Berkshire Area Rentals
From $489 per night (USD)VRBO
Berkshires Lakefront Retreat\n
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Catch your breath…and let nature take it away again... Private and serene, our beautiful lakefront home is your idylli ...
From $489 per night (USD)VRBO
Click For PricingExpedia
Woodland Haven w\/ Heated Pool by Evergreen Home
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 5
Recently renovated, this gorgeous 2BR-3BA home features vaulted ceilings, beautiful wood beams, gorgeous stone fireplace ...
Click For PricingExpedia
Click For PricingVRBO
Guest House Sanctuary by Evergreen Home
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Beautiful haven in the woods. The 2BR guest house is currently available for up to 5 guests. Surrounded by nature, this ...
Click For PricingVRBO
Click For PricingExpedia
Cheever Hollow Farm an essential retreat central to Lenox and the Berkshires
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 7
Welcome to Cheeverhollowfarm in picturesque Richmond/Lenox. Please Contact me for specific details or requests. We are ...
Click For PricingExpedia
From $223 per night (USD)VRBO
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Nestled in the wooded hills of the Berkshire Mountains, this outdoor-oriented resort offers year-round fun. Miles of be ...
From $223 per night (USD)VRBO
From $229 per night (USD)Expedia
Cozy 1-bedroom at a New England style resort in the Berkshire mountains
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This amazing 1-bedroom resort in Hancock is perfect for your mountain escape. With a king bed, fireplace, a convenient s ...
From $229 per night (USD)Expedia
From $341 per night (USD)VRBO
Berkshire Blue House - sleeps 6!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Berkshire getaway! This 3-bedroom house sleeps 6. It has 2 bathrooms and a large deck. Two of the spacious bedrooms h ...
From $341 per night (USD)VRBO
From $798 per night (USD)Expedia
Fabulous modern home with pool & separate guest house . Pet-friendly!
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Sunny modern home with separate luxury guest house. 3 lovely bedrooms in main house, 2 with en-suite bathrooms, tasteful ...
From $798 per night (USD)Expedia
From $235 per night (USD)VRBO
Modern 3-bedroom home in the Berkshires!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Relax with the whole family at this peaceful Berkshire getaway. Located within a short car ride from Sheffield, Great Ba ...
From $235 per night (USD)VRBO
From $443 per night (USD)VRBO
Berkshire Cottage - seasonal rentals highly encouraged!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Perfect Berkshire getaway. Minutes from downtown Great Barrington and Stockbridge, Tanglewood, Rockwell Museum, multipl ...
From $443 per night (USD)VRBO
From $690 per night (USD)VRBO
Ray of Sunshine Berkshire Home on Pontoosuc Lake
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 14
Brand new construction directly on Lake Pontoosuc. This home sleeps 14 guests. There is a brand new chef’s kitchen! Th ...
From $690 per night (USD)VRBO
From $530 per night (USD)VRBO
Contemporary 3-bedroom home with views, fireplace & close to Butternut Ski area
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Guests can take in the view from the front porch, and the house has plenty of space, including the basement game room an ...
From $530 per night (USD)VRBO
From $224 per night (USD)VRBO
Great Place - 2 BD - Kitchen and Pool
- 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 ...
From $224 per night (USD)VRBO
From $560 per night (USD)VRBO
Beautiful Berkshire Home - Enjoy summer, fall & winter attractions
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 7
Family or couples getaway! 3 bedrooms plus library, Sleeps 6-8 A beautiful 3050 Sq. Ft., 2-Story Colonial and attached ...
From $560 per night (USD)VRBO
From $213 per night (USD)VRBO
Relaxing retreat in the Berkshires! Perfect for outdoor enthusiast!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Come and spend a weekend relaxing by a fire or exploring the many restaurants and outdoor activities from this unique an ...
From $213 per night (USD)VRBO
From $192 per night (USD)VRBO
Great Place - 2 BD - Kitchen - Pool
- 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 ...
From $192 per night (USD)VRBO
From $287 per night (USD)VRBO
A spacious Log Home on 11+ Acres of Private Forest 5 minutes from Ski Butternut
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 8
A private oasis on 11 forested acres on the backside of Butternut Mountain. Whether for skiing in the winter or hiking ...
From $287 per night (USD)VRBO
From $210 per night (USD)VRBO
Charming cottage in the heart of the Berkshires!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
A lovely, quiet retreat for two or a fun family getaway, just minutes from some of the most iconic spots in the Berkshir ...
