Berkshire Area Rentals
From $361 per night (USD)VRBO
Historic Susan B. Anthony Room - Cozy & Charming Stay
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
The Susan B. Anthony Room at The Cornell Inn offers a charming and cozy retreat in the heart of the Berkshires. This inv ...
From $361 per night (USD)VRBO
From $301 per night (USD)Expedia
Experience Timeless Elegance in The Edith Wharton Room!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
The Edith Wharton Room offers a refined and elegant retreat inspired by classic charm and modern comfort. This beautiful ...
From $301 per night (USD)Expedia
From $486 per night (USD)VRBO
Waterfront Cottage Retreat By Evergreen Home
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
This lakefront cottage offers year-round magic—whether you're soaking up the summer sun, admiring vibrant fall foliage, ...
From $486 per night (USD)VRBO
From $260 per night (USD)Expedia
4 Mi to Great Barrington: Berkshires Retreat!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Renovated Farmhouse in a Peaceful Location | Modern Upgrades w/ Vintage-Inspired Touches | Family Movie/Board Game Night ...
From $260 per night (USD)Expedia
From $363 per night (USD)VRBO
Hummingbird Haven is a Berkshires Retreat surrounded by Nature and Local Charm.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Hummingbird Haven is a thoughtfully designed 3,100-square-foot home crafted for comfort, creativity, and connection—with ...
From $363 per night (USD)VRBO
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Cozy 2-bedroom cabin in charming Becket with WiFi, AC
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
Escape to a charming cabin in Becket for a soothing retreat. This adorable 2-bedroom in a lake community offers all the ...
Click For PricingExpedia
From $330 per night (USD)VRBO
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
550 Sq. Ft , Dogs *only* friendly A-Frame cabin amongst the forest located in private lake community with neighborhood g ...
From $330 per night (USD)VRBO
From $427 per night (USD)Expedia
Richmond Ranch w/ Hot Tub by Evergreen Home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Charming 3-bedroom, 2-bath ranch in a quiet neighborhood. Enjoy one-level living with a sun-filled porch, deck, and hot ...
From $427 per night (USD)Expedia
From $309 per night (USD)VRBO
Charming Berkshires Retreat – Minutes to Williamstown
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Beautifully renovated home on a former farm with the Green River running through the backyard. Between Williamstown & Ne ...
From $309 per night (USD)VRBO
From $473 per night (USD)Expedia
Friendly Richmond Cottage with Private Yard
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Unwind in Pittsfield at this charming house. With 6 cozy bedrooms and 2 bathrooms, this welcoming property is perfect fo ...
From $473 per night (USD)Expedia
From $457 per night (USD)VRBO
Just listed for summer 2025! Walk to Lenox Village - 1930s Cottage Charmer!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Newly available BY THE WEEK for the first time during the highly sought after summer arts season - two months of summert ...
From $457 per night (USD)VRBO
From $413 per night (USD)VRBO
Private Mountain Retreat on 5 acres
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Enjoy a peaceful stay at this 4-bedroom house on the Monterey line. This gorgeous property features 1 king bed, 1 queen ...
From $413 per night (USD)VRBO
From $413 per night (USD)VRBO
6 Mi to Tanglewood: Peaceful Berkshire Apt!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Hike On-Site | Surrounded By Nature | Near Wineries & Historical Sites Make the most of your adventure in the Berkshire ...
From $413 per night (USD)VRBO
From $300 per night (USD)Expedia
1/2 Mi to Jiminy Peak: Condo w/ Pool & Hot Tub
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Fireside Relaxation | BBQ Ready | Dedicated Workspace | Near Hiking & Mountain Biking Nestled in the scenic Mountainsid ...
From $300 per night (USD)Expedia
From $215 per night (USD)VRBO
Cozy Becket Cottage Escape w/ Lake Access!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Nestled in nature and surrounded by wildlife, this Becket vacation rental offers the perfect setting for your dream outd ...
From $215 per night (USD)VRBO
From $171 per night (USD)Expedia
Charming 1-bedroom apartment in wonderful Lenox Dale
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Your Lenox getaway begins at this 1-bedroom apartment. Nestled in a fantastic location, this serene retreat features a c ...
From $171 per night (USD)Expedia
From $399 per night (USD)VRBO
Lake View Cozy Cottage
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Experience Pittsfield like a local in this 2-bedroom house. The bedrooms feature 2 queen beds, perfect for a tremendous ...
