Berkshire Area Rentals
From $661 per night (USD)VRBO
Hidden Oasis in the Mountains by Evergreen Home
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Escape with family & friends to this hidden oasis in the heart of the Berkshires. Enjoy the beautiful perennial garden ...
From $661 per night (USD)VRBO
From $606 per night (USD)VRBO
Hip Renovated Mid Century 4 Bedroom on Long Bow Lake
- Bedrooms:
- 1
- 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 $606 per night (USD)VRBO
From $150 per night (USD)VRBO
Vacation Village In The Berkshires 5 Star Resort - Suite B
- Bedrooms:
- 1
- Bathrooms:
- 1
- 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 $297 per night (USD)Expedia
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 $297 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:
- 1
- 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 $917 per night (USD)Expedia
Exclusive Estate, Heated Yearround Outdoor Pool
- Bedrooms:
- 4
- Bathrooms:
- 7
- Sleeps:
- 17
Summary: Awaiting your next trip in our former horse farm turned luxury vacation rental, recently upgraded and re-furnis ...
From $917 per night (USD)Expedia
From $410 per night (USD)VRBO
Beautiful, Private Berkshires Retreat w Magic View, 5min to Lake Garfield Beach
- Bedrooms:
- 1
- 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 $410 per night (USD)VRBO
From $326 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 $326 per night (USD)Expedia
From $489 per night (USD)VRBO
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)VRBO
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 $407 per night (USD)VRBO
Lenox Gem with AC! Super Rate for Aug 15 to 21!
- Bedrooms:
- 2
- 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 $407 per night (USD)VRBO
From $762 per night (USD)VRBO
11 acre mid-century estate, newly renovated, seasonally available pool.
- Bedrooms:
- 3
- 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 $762 per night (USD)VRBO
From $1117 per night (USD)VRBO
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 $1117 per night (USD)VRBO
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 $270 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 $270 per night (USD)VRBO
From $794 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 $794 per night (USD)VRBO
From $510 per night (USD)VRBO
Elegant 4 BR condo in Lenox, MA- completely new- 3 min from Tanglewood
- Bedrooms:
- 3
- 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 $524 per night (USD)VRBO
Mountainside: Large 3-level Jiminy Peak Home
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
From our easily accessible, newly renovated, fully equipped spacious home you can walk to the ski trails, hike and explo ...
From $524 per night (USD)VRBO
From $436 per night (USD)VRBO
CABIN FEVER IN STOCKBRIDGE
- Bedrooms:
- 1
- Bathrooms:
- 2
- 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 $436 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 $897 per night (USD)VRBO
Fabulous Renovated Log Cabin: the perfect getaway with new pickleball court!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Stunning log cabin in the Berkshires on 10 private wooded acres complete with brand new 4 season hot tub, in-ground pool ...
From $897 per night (USD)VRBO
From $987 per night (USD)VRBO
In-Town Victorian 5 Bd Front House &/or 6 Bd Back House w/Beach Rights, Skiing
- Bedrooms:
- 7
- Bathrooms:
- 12
- Sleeps:
- 24
The Front 5 Bedroom Norman Rockwell Feel Home offers a Living Room, Den, Fully Stocked Kitchen, lovely screened porch & ...
From $987 per night (USD)VRBO
From $175 per night (USD)VRBO
Available for Winter Rental, Healthcare, Central
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
If you are coming to the area to help in one of our Hospitals or Healthcare facility please contact us for booking optio ...
From $175 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
From $223 per night (USD)VRBO
Remote and Relaxing Cabin in the Berkshires
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Wake up to a beautiful view from this A-frame home built by our family. Unpack and unwind! Spend the day hiking(or snow ...
From $223 per night (USD)VRBO
From $551 per night (USD)Expedia
Sophisticated Lenox Retreat by Evergreen Home
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
This beautiful Dutch Gambrel is the ideal spot for your next New England getaway. So spacious- with four bedrooms, 2.5 ...
From $551 per night (USD)Expedia
From $247 per night (USD)VRBO
Charming cedar shingle cottage
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 7
A 3-bedroom lakefront cottage. Knotty pine interior with ample frontage on Big Pond. Dock available on property May - S ...
From $247 per night (USD)VRBO
From $1228 per night (USD)VRBO
Luxury Berkshires Retreat in Lenox - Main House & Studio
- Bedrooms:
- 4
- Bathrooms:
- 7
- Sleeps:
- 15
A private retreat in Berkshires set on 5 acres in prime location in Lenox - our all-season property offers secluded luxu ...
From $1228 per night (USD)VRBO
From $863 per night (USD)VRBO
Berkshires Home Makeover ~ Immaculate Lakefront Getaway ~ Dreamy Sunsets!
- Bedrooms:
- 6
- Bathrooms:
- 4
- Sleeps:
- 8
This 4 bedroom, 6 bath home takes advantage of its prime location on Laurel Lake, offering breathtaking waterfront views ...
From $863 per night (USD)VRBO
From $387 per night (USD)VRBO
Centrally Located Historical Home
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Summary: Come to enjoy views from this private, country escape. Decorated with many cool antiques and theatre related ob ...
From $387 per night (USD)VRBO
From $515 per night (USD)VRBO
Private Woodland Getaway minutes from Ski Butternut
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Set in the heart of fifteen peaceful wooded acres and fronted by a private meadow, this beautiful chalet-style home with ...
From $515 per night (USD)VRBO
From $352 per night (USD)Expedia
Modern Berkshires Cottage 🌲 Gas Stove, Large Deck & W/D + 7 mins to Otis Ridge
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Welcome to our brand new cottage, which is nestled in one of the Berkshires’ best areas for skiing, hiking, and spending ...