From $210 per night (USD)VRBO
From $357 per night (USD)VRBO
Mid-Century Modern Berkshires Getaway on 6.5 Acres!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Explore The Berkshires while staying in a beautiful mid- century modern deck house. Nestled within nature on a premier r ...
From $357 per night (USD)VRBO
From $527 per night (USD)Expedia
Modern Cabin Near Tanglewood
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
Welcome to West Stockbridge in the Berkshires! This newly renovated modern cabin is nestled amongst the trees and locate ...
From $527 per night (USD)Expedia
From $847 per night (USD)VRBO
2 Bedroom Condo, at Jiminy Peak Ski Mountain, Bentley Brook Resort!!
- 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 $847 per night (USD)VRBO
Click For PricingExpedia
2 Bedroom Deluxe Condo at Jiminy Peak Mountain, Skiing, Bentley Brook Resort!
- 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 ...
Click For PricingExpedia
From $840 per night (USD)VRBO
2 Bedroom Deluxe Condo w\/ Kitchen, at Jiminy Peak Ski Mountain, Bentley Brook!
- 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 $840 per night (USD)VRBO
From $808 per night (USD)VRBO
2 Bedroom Deluxe Condo at Jiminy Peak Ski Mountain, Bentley Brook Resort!
- 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 $808 per night (USD)VRBO
Click For PricingVRBO
A Cozy 100 yr old New England Berkshires Dutch Colonial.\n\nLong term available.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Cozy New England Dutch Colonial on a large corner 1/2 acre lot, closed in with fence and gate to close in driveway, sur ...
Click For PricingVRBO
Click For PricingExpedia
Bentley Brook at Jiminy Peak - 2 Bedroom - ski in\/out
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Ski-In/Ski-Out Plus Year-Round Mountainside Fun. Wyndham Bentley Brook is situated right at the base of Jiminy Peak ski ...
Click For PricingExpedia
From $411 per night (USD)VRBO
Great Pet Friendly Condo at Jiminy Peak for all Seasons
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 7
Beautiful condo at Jiminy Peak's Country Village. Two-bedroom condo with a full bath and laundry, completely renovated i ...
From $411 per night (USD)VRBO
From $646 per night (USD)VRBO
Beautiful House In The Woods, Huge Yard, Hot Tub
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Come enjoy country living in all seasons – on 4+ acres on a private lane yet only minutes to Downtown Great Bar ...
From $646 per night (USD)VRBO
From $426 per night (USD)VRBO
Quintessential 1860's Berkshire farmhouse with mountain views on 30 acres.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 7
Charming 1860's farmhouse with spectacular mountain & meadow views situated on more than 30 acres. Large, covered porch ...
From $426 per night (USD)VRBO
From $361 per night (USD)VRBO
Historic 2 Bedroom Apt; Heart of The Berkshires
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Built in 1774, The Elm Court Inn is the perfect balance of old and new. Enjoy all the charm of staying in a historic lan ...
From $361 per night (USD)VRBO
From $621 per night (USD)VRBO
Wyndham Bentley Brook Condo Resort
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 8
Nestled in the Berkshire Mountains at the base of Jiminy Peak Ski Mountain, Wyndham Bentley Brook takes "weekend getaway ...
From $621 per night (USD)VRBO
From $388 per night (USD)VRBO
Designer Berkshire Cottage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This is what ‘Tiny Home’ Dreams are made of! Our Renovated Designer Cottage located in rural Richmond Massachusetts is c ...
From $388 per night (USD)VRBO
From $191 per night (USD)VRBO
Summer in the Berkshires!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Spend the SUMMER in the HEART of the BERKSHIRES! Just minutes from both the Lenox and Stockbridge Town Beach with access ...
From $191 per night (USD)VRBO
From $238 per night (USD)VRBO
Central Haus (Group getaway on a quiet street)
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
Beautifully designed house on a lovely, quiet street, with a view of Mt. Greylock. Three-minute drive to MassMoCA, six-m ...
From $238 per night (USD)VRBO
From $4446 per night (USD)VRBO
Ultra Luxury new home in Berkshires\/ 3 miles from Williams College
- Bedrooms:
- 8
- Bathrooms:
- 7
- Sleeps:
- 16
Set on 35 acres with spectacular views and total privacy. This property really speaks for itself. It is perfect for an ...