From $399 per night (USD)VRBO
From $140 per night (USD)Expedia
Oak 'n Spruce Resort 2 Bedrooms in The Berkshires an IHG and Holiday Inn Club
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Unwind in Lee at this marvelous resort. This cozy retreat features 2 bedrooms with a king and queen bed. You can look f ...
From $140 per night (USD)Expedia
From $312 per night (USD)VRBO
Tranquil Lakeside Escape in the Berkshires
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
Retreat to this spacious 2-bedroom condo at The Ponds at Foxhollow, nestled in the scenic Berkshires of Massachusetts. P ...
From $312 per night (USD)VRBO
From $192 per night (USD)Expedia
Peaceful 1BR Condo with Pond View
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 4
Escape to a serene retreat at this cozy 1-bedroom condo in The Ponds at Foxhollow, nestled in the heart of the Berkshire ...
From $192 per night (USD)Expedia
From $215 per night (USD)VRBO
Thanksgiving in Pittsfield, Mass.- 1 BR 1 Ba. Snow & More! 11/26-11/29/2025
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Berkshire Mountain Lodge is a family vacation destination for all seasons. Surrounded by beautiful countryside, historic ...
From $215 per night (USD)VRBO
From $386 per night (USD)Expedia
Charming 3-bedroom condo with WiFi in Williamstown, MA
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This fabulous condo in Williamstown offers 3 adorable bedrooms with queen beds, 2 brilliant bathrooms featuring a bathtu ...
From $386 per night (USD)Expedia
From $221 per night (USD)VRBO
Butterfly Bungalow! Charming 2-bedroom Cabin and Studio in delightful Otis, MA
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Butterfly Bungalow, a peaceful woodland retreat in the Berkshires. Nestled among native perennials and whispe ...
From $221 per night (USD)VRBO
From $216 per night (USD)Expedia
Berkshire Cabin by Lake Ashmere
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Come stay at this comfortable, private cottage at Lake Ashmere in the Berkshires. There’s lake access with a short walk ...
From $216 per night (USD)Expedia
From $711 per night (USD)VRBO
Spacious 5-bedroom house in charming Lee with WiFi
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 15
Welcome to Lee Manor – Your Cozy Retreat in the Heart of the Berkshires. Located in the charming town of Lee, Massachuse ...
From $711 per night (USD)VRBO
From $183 per night (USD)Expedia
The Serendipity Spot
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Greetings from the Serendipity Spot where old meets new in this charming, elegant & peaceful space where you may rest, l ...
From $183 per night (USD)Expedia
From $1038 per night (USD)VRBO
Gorgeous Williamstown Estate 6BD/5BA
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 16
Magnificent estate, ideal for family gatherings and retreats! This 5,300 sqft house offers ample space to sleep, hang ou ...
From $1038 per night (USD)VRBO
From $243 per night (USD)Expedia
Berkshires Cottage + Trails & Water Nearby
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Family-friendly rustic-modern getaway set on 4 private acres in the heart of the Berkshires. We designed this home as a ...
From $243 per night (USD)Expedia
From $599 per night (USD)VRBO
Newly Renovated Lakefront Haven In Lenox
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: Newly renovated lakefront getaway on beautiful and serene Laurel Lake in Lenox! This spacious 4-bedroom, 3-bath ...
From $599 per night (USD)VRBO
From $919 per night (USD)VRBO
Lakeside Estate: 2 Homes For Family Gatherings
- Bedrooms:
- 5
- Bathrooms:
- 8
- Sleeps:
- 18
Summary: Stay tonight and book two houses across the street from each other—perfect for large families! Together: 8 bedr ...
From $919 per night (USD)VRBO
From $880 per night (USD)VRBO
Bright & beautiful lakefront retreat. 5 minute walk to Tanglewood!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
3BR/2.5BA Sun-filled interiors: soaring ceilings & walls of windows frame surrounding forrest. 5-min walk to Tanglewood. ...
From $880 per night (USD)VRBO
From $367 per night (USD)VRBO
Weekend at Bentley Brooks Resort, Hancock, MA
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 8
Welcome to Bentley Brook, a first-class resort nestled at the base of Jiminy Peak. Whether you're here for a weekend of ...
From $367 per night (USD)VRBO
From $574 per night (USD)VRBO
Williamstown Stay, Minutes To Williams College
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Modern home in a quiet neighborhood, minutes from Williams College and an easy drive to top restaurants, the Cl ...
