court - Family Friendly
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 9
Enjoy your vacation in a beautiful historic house located in the heart of the Berkshires. Located two and a quarter hour ...
From $989 per night (USD)VRBO
From $1005 per night (USD)VRBO
Luxury Berkshires Retreat in Lenox - Main House
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 11
A private retreat in Berkshires set on 5 acres in prime location in Lenox - our all-season property offers secluded luxu ...
From $1005 per night (USD)VRBO
From $744 per night (USD)VRBO
Spacious, Modern House 5 Bedrooms, 2.5 Bathrooms, Sleep 12 on small horse farm.
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Newly renovated house in the Southern Berkshires on small horse farm. Huge kitchen, 5 bedrooms. Close to Butternut mount ...
From $744 per night (USD)VRBO
From $269 per night (USD)VRBO
Modern secluded home in wooded Setting
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
This 2500 square foot home has an open floor plan downstairs with living-room kitchen and screen in porch at the back of ...
From $269 per night (USD)VRBO
From $411 per night (USD)VRBO
5 STAR CASUAL ELEGANCE for 5 STAR GUESTS
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
HYDRANGEA HILL - It doesn't get much better than this for style and proximity. Hydrangea Hill (circa, 1898) is located ...
From $411 per night (USD)VRBO
From $1739 per night (USD)VRBO
Charming, spacious country home with stunning views.....steps from Tanglewood!
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 8
Just steps to Tanglewood Main Gate and Kripalu from this dramatic three-story shingle style contemporary with five bedro ...
From $1739 per night (USD)VRBO
From $223 per night (USD)VRBO
\nPeaceful, Newly Renovated Lakeside Cottage On Lake Garfield In Berkshires
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Sweet, newly renovated cottage, in a blissfully tranquil setting on Lake Garfield in Monterey, MA. Secluded, private, ye ...
From $223 per night (USD)VRBO
From $324 per night (USD)VRBO
Spacious Berkshire Summer Rental, Private Dock on Lake 3 BR\/2b
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 7
Beautiful, spacious, 3 bedroom, 2 bathroom, family home in the Berkshires located on a private road on crystal clear Ric ...
From $324 per night (USD)VRBO
From $255 per night (USD)VRBO
Charming Downtown Williamstown Cottage - 5 Min Walk to Campus
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
This beautifully restored small home in the heart of Williamstown is the perfect location for visitors to the attraction ...
From $255 per night (USD)VRBO
From $620 per night (USD)VRBO
Spectacular setting on your own private lake close to it all!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
This is the perfect Berkshire home to swim, hike, leaf-peep, ski, sled, engage in the cultural attractions of the neighb ...
From $620 per night (USD)VRBO
From $422 per night (USD)VRBO
Enchanted Cottage On Babbling Brook
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
This turn of the century cottage is located on a 130 acre farm, it has total privacy and beautiful surrounding. The hous ...
From $422 per night (USD)VRBO
From $454 per night (USD)VRBO
A Fun Farmhouse Near Ski Butternut
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Our home is in the charming town of Great Barrington and its many unique shops and restaurants. It's very near mountains ...
From $454 per night (USD)VRBO
From $136 per night (USD)VRBO
Duplex in Historic Mill District Walkable to Williams & Spring St.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Up-and-coming neighborhood in the historic Mill Village district in Williamstown that is walkable to the Williams' campu ...
From $136 per night (USD)VRBO
From $298 per night (USD)VRBO
Lovely Lakefront Cottage, Peaceful Setting, Hiking And More
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This lovely lakefront cottage has been a favorite family gathering place of ours for 30 years. It sits on picturesque Lo ...
From $298 per night (USD)VRBO
From $589 per night (USD)VRBO
NEWLY RENOVATED THREE BEDROOM HAUS IN LENOX WITH MODERN INTERIOR DESIGN.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Modern, bright and renovated. Mid Century vogue furnishings, hardwood floors and central A/C are just some features you ...