From $4446 per night (USD)VRBO
From $272 per night (USD)Expedia
51 Church Street, Lenox MA - One Bedroom Unit
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Refined getaway Newly renovated downtown space fully equipped for all your needs. The kitchen has an array of cooking es ...
From $272 per night (USD)Expedia
From $536 per night (USD)VRBO
Farmhouse-Loft -48 Main Street, Lenox, MA
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Located on Main Street in downtown Lenox. A beautifully renovated space fully equipped for all your needs. The eat-in ki ...
From $536 per night (USD)VRBO
From $1301 per night (USD)VRBO
Renovated family friendly house close to everything and endless views
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Bright, comfortable house with pool and comfortable outdoor seating and eating areas, endless mountain views in front an ...
From $1301 per night (USD)VRBO
From $403 per night (USD)VRBO
Snowdrop Lodge - Beautiful Condo on Jiminy Peak Grounds
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Beautifully renovated berkshire condo within Jiminy Peak grounds. Corner unit with ample parking, only a short walk to s ...
From $403 per night (USD)VRBO
From $1132 per night (USD)VRBO
Serene Retreat in the Scenic Berkshire Mountains\n
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Located in the scenic Berkshire Mountains, our condo resort offers a perfect retreat for those seeking relaxation, outdo ...
From $1132 per night (USD)VRBO
From $351 per night (USD)VRBO
Pine View Cottage, Berkshires Getaway Lake Buel w\/ lake rights. Pet friendly!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Recently renovated home in the exclusive Lake Buel community very close to the Appalachian Trail, Butternut Ski Area, Do ...
From $351 per night (USD)VRBO
From $573 per night (USD)VRBO
Modern, Renovated Lakefront Escape
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
Located in the heart of the Berkshires, and situated on the beautiful Richmond Pond, East Beach Lakehouse is a stylish, ...
From $573 per night (USD)VRBO
From $482 per night (USD)VRBO
Ski season is here!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Clean and bright, this updated unit is located in the heart of Jiminy and offers impeccable comfort and convenience. Pa ...
From $482 per night (USD)VRBO
From $523 per night (USD)VRBO
Family Friendly in Sheffield, private yet close to everything!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Your perfect country escape. Clean, spacious, light and airy home set in the middle of a meadow on 20 acres. Complete pr ...
From $523 per night (USD)VRBO
From $488 per night (USD)VRBO
An In-Town Beauty with Late Checkout
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
The Berkshires and all its attractions are at your doorstep in this newly renovated, well-insulated 1900 Victorian, situ ...
From $488 per night (USD)VRBO
From $862 per night (USD)Expedia
Lake Buel Lakefront - 4 Bedrooms with private dock
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Idyllic Berkshire lakeside 4 bedroom cottage offering swimming, fishing, water sports and hiking. Located directly on t ...
From $862 per night (USD)Expedia
From $657 per night (USD)VRBO
MLK weekend available! Ski in\/out - Jiminy Peak Wyndham Bentley Brook
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
I pre-reserved the Pres and MLK weekend Fri to Monday for your family! Luxury Room is right on Jiminy Peak's learning/b ...
From $657 per night (USD)VRBO
From $1243 per night (USD)Expedia
Panoramic Views, Indoor Pool by Evergreen Home
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 11
An ideal retreat nestled in the Berkshires with vast, expansive panoramic views. With 4 BR, 4.5 BA, a brand new gorgeous ...
From $1243 per night (USD)Expedia
From $190 per night (USD)VRBO
Stay at Beaver Lodge!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This secluded and private one-bedroom cottage has two gas stoves to keep you toasty in winter and A/C to keep you cool i ...
From $190 per night (USD)VRBO
From $477 per night (USD)Expedia
Private Berkshires Home On 5+ Acres, Rustic & Chic
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 12
Summary: Enjoy the beauty of the Berkshires in our tranquil retreat! The home, with rustic charm and modern touches, fea ...
From $477 per night (USD)Expedia
From $348 per night (USD)VRBO
Pres day weekend! STUDIO Sleeps 4 Ski in\/out Wyndham Bentley Brook JIminy
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 8
I pre-reserved President and MLK weekend Friday to Monday for your family. Luxury Room is right on Jiminy Peak's learni ...