From $574 per night (USD)VRBO
From $1132 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 $1132 per night (USD)VRBO
From $188 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 $188 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 $189 per night (USD)VRBO
All Season Adventures, Ski In/Ski Out, Wyndham Bentley Brook 2 Bedroom Dlx.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Get ready for an unforgettable family escape at Wyndham Bentley Brook, where breathtaking natural beauty and year-round ...
From $189 per night (USD)VRBO
From $256 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 $256 per night (USD)VRBO
From $312 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 $312 per night (USD)VRBO
From $413 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 $413 per night (USD)VRBO
From $481 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 $481 per night (USD)VRBO
From $603 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 $603 per night (USD)VRBO
From $393 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 $393 per night (USD)VRBO
From $214 per night (USD)VRBO
All Season Adventures, Ski In/Ski Out, Wyndham Bentley Brook 2 Bedroom Dlx.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Get ready for an unforgettable family escape at Wyndham Bentley Brook, where breathtaking natural beauty and year-round ...
From $214 per night (USD)VRBO
From $482 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 $482 per night (USD)VRBO
From $408 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 $408 per night (USD)VRBO
From $323 per night (USD)VRBO
All Season Adventures, Ski In/Ski Out, Wyndham Bentley Brook 2 Bedroom Dlx.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Get ready for an unforgettable family escape at Wyndham Bentley Brook, where breathtaking natural beauty and year-round ...
From $323 per night (USD)VRBO
From $197 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 $197 per night (USD)VRBO
From $199 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 $199 per night (USD)VRBO
From $199 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 $199 per night (USD)VRBO
From $197 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 $197 per night (USD)VRBO
From $199 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 $199 per night (USD)VRBO
From $361 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 $361 per night (USD)VRBO
From $114 per night (USD)VRBO
1br Deluxe Condo Jiminy Peak Skiing!
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 8
Summary: This resort at the base of Jiminy Peak Ski Mountain is an excellent choice for mountainside recreation. It prov ...
From $114 per night (USD)VRBO
From $143 per night (USD)VRBO
2br DX Condo Ski & Berkshire County!
- 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 $143 per night (USD)VRBO
From $114 per night (USD)VRBO
1br Deluxe Condo Jiminy Peak Skiing!
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 8
Summary: This resort at the base of Jiminy Peak Ski Mountain is an excellent choice for mountainside recreation. It prov ...
From $114 per night (USD)VRBO
From $114 per night (USD)VRBO
1br Deluxe Condo Jiminy Peak Skiing!
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 8
Summary: This resort at the base of Jiminy Peak Ski Mountain is an excellent choice for mountainside recreation. It prov ...
From $114 per night (USD)VRBO
From $114 per night (USD)VRBO
1br Deluxe Condo Jiminy Peak Skiing!
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 8
Summary: This resort at the base of Jiminy Peak Ski Mountain is an excellent choice for mountainside recreation. It prov ...
From $114 per night (USD)VRBO
From $114 per night (USD)VRBO
1br Deluxe Condo Jiminy Peak Skiing!
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 8
Summary: This resort at the base of Jiminy Peak Ski Mountain is an excellent choice for mountainside recreation. It prov ...
From $114 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 $738 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 $738 per night (USD)VRBO
From $783 per night (USD)Expedia
Gem of the Berkshires. Mountain View. Short walk to lake & downtown.
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
A lovely property with gorgeous view of the Berkshire Mountains. Conveniently located near many attractions, such as Tan ...
From $783 per night (USD)Expedia
From $579 per night (USD)VRBO
Casa Do Lago--Waterfront Home With Private Dock On Pontoosuc Lake
- Bedrooms:
- 3
- 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 $579 per night (USD)VRBO
From $604 per night (USD)VRBO
Chalet in the Berkshires, Wellness, Hike, Sauna, Gas Fireplace, EV charger & Home Office
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Unique Berkshire vacation experience, away from the hustle and bustle: 🍁Boost your wellness in the barrel Sauna 🍁Relax ...
From $604 per night (USD)VRBO
From $308 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 $308 per night (USD)VRBO
From $1367 per night (USD)VRBO
Chic Modern Farmhouse 1 Mile to Downtown Lenox
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Our Designer Farmhouse has been lovingly updated and impressively furnished with careful thought and no expense spared. ...
From $1367 per night (USD)VRBO
From $1005 per night (USD)VRBO
Spectacular 88-acre Berkshires Retreat w/ Tennis Court - Family Friendly
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
Enjoy your vacation in a beautiful historic house located in the heart of the Berkshires. Located two and a quarter hour ...