From $589 per night (USD)VRBO
From $507 per night (USD)VRBO
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
- Bedrooms:
- 3
- Bathrooms:
- 8
- Sleeps:
- 28
Welcome.....we invite you to come enjoy the great space of our beautiful home with your family and friends in our unique ...
From $507 per night (USD)VRBO
From $307 per night (USD)VRBO
“Elterwater”-Swan lake. Your own lakefront oasis, a true Berkshire getaway
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 4
One of the very few waterfront homes available for rent. What other houses offer you 150 feet private lakefront where ...
From $307 per night (USD)VRBO
From $480 per night (USD)VRBO
Large Immaculate Home, 10 Minute Walk To Lenox Center, Minutes To Tanglewood
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Location, Location, Location 4 BR, 3½ bath immaculate property in Lenox available for rent. A ten minute walk from down ...
From $480 per night (USD)VRBO
From $475 per night (USD)VRBO
12 minutes to Butternut Skiing, Good For 3 Families with Hot Tub & Game Room
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
Beautiful country home with 3 bedrooms plus a kids loft, 6 minutes to Great Barrington with lots to discover. 12 minutes ...
From $475 per night (USD)VRBO
From $532 per night (USD)VRBO
Beautiful Two Bedroom, Ski In\/Out, Mountainside, Home away from Home!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Jiminy Peak - This beautiful and premium condo was just renovated for the 2016 ski season. It is fully equipped with eve ...
From $532 per night (USD)VRBO
From $663 per night (USD)VRBO
Cozy escape in the trees of the Berkshires
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
We are thrilled to share our country escape with you and hope you enjoy it as much as we do. Set on 5 acres of land, wit ...
From $663 per night (USD)VRBO
From $289 per night (USD)VRBO
Houghton Hill: Style and History in the Berkshires
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
Enjoy fresh air and warm sun at the top of Houghton Street. And it's an 8-minute walk to MASS MoCA and the town center. ...
From $289 per night (USD)VRBO
From $670 per night (USD)VRBO
Lakeside Home With Pool-Completely Renovated
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 16
On beautiful Lake Pontoosuc, this 100% renovated home is complete with a heated outdoor pool! Every detail has been att ...
From $670 per night (USD)VRBO
From $644 per night (USD)VRBO
Five-Star Family Friendly Townhouse in the Heart of Jiminy Peak
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Enjoy the Jiminy Peak Mountain Resort and explore the Berkshires during Spring, Summer, and Fall in this highly desirabl ...
From $644 per night (USD)VRBO
From $243 per night (USD)VRBO
Berkshire Gorge House, 15 minutes to Williamstown, 15 minutes to Jiminy Peak.
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 6
The Berkshire Gorge House is 15 minutes from Jiminy Peak Ski Area, 30 minutes to Bosquet’s Ski area in Pittsfield, an ho ...
From $243 per night (USD)VRBO
From $599 per night (USD)VRBO
Hip Renovated Mid Century 4 Bedroom on Long Bow Lake
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Drive down a lovely country dirt road to this recently renovated 4 bedroom, 2 bath mid century home on Long Bow Lake. Th ...
From $599 per night (USD)VRBO
From $662 per night (USD)VRBO
WINTER\/SUMMER - ON 5 ACRES, PRIVATE LAKE GARFIELD DOCK, 5 MILES FROM BUTTERNUT
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
We have done all we can to think of everything to ensure a great stay. Please review and let us know if you have any qu ...
From $662 per night (USD)VRBO
From $524 per night (USD)VRBO
Modern And Spacious Berkshires Retreat 5 bdrm 3 bath
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 11
This is a completely renovated 5 bedrooms and 3 baths house that is situated on a private street, 5 min drive to either ...
From $524 per night (USD)VRBO
From $770 per night (USD)VRBO
Waterfront Ashmere Lake House Near Berkshire Attractions
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Waterfront property on Ashmere Lake in Hinsdale, MA, with 4 bedrooms, an office, 3 bathrooms, screened in porch and a be ...