From $348 per night (USD)VRBO
From $1392 per night (USD)VRBO
The Brookman: Renovated 6000 SF Estate On 40 Acres
- Bedrooms:
- 5
- Bathrooms:
- 7
- Sleeps:
- 16
Summary: Previously owned by one of Hollywood’s most iconic actors, this 6,000 SF estate sits on 40 secluded acres with ...
From $1392 per night (USD)VRBO
From $699 per night (USD)VRBO
Private Fall and Winter Berkshires Retreat
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Enjoy the fall and winter at our newly remodeled 4 bedroom, 2 ½ bath home that is nestled among the farms just outside t ...
From $699 per night (USD)VRBO
Click For PricingExpedia
Remodeled ski and summer retreat close to town
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Situated just minutes from the town of Great Barrington, skiing at Butternut & beautiful hiking trails, you will find th ...
Click For PricingExpedia
Click For PricingVRBO
Berkshires sanctuary close to museums and nature
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
Private first story of a house located in North Adams, just one mile away from Williamstown, 10 minutes away from the Ap ...
Click For PricingVRBO
From $209 per night (USD)VRBO
2 bedroom Riverhouse in the Heart of the Berkshires
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Located between the villages of Stockbridge, Housatonic and Great Barrington. Most unique Riverhouse property located on ...
From $209 per night (USD)VRBO
Click For PricingVRBO
Home in The Berkshires - Becket
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
New house in Becket. The house is located in the heart of Berkshire where all the cultural activities are around: Jacob' ...
Click For PricingVRBO
From $212 per night (USD)VRBO
Charming Berkshire Getaway in a Modern Comfortable House
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
Beautiful 3 bedroom ranch style house decorated in mid century modern style. Kitchen and bathrooms are brand new along w ...
From $212 per night (USD)VRBO
From $1390 per night (USD)VRBO
Historic (updated)1812 Federal brick house well situated in Berkshires with pool
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Historic fully updated brick house originally built in 1812 in the Berkshires in Western Massachusetts on one of the pre ...
From $1390 per night (USD)VRBO
From $355 per night (USD)VRBO
New Listing Contemporary Cottage in the Woods viewing a Private Spring Fed Pond
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Our Tree House in the Berkshires has a view of the forest out every window. Our home overlooks a spring fed pond and is ...
From $355 per night (USD)VRBO
From $503 per night (USD)VRBO
Beautiful, peaceful modern home in a wooded area with lake access
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 6
Supremely relaxing modern home in wooded setting with screened in outdoor porch as well as a firepit, patio and gas gri ...
From $503 per night (USD)VRBO
From $1250 per night (USD)VRBO
Stockbridge Estate with Mountain Views
- Bedrooms:
- 6
- Bathrooms:
- 4
- Sleeps:
- 8
Available for the week of LABOR DAY 2023. Completely reserved for June, July & August 2023. The estate is located a 5-mi ...
From $1250 per night (USD)VRBO
From $450 per night (USD)VRBO
Relaxing Getaway in the Beautiful Berkshires
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
A wonderful family country escape with all the accommodations of home! Set on two sprawling acres in the beautiful Berks ...
From $450 per night (USD)VRBO
From $401 per night (USD)Expedia
Best of the Berkshires + Hot Tub by Evergreen Home
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Ski, hike, shop, and dine with this beautiful 2-bed, 1-bath Berkshires cottage as your home base. 15 minutes to the slop ...
From $401 per night (USD)Expedia
From $458 per night (USD)VRBO
Enjoy a renovated private home right in downtown Lenox
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Our lovely home is literally a stones throw from Lenox's downtown shops and fabulous restaurants but also in a very quie ...
From $458 per night (USD)VRBO
From $456 per night (USD)Expedia
West Stockbridge Sanctuary by Evergreen Home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Enjoy a getaway to the Berkshires in this magnificent post & beam home; newly renovated and nestled on 1 acre of land - ...
From $456 per night (USD)Expedia
From $914 per night (USD)VRBO
Newly renovated townhouse, sleeps 8 located at Jiminy Peak Ski Resort
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Let this newly renovated 3-bedroom, 2-bathroom townhouse, with European finishes, sky lights and brand new kitchen, bath ...
From $914 per night (USD)VRBO
From $452 per night (USD)VRBO
Family-friendly, private three bedroom cottage in the beautiful Berkshires
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Rustic cottage on hill accessed by private lane Located in beautiful Berkshire Mountains of western, MA Simple, charming ...