From $352 per night (USD)Expedia
From $304 per night (USD)VRBO
Equipped Villa with Access to Amazing Amenities!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Enjoy an awesome location and access to a number of exciting amenities including a fitness center, 2 pools, a hot tub, d ...
From $304 per night (USD)VRBO
From $648 per night (USD)VRBO
Home with Pool on 10 Acres
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Beautifully furnished, recently renovated Stockbridge home centrally located 3 miles from Tanglewood, 1 mile from Norman ...
From $648 per night (USD)VRBO
From $472 per night (USD)VRBO
Family Fun in The Berkshires at Beautiful Hygge House
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Thank you for checking out Hygge House on Richmond Pond! Hygge (hoo-ga) is the Danish art of enjoying life's simple ple ...
From $472 per night (USD)VRBO
From $1615 per night (USD)VRBO
Morning Face - Berkshire estate with heated pool, views and privacy.
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Morning Face is a meticulously restored Italian villa with privacy and mature gardens. Set on 20 acres, the beautifully ...
From $1615 per night (USD)VRBO
From $160 per night (USD)VRBO
Villa with Access to Various Amenities
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
When you stay in our villa, you'll have access to a number of exciting amenities including a fitness center, 2 pools, a ...
From $160 per night (USD)VRBO
From $211 per night (USD)VRBO
Spacious Villa with Access to Various Amenities!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
This is the perfect villa for your group! Enjoy an awesome location and access to a number of exciting amenities includi ...
From $211 per night (USD)VRBO
From $236 per night (USD)VRBO
Villa with Access to Amazing Amenities!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Sleeps 4 up to 6 people (Max 5 Adults) - Large and small outdoor pool - Two indoor pools: Open - Hot Tub - 2 on-site B ...
From $236 per night (USD)VRBO
From $396 per night (USD)VRBO
Spacious, Lake View Condo Near Tanglewood in the Heart of the Berkshires!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 14
This spacious, sunny condo at Foxhollow on the Lenox/Lee border is perfectly situated for you to enjoy the natural beaut ...
From $396 per night (USD)VRBO
From $531 per night (USD)VRBO
Modern Cottage in the heart of the Berkshires with new exterior flex space!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Drive down our private road to find an adorable and spacious cottage, nestled on four secluded wooded acres, with every ...
From $531 per night (USD)VRBO
From $595 per night (USD)Expedia
Antique Farmhouse Totally Restored
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 16
This rambling farmhouse has a balanced mix of meticulous restoration with an eccentric flair. Undermountain Farm is a ho ...
From $595 per night (USD)Expedia
From $382 per night (USD)VRBO
Little House in the Woods by Evergreen Home
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Inquire about long term! Fresh, cozy & serene, the Little House is set back from the road with several acres of woods be ...
From $382 per night (USD)VRBO
From $576 per night (USD)Expedia
Heart of Lenox!! - renovated downtown apartment
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Completely renovated 2-bedroom downtown apartment with open floor plan, located in the picturesque historical town of Le ...
From $576 per night (USD)Expedia
From $541 per night (USD)VRBO
Luxury Fox Hollow Estate Home on Laurel Lake - Dream Location, Hot Tub, Kayaks++
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 14
Newly Renovated for 2023 Cape Cod Style ,4BR, 4BA, sleeps 10-12. New fully equipped kitchen w/ center island, indoor an ...
From $541 per night (USD)VRBO
From $719 per night (USD)VRBO
Secluded Estate: Hot Tub, Walking Path To Downtown
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 16
Summary: Unparalleled views for miles and absolute killer location, built on Stone Hill Rd, which has a local walking pa ...
From $719 per night (USD)VRBO
From $150 per night (USD)VRBO
Vacation Village in the Berkshires 5 Star Resort - Suite A
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Gold Crown Resort! Spectacular mountain views, clubhouse, fitness center, indoor pool, outdoor jacuzzi, outdoor pool, ga ...
From $150 per night (USD)VRBO
From $466 per night (USD)Expedia
Minutes from downtown Great Barrington, Convenient location
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Built in 2015, this lovely 4 bedroom, 2500 sq.ft. home on a knoll is set back 175 feet from the street. This charming ...
From $466 per night (USD)Expedia
From $341 per night (USD)VRBO
Ashintully Cottage in spectacular setting
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 6
This bright cottage sits between Ashintully Gardens (landscaped public gardens with winding brook, fountain, paths and h ...
From $341 per night (USD)VRBO
From $190 per night (USD)VRBO
Relax, Read, Entertain, Or Walk To West Lake From Our Berkshire Home.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
2-bedroom, sun-filled, open floor plan that was recently renovated inside and out. Sits on lovely property with multipl ...
From $190 per night (USD)VRBO
From $383 per night (USD)VRBO
Spacious Comfortable Charming Family Farmhouse Great Location
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
ABOUT OUR PROPERTY: Experience a little of old New England. Our VRBO is a charming historic family farmhouse apartment( ...
From $383 per night (USD)VRBO
From $166 per night (USD)VRBO
East Otis, MA, Waterfront Summer Cottage, Big Pond,
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Rental is weekly; Sunday to Sunday This charming waterfront cottage is approximately 110 feet from the water. It is loca ...
From $166 per night (USD)VRBO
Click For PricingVRBO
A four-season forest cabin
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 8
This home is the perfect answer to fit your vacationing needs at any time of year. Ski, snowboard, snowshoe, or other o ...
Click For PricingVRBO
From $410 per night (USD)VRBO
Water front log cabin next to Tanglewood
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Log cabin