From $1005 per night (USD)VRBO
From $1117 per night (USD)VRBO
Luxury Berkshires Retreat in Lenox - Main House
- Bedrooms:
- 3
- 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 $1117 per night (USD)VRBO
From $866 per night (USD)VRBO
Spacious, Modern House 5 Bedrooms, 2.5 Bathrooms, Sleep 12 on small horse farm.
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 12
Newly renovated house in the Southern Berkshires on small horse farm. Huge kitchen, 5 bedrooms. Close to Butternut mount ...
From $866 per night (USD)VRBO
From $283 per night (USD)VRBO
Modern secluded home in wooded Setting
- Bedrooms:
- 2
- 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 $283 per night (USD)VRBO
From $503 per night (USD)VRBO
5 STAR CASUAL ELEGANCE for 5 STAR GUESTS
- Bedrooms:
- 2
- 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 $503 per night (USD)VRBO
From $244 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 $244 per night (USD)VRBO
From $324 per night (USD)VRBO
Spacious Berkshire Summer Rental, Private Dock on Lake 3 BR/2b
- Bedrooms:
- 2
- Bathrooms:
- 3
- 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 $246 per night (USD)VRBO
Charming Downtown Williamstown Cottage - 5 Min Walk to Campus
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
This beautifully restored small home in the heart of Williamstown is the perfect location for visitors to the attraction ...
From $246 per night (USD)VRBO
From $634 per night (USD)VRBO
Spectacular setting on your own private lake close to it all!
- Bedrooms:
- 3
- 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 $634 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 $492 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 $492 per night (USD)VRBO
From $558 per night (USD)Expedia
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 $558 per night (USD)Expedia
From $316 per night (USD)VRBO
“Elterwater”-Swan lake. Your own lakefront oasis, a true Berkshire getaway
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
One of the very few waterfront homes available for rent. What other houses offer you 150 feet private lakefront where ...
From $316 per night (USD)VRBO
From $479 per night (USD)VRBO
Large Immaculate Home, 10 Minute Walk To Lenox Center, Minutes To Tanglewood
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Location, Location, Location 4 BR, 3½ bath immaculate property in Lenox available as a short-term rental. A ten minute ...
From $479 per night (USD)VRBO
From $465 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 $465 per night (USD)VRBO
From $542 per night (USD)VRBO
Beautiful Two Bedroom, Ski In/Out, Mountainside, Home away from Home!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Jiminy Peak - This beautiful and premium condo was just renovated for the 2016 ski season. It is fully equipped with eve ...
From $542 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 $509 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 $509 per night (USD)VRBO
From $436 per night (USD)VRBO
A Fun Farmhouse Near Ski Butternut
- Bedrooms:
- 2
- 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 $436 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 $752 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 $752 per night (USD)VRBO
From $1739 per night (USD)VRBO
Charming, spacious country home with stunning views.....steps from Tanglewood!
- Bedrooms:
- 5
- 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 $312 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 $312 per night (USD)VRBO
From $796 per night (USD)VRBO
Lakeside Home With Pool-Completely Renovated
- Bedrooms:
- 4
- 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 $796 per night (USD)VRBO
From $683 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 $683 per night (USD)VRBO
From $250 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 $250 per night (USD)VRBO
From $587 per night (USD)VRBO
WINTER/SUMMER - ON 5 ACRES, PRIVATE LAKE GARFIELD DOCK, 5 MILES FROM BUTTERNUT
- Bedrooms:
- 2
- Bathrooms:
- 4
- 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 $587 per night (USD)VRBO
From $647 per night (USD)VRBO
Light, Airy And Fabulous
- Bedrooms:
- 2
- 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 $1104 per night (USD)VRBO
The Playhouse: 7,000 Sq Ft of Berkshires Modern Luxury & History
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 20
** Check out the Playhouse on the Netflix series The World's Most Amazing Vacation Rentals. It's included in the Gourmet ...
From $1104 per night (USD)VRBO
From $683 per night (USD)VRBO
In the beautiful Berkshires, wheelchair-accessible home-20min toTanglewood \n\n\n
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 8
A wonderful Berkshire vacation home for the entire family to enjoy! This charming and spotless home is fully wheelchair/ ...
From $683 per night (USD)VRBO
From $572 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 $572 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 $337 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 $337 per night (USD)VRBO
From $582 per night (USD)Expedia
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)Expedia