From $770 per night (USD)VRBO
From $647 per night (USD)VRBO
Light, Airy And Fabulous
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 5
This is a special place and it’s 3 minutes to Lake Garfield and 12 minutes to Butternut Ski Area! It's a very pretty an ...
From $647 per night (USD)VRBO
From $1135 per night (USD)VRBO
The Playhouse: 7k SqFt of Berkshires Modern Luxury & History, 15% OFF MARCH\/APR
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 20
15% OFF MARCH/APRIL 2025 RENTALS. PLEASE INQUIRE. ** Check out the Playhouse on the Netflix series The World's Most Am ...
From $1135 per night (USD)VRBO
From $523 per night (USD)VRBO
In the beautiful Berkshires, wheelchair-accessible home-20min toTanglewood \n\n\n
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 8
A wonderful Berkshire vacation home for the entire family to enjoy! This charming and spotless home is fully wheelchair/ ...
From $523 per night (USD)VRBO
From $259 per night (USD)Expedia
Renovated Downtown 1bedroom
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Located in the heart of historical downtown Lenox. A beautifully renovated space fully equipped for all your needs. The ...
From $259 per night (USD)Expedia
From $268 per night (USD)VRBO
Historical Downtown 1bedroom
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Located in the heart of historical downtown Lenox. A beautifully renovated space fully equipped for all your needs. The ...
From $268 per night (USD)VRBO
From $269 per night (USD)VRBO
Cozy Cottage on the Lake
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Relax in our rustic lake-front cottage for your next getaway in the Berkshires! Our small lake is perfect for kayaking, ...
From $269 per night (USD)VRBO
From $582 per night (USD)VRBO
Fantastic cottage in the Berkshire Mountains
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
Our incredible 4 bedroom log cabin is situated on 2 beautiful secluded acres in picture perfect Monterey - the ultimate ...
From $582 per night (USD)VRBO
From $377 per night (USD)VRBO
Brooksong, the perfect Berkshires getaway
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
*All bookings are subject to COVID-19 regulations by the state of Massachusetts. *Until regulations change, all guests ...
From $377 per night (USD)VRBO
From $150 per night (USD)VRBO
Vacation Village In The Berkshires 5 Star Resort - Suite B
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Gold Crown Resort! Spectacular mountain views, clubhouse, indoor pool, outdoor pool, game room, playground, kiddy pool, ...
From $150 per night (USD)VRBO
From $661 per night (USD)Expedia
Hidden Oasis in the Mountains by Evergreen Home
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
7 MINUTES FROM BOUSQUET MOUNTAIN SKI AREA Escape with family & friends to this hidden oasis in the heart of the Berkshir ...
From $661 per night (USD)Expedia
From $184 per night (USD)VRBO
Available for Healthcare and long term stays welcome 3 miles from Hospital
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 4
If you are coming to the area to help in one of our Hospitals or Healthcare facility please contact us for booking optio ...
From $184 per night (USD)VRBO
From $1353 per night (USD)Expedia
Private Estate, Heated Yearround Outdoor Pool
- Bedrooms:
- 5
- Bathrooms:
- 7
- Sleeps:
- 17
Summary: Awaiting your next trip in our former horse farm turned luxury vacation rental, recently upgraded and re-furnis ...
From $1353 per night (USD)Expedia
From $342 per night (USD)VRBO
Berkshires Hilltop Retreat w Magic View! 15 mins to Ski Butternut.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Please enjoy our little slice of paradise! Perched just up the hill from Lake Garfield, The Hupi House offers a truly ma ...
From $342 per night (USD)VRBO
From $363 per night (USD)Expedia
1500 sqft private entrance with beautiful views of the Berkshire Mountains
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Come enjoy a quiet getaway in Western Massachusetts. 2 bedrooms, (3 beds, 1 Queen, 1 Double and 1 twin) 1 bath, open ki ...
From $363 per night (USD)Expedia
From $313 per night (USD)VRBO
A Beautiful Log Cabin In The Woods, On Pontoosuc Lake, Yet Near Everything
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Greetings from John at the American House! This is the perfect getaway to destress and relax! This is an original Lincol ...