From $452 per night (USD)VRBO
From $428 per night (USD)VRBO
Stonebridge Cabin: Modern Amenities, Enjoy Nature!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Our quiet, peaceful and nestled in the woods, is a meticulously updated modern retreat offers the quiet comfort ...
From $428 per night (USD)VRBO
From $932 per night (USD)VRBO
Historic Stockbridge Villa on 25 acres sleeps 23
- Bedrooms:
- 7
- Bathrooms:
- 12
- Sleeps:
- 23
At the end of a tree-lined driveway, this huge private eleven bedroom villa sits by the edge of a field with garden and ...
From $932 per night (USD)VRBO
From $1088 per night (USD)VRBO
Perfect setting for Family Vacations Short and Long Term Stays Welcomed.
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
Private Estate Centrally located to all Berkshire attractions and just mins. from the Mass Pike. Perfect for any event. ...
From $1088 per night (USD)VRBO
From $300 per night (USD)Expedia
Charming, Quiet, River Front
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 13
A cozy modern log cabin nestled in the hills of the Berkshires in a large wooded area with landscaped yard and fishpond. ...
From $300 per night (USD)Expedia
From $457 per night (USD)VRBO
Best of the Berkshires & Hudson Valley
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Located in Canaan, NY, less than a mile from the Massachusetts border, this wonderful 1700s post and beam farmhouse has ...
From $457 per night (USD)VRBO
From $434 per night (USD)Expedia
Best of the Berkshires & Hudson Valley
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Located in Canaan, NY, less than a mile from the Massachusetts border, this wonderful 1700s post and beam farmhouse has ...
From $434 per night (USD)Expedia
From $359 per night (USD)VRBO
Near Tanglewood: Historic Summer Retreat
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Newly-renovated Berkshire Hills home where rustic charm meets modern elegance. Ideal for families or groups. The open-st ...
From $359 per night (USD)VRBO
From $290 per night (USD)VRBO
Saltbox-style residence in the Berkshires
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Discover the allure of this enchanting Saltbox-style residence nestled in the picturesque town of Hillsdale, NY. With t ...
From $290 per night (USD)VRBO
From $931 per night (USD)VRBO
Newly renovated private 3 bedroom house on a dead end road.13 acres & 360 views
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to your dream upstate country escape! This newly remodeled 3-bedroom, 3-bathroom home offers a perfect blend of ...
From $931 per night (USD)VRBO
From $693 per night (USD)VRBO
Hilltop: Panoramic Views w\/ Pool near Catamount
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: With 360-degree views of the Catskill and Berkshire Mountains from the highest point in Hillsdale, Hilltop is a ...
From $693 per night (USD)VRBO
From $640 per night (USD)VRBO
Silver Ridge: Hilltop Chalet w\/ Sweeping Views
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Perched high on the hills above Hillsdale, Silver Ridge is a perfectly-sited contemporary mountain lodge offeri ...
From $640 per night (USD)VRBO
From $2015 per night (USD)VRBO
***Your Own B&B*** Su
- Bedrooms:
- 13
- Bathrooms:
- 13
- Sleeps:
- 36
Summary: **Please message us prior to booking and talking with your group to confirm pricing and availability** Interio ...
From $2015 per night (USD)VRBO
From $332 per night (USD)VRBO
Cozy Log Cabin Retreat with Pool on 4 Acres
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Gather at the log cabin in the woods and enjoy the private pool (Memorial Day - Sept). Updated with all the essentials l ...
From $332 per night (USD)VRBO
From $183 per night (USD)VRBO
Berkshires 4br\/2ba, FALL, WINTER SKI JIMINY PK OR Long Term '25
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
BERKSHIRES - 4 BR/2BA - CHARMING, BEAUTIFULLY DECORATED (CHECK PHOTOS PLEASE) 1,800 sq. ft New England "farmhouse,'" 4 b ...
From $183 per night (USD)VRBO
From $402 per night (USD)VRBO
Superb Views -- Sunsets, Mountains, Valley
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Overview of availability in 2025 (as of 11/5/2024) : May 24-30 June 3-15 July 13 - August 17 Septe ...
From $402 per night (USD)VRBO
From $717 per night (USD)VRBO
Berkshires Year-Round Home-Great mountain & lake views, sunsets, close to Lenox
- Bedrooms:
- 4
- Bathrooms:
- 10
- Sleeps:
- 10
NEWLY RENOVATED This house has some of the most amazing views in the Berkshires, looking west over Queechy Lake; incred ...
