Berkshire Area Rentals
From $395 per night (USD)VRBO
Urban Peak Escape, Lenox, MA
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Discover Urban Peak Escapes in Lenox, MA—a charming New England town in the Berkshires. Just 1 mile from Tanglewood and ...
From $395 per night (USD)VRBO
From $461 per night (USD)Expedia
Perfect Nature Haven In Great Barrington
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: Welcome to your home for the week in Great Barrington—a spacious, nature-surrounded retreat. Just a 2-minute dr ...
From $461 per night (USD)Expedia
From $178 per night (USD)VRBO
1 Bd - Vacation Village in the Berkshires
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Located in Hancock with commanding views of the Jiminy Peak ski area, Vacation Village in the Berkshires offers endless ...
From $178 per night (USD)VRBO
From $123 per night (USD)Expedia
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 $123 per night (USD)Expedia
From $175 per night (USD)VRBO
Charming 1 Bedroom - 4 Star Resort w/ heated pool, gym, wi-fi, lot's more!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
The Berkshire Mountain Lodge features one-bedroom condominiums equipped with modern amenities such as full kitchens an ...
From $175 per night (USD)VRBO
From $204 per night (USD)VRBO
Becket Home w/ 3-Season Porch: Walk to Lake Access
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 7
Unwind and embrace nature at this charming Becket vacation rental! With views of Lake Robinhood and a screened porch for ...
From $204 per night (USD)VRBO
From $177 per night (USD)VRBO
Amazing 2-bedroom apartment sunny and quiet in Great Barrington
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Historic home Nestled on a quiet street in downdown Great Barrington, just steps from the River Walk path, this enchanti ...
From $177 per night (USD)VRBO
From $842 per night (USD)Expedia
Breathtaking Post & Beam minutes from Jiminy Peak, Williamstown, Lenox & hiking
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
New listing from the owners of Sunny Pines!! Bright and spacious, 25 ft ceiling, Post & Beam home nestled in the middle ...
From $842 per night (USD)Expedia
From $189 per night (USD)VRBO
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Just bring your clothes and food! Everything else is here. Everything to cook with clean, shower, extra linens and blank ...
From $189 per night (USD)VRBO
From $487 per night (USD)VRBO
Lakefront Hinsdale Home ~ 10 Mi to Pittsfield!
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Treat your family to the ultimate getaway in the Berkshires at this beautiful vacation rental on Lake Ashmere! The 3-bed ...
From $487 per night (USD)VRBO
From $319 per night (USD)VRBO
Berkshire Holiday Home with Hot Tub & A+ Amenities
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Book your next vacation at our special Berkshire Holiday home set on several acres in the beautiful Berkshire Mountains ...
From $319 per night (USD)VRBO
From $490 per night (USD)VRBO
Lakefront Home on Pontoosuc Lake, the Berkshires
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Stunning Lakehouse: Lakefront property & house on 1-acre on Pontsoosuc Lake in western MA, 2600 sq.ft., 3 bedrooms / 2 ...
From $490 per night (USD)VRBO
Click For PricingVRBO
The Berkshires Basecamp
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
7min to Bear Town SF/Butternut Ski 26min to Tanglewood Solo Stove, 2 decks, screened porch 2-65in+55in Roku TVs, Arcade, ...
Click For PricingVRBO
From $365 per night (USD)Expedia
Charming Berkshire Farmhouse: Your Cozy Retreat Awaits!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Nestled on picturesque grounds, this modern and updated 3-bedroom home offers the perfect blend of comfort and luxury. E ...
From $365 per night (USD)Expedia
From $1227 per night (USD)VRBO
Serene 5-BR Retreat 9-Min to Catamount
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Summary: Gather your friends and family at this a luxurious 5-BR retreat. Nestled in the serene woodlands of the Berkshi ...
From $1227 per night (USD)VRBO
From $196 per night (USD)Expedia
Large 3-bedroom house with WiFi and AC in Great Barrington
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Located in Great Barrington, this superb house boasts 3 cozy bedrooms - one with a king bed, one with two twin beds, and ...
From $196 per night (USD)Expedia
From $433 per night (USD)VRBO
Solomon Ely Homestead - Charming Pittsfield Stay
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 7
Enjoy your stay at this 1847 New England farmhouse located just steps from downtown Pittsfield. Make yourself at home wi ...
From $433 per night (USD)VRBO
From $738 per night (USD)Expedia
The Race Mountain House
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
High on the slopes of Race Mountain, this spacious 4-bedroom villa offers sweeping east-facing views. In the early hours ...
From $738 per night (USD)Expedia
From $193 per night (USD)VRBO
Cozy 1-bedroom condo at ski resort with WiFi, fitness room, pool & hottub
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Relax in a comfortable and cozy space after a winter day on the ski slopes. Enjoy all of the amenities of the on premise ...
From $193 per night (USD)VRBO
From $433 per night (USD)VRBO
1 Mi to Dtwn: Cottage w/ Large Yard in Stockbridge
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Dog Friendly w/ Fee | Furnished Deck for Coffee Moments | Fireside Relaxation Nestled in the heart of Stockbridge, with ...
From $433 per night (USD)VRBO
From $250 per night (USD)VRBO
Club Wyndham Bentley Brook Resort - 2 Bedroom
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
*** Sanitation/Cleaning Update *** Wyndham resorts have always met the highest standards of cleanliness, and now we are ...
From $250 per night (USD)VRBO
From $284 per night (USD)Expedia
Family Ski House at Catamount !
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Experience the ultimate family ski getaway at this spacious 4-bedroom, 3-bath home across from Catamount Ski Area. With ...