From $313 per night (USD)VRBO
From $489 per night (USD)Expedia
PRIVATE PENINSULA 2ac surrounded by water min from hiking skiing theater music
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 9
I JUST purchased my dream house! I have been searching for a lake house in the Berkshires for years & when this came on ...
From $489 per night (USD)Expedia
From $387 per night (USD)VRBO
Charming home in private Beachwood Community on Lake Mahkeenac, Stockbridge
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
This 3 bedroom, 1 bathroom home of 1000 square feet with an additional 200 square foot screened in porch with a table fo ...
From $387 per night (USD)VRBO
From $389 per night (USD)VRBO
Berkshires Retreat: Firepit, Grill, Screened Deck!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to where comfort meets convenience in the heart of the Berkshires! Just 1.5 miles from Tanglewood, 5 minutes to ...
From $389 per night (USD)VRBO
From $729 per night (USD)VRBO
11 acre mid-century estate, newly renovated, seasonally available pool.
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Rare 11 acre private estate close to the center of town. Designed by renowned NYC architect David Todd in the late 60s, ...
From $729 per night (USD)VRBO
From $1011 per night (USD)Expedia
The Great Escape Ski Cottage w\/HOT TUB @ Great Barrington
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 16
Well appointed Vacation Cottage, newly renovated by the Owners; An Architect and an Interior Designer as a Modern Farmho ...
From $1011 per night (USD)Expedia
From $245 per night (USD)VRBO
Pleasant on Pleasant
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 1
Modern conveniences and fresh decor make this Victorian the perfect spot for your North Adams stay. Our "Pleasant House" ...
From $245 per night (USD)VRBO
From $266 per night (USD)VRBO
Berkshires Summer Rental - Lee\/Lenox
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
Sunny three bedroom condo available for summer rental , with two full baths. Shaded front porch and sunny rear deck wi ...
From $266 per night (USD)VRBO
From $706 per night (USD)VRBO
Luxurious Mountain Retreat - Private 40-Acre Family Haven
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
Enjoy total privacy at this cozy mountain home on 40 acres, just minutes from ski resorts and charming shops. With floo ...
From $706 per night (USD)VRBO
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Luxury Berkshire Estate: Proximity to all the best the Berkshires has to offer!
- Bedrooms:
- 7
- Bathrooms:
- 6
- Sleeps:
- 14
"Words can't describe the incredible experience our family had during the holiday season at this magnificent property." ...
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From $510 per night (USD)VRBO
Elegant 4 BR condo in Lenox, MA- completely new- 3 min from Tanglewood
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 9
Welcome to the beautiful Lakeside Condominiums at Fox Hollow in Lenox/Lee, MA. This newly furnished condo is spacious a ...
From $510 per night (USD)VRBO
From $457 per night (USD)VRBO
Mountainside: Large 3-level Jiminy Peak Home
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
From our easily accessible, newly renovated, fully equipped spacious home you can walk to the ski trails, hike and explo ...
From $457 per night (USD)VRBO
From $504 per night (USD)VRBO
CABIN FEVER IN STOCKBRIDGE
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Hello hip, glamping cabin! Our 2 bedroom 1.5 bath cottage has been fully remodeled. The decor is chic & bohemian cool! E ...
From $504 per night (USD)VRBO
From $325 per night (USD)VRBO
Konkapot Cottage, Pastoral Bliss With Wide Views
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Newly and totally renovated house, with modern appliances and bathrooms in the heart of the Berkshires. The house featur ...
From $325 per night (USD)VRBO
From $941 per night (USD)VRBO
Fabulous Renovated Log Cabin: the perfect family getaway
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Stunning log cabin in the Berkshires on 10 wooded acres complete with brand new 4 season hot tub, in-ground pool, pickle ...
From $941 per night (USD)VRBO
From $219 per night (USD)VRBO
Cozy renovated cabin in Williamstown, steps from hiking trails
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Originally built in the early 1900s, this cabin has been owned and lovingly maintained by the same family for over 50 ye ...
From $219 per night (USD)VRBO