From $717 per night (USD)VRBO
From $200 per night (USD)VRBO
Beautifully decorated & immaculate log chalet on 3 acres, winter views.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Private and secluded log cabin chalet is situated on three picturesque acres overlooking tall pines and forests with he ...
From $200 per night (USD)VRBO
From $242 per night (USD)VRBO
Two Rooms with En-Suite in Quiet Woodland
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Located in the heart of the Berkshires, midway between NYC and Boston, this newly renovated two bedroom apartment is nes ...
From $242 per night (USD)VRBO
From $1242 per night (USD)VRBO
Spectacular Private Hilltop Contemporary Estate (Pool\/Catamount\/Bash Bish Fall)
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 10
This fully renovated contemporary estate has it all to make it your place to escape all year round. Sitting on 11 pri ...
From $1242 per night (USD)VRBO
From $274 per night (USD)VRBO
Beautiful 3BR river view, huge glass wall Log House -2200 sq\/ft
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Sunny, specious log house on the river. The home has beautiful forest and river views through huge glass wall which is f ...
From $274 per night (USD)VRBO
From $116 per night (USD)VRBO
Getaway Near Mass MoCA, Great Hiking, Scenic Views
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 2
With almost seven years of hosting experience and 200+ great reviews through other platforms, you can't go wrong with ou ...
From $116 per night (USD)VRBO
From $330 per night (USD)VRBO
Modern Farmhouse near hiking, bike path & swimming
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Location - A 5 minute walk from the entrance of Taconic State park, our home is set on a tree lined acre in the hamlet ...
From $330 per night (USD)VRBO
Click For PricingVRBO
Summer rental 4Br - Big views + Pond, 10 acres bwtn Hudson and Great Barrington
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
In the foothills of the Berkshire Mountains on a quiet country road halfway between Great Barrington (15Min) and Hudson ...
Click For PricingVRBO
From $353 per night (USD)Expedia
Hudson valley and The Berkshires Cottage
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Summary: Welcome to your luxury cottage escape. Located in the heart of the Hudson Valley in Hillsdale, NY sits a calm, ...
From $353 per night (USD)Expedia
From $486 per night (USD)VRBO
Hudson Valley and The Berkshires getaway
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
Summary: Welcome to the Hudson Valley getaway. Located in the heart of the Hudson Valley in Hillsdale NY, sits our 4 be ...
From $486 per night (USD)VRBO
From $455 per night (USD)VRBO
Canaan Valley Home, A Berkshires Getaway
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 6
Views and authentic charm. Built in 1825, this 4-Bedroom, 2.5 Bath home is ideally located in the heart of Canaan Valley ...
From $455 per night (USD)VRBO
From $1676 per night (USD)VRBO
Stone Villa: 20 minutes to Tanglewood
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 10
This property is like nothing you've ever seen. After 2 years of renovation, we welcome you to the Stone Manor --a 150-y ...
From $1676 per night (USD)VRBO
From $358 per night (USD)VRBO
Caretaker's Cottage: 20 minutes to Tanglewood
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
This property is like nothing you've ever seen--a gem near the top of Mt. Lebanon with 86-acres of forest, streams, wate ...
From $358 per night (USD)VRBO
From $678 per night (USD)VRBO
BEAUTIFUL 4-SEASON RENTAL DIRECTLY ON TWIN LAKES
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
The Lodge sits prominently on our large property which used to be a children's summer camp. As such, we have tennis cour ...
From $678 per night (USD)VRBO
From $426 per night (USD)Expedia
Lovely Secluded Vermont Home: Stocked Pond, Trails, Ski.5 Mins to Williamstown!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
The Cottage At Mountain Meadow Originally built as a guest house on a 45 acre country estate in Vermont just five minute ...
From $426 per night (USD)Expedia
From $393 per night (USD)VRBO
Fickle Fox Farm. Leaf Peepers and Skiers! This is your season.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 11
Newly renovated three bedroom, two and half bath home on 6 bucolic acres in Canaan Valley, CT. Spend lazy summer days i ...
From $393 per night (USD)VRBO
From $253 per night (USD)Expedia
Experience the Beauty of the Berkshires and Hudson Valley in Our Historic Home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Escape to the Berkshires and step back in time with a stay in our charming historic home, conveniently located near the ...
From $253 per night (USD)Expedia