From $284 per night (USD)Expedia
From $374 per night (USD)VRBO
- Lake Front 4 Bdr w/ Fast Internet! -
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Enjoy this spacious 4 bed, 4 bath home nestled on Lake Garfield in the beautiful Berkshires. Well-curated, clean, and pe ...
From $374 per night (USD)VRBO
From $780 per night (USD)Expedia
Spacious 4Bd Just a Block from Lake Mansfield!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Charming four bedroom house on the hill with convenient access to downtown Great Barrington. Just a few blocks to the b ...
From $780 per night (USD)Expedia
From $396 per night (USD)VRBO
Charming 3-BR Berkshires Timber Cottage
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: Gather your family and friends and experience the charm of this 3-BR cabin in Becket, MA. Featuring three bedro ...
From $396 per night (USD)VRBO
From $423 per night (USD)Expedia
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 $423 per night (USD)Expedia
From $338 per night (USD)VRBO
Spacious 4BR Central-Berkshires Home with POOL!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Spacious and comfortable home in a serene setting and ideal location. Whether you are coming for performing arts, museu ...
From $338 per night (USD)VRBO
From $574 per night (USD)Expedia
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 $574 per night (USD)Expedia
From $174 per night (USD)VRBO
Trail Access: Berkshires Gem w/ Rooftop Deck!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Walk to Restaurants | Pet Friendly w/ Fee | 6 Mi to Tanglewood Get the most out of your next Berkshires getaway when yo ...
From $174 per night (USD)VRBO
From $700 per night (USD)VRBO
Grand Berkshire Manor By Evergreen Home
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Welcome to The Manor – your refined escape to the tranquil beauty of the Berkshires. Discover a perfectly situated, spa ...
From $700 per night (USD)VRBO
From $454 per night (USD)VRBO
Grandparent’s Cottage 250 steps to the lake
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
4 bedrooms, sleeps 7, 2 living rooms, 2 full bathrooms, fully stocked kitchen; lawn chairs, beach towels, games, and bic ...
From $454 per night (USD)VRBO
From $484 per night (USD)VRBO
Walk to Ski Slopes: Jiminy Peak Resort Getaway!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Private Ski Locker On-Site | 2 Living Rooms | In-Unit Laundry | Forest Views | WFH Friendly The beauty and adventure of ...
From $484 per night (USD)VRBO
From $299 per night (USD)VRBO
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 $299 per night (USD)VRBO
From $457 per night (USD)Expedia
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 $457 per night (USD)Expedia
From $405 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 $405 per night (USD)VRBO
Click For PricingExpedia
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 $392 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 $392 per night (USD)VRBO
From $444 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 $444 per night (USD)Expedia
From $324 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 $324 per night (USD)VRBO
From $395 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 $395 per night (USD)Expedia
From $393 per night (USD)VRBO
New for 2025! Walk to Lenox Village - 1930s Cottage Charmer!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Autumn 2025! Come enjoy the fall color in the Berkshires / Lenox in this walk-to- town vintage charmer. Minimum 4 night ...
From $393 per night (USD)VRBO
From $406 per night (USD)VRBO
Close to Ski Areas and Apple Orchards- 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. 5-10 minutes from Butternut Ski Area and Otis Ridge, ...
From $406 per night (USD)VRBO
From $414 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 $414 per night (USD)VRBO
From $361 per night (USD)VRBO
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 $361 per night (USD)VRBO
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 $1163 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 $1163 per night (USD)VRBO
From $199 per night (USD)VRBO
Thanksgiving Mountain Lodge, Mass.- 1 BR 1 Ba. Bousquet Mt Ski 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 $199 per night (USD)VRBO
From $387 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 $387 per night (USD)Expedia
From $206 per night (USD)VRBO
Tranquil Lakeside Escape in the Berkshires
- Bedrooms:
- 2
- 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 $206 per night (USD)VRBO
From $190 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 $190 per night (USD)Expedia
From $654 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 $654 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 $729 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 $729 per night (USD)VRBO
From $179 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 $179 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 $260 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 $260 per night (USD)VRBO
From $299 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 $299 per night (USD)VRBO
From $506 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 $506 per night (USD)VRBO
From $298 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 $298 per night (USD)VRBO
From $306 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 $306 per night (USD)VRBO
From $193 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 $193 per night (USD)VRBO
From $367 per night (USD)Expedia
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)Expedia
From $193 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 $193 per night (USD)VRBO
From $105 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 $105 per night (USD)VRBO
From $150 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 $150 per night (USD)VRBO
From $105 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 $105 per night (USD)VRBO
From $105 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 $105 per night (USD)VRBO
From $105 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 $105 per night (USD)VRBO
From $105 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 $105 per night (USD)VRBO
From $810 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 $810 per night (USD)Expedia
From $751 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 $751 per night (USD)VRBO
From $363 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 $363 per night (USD)VRBO
From $897 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 $897 per night (USD)VRBO
From $1293 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 $1293 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 $1135 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 $1135 per night (USD)VRBO
From $285 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 $285 per night (USD)VRBO
From $349 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 $349 per night (USD)VRBO
From $237 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 $237 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 $602 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 $602 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 $432 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 $432 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 $469 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 $469 per night (USD)VRBO
From $1707 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 $1707 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 $506 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 $506 per night (USD)VRBO
From $545 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 $545 per night (USD)Expedia
From $315 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 $315 per night (USD)VRBO
From $482 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 $482 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 $314 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 $314 per night (USD)VRBO
From $790 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 $790 per night (USD)VRBO
From $739 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 $739 per night (USD)VRBO
From $614 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 $614 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
From $381 per night (USD)VRBO
Brooksong, the perfect Berkshires getaway
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
*All bookings are subject to COVID-19 regulations by the state of Massachusetts. *Until regulations change, all guests ...
From $381 per night (USD)VRBO
From $1171 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 $1171 per night (USD)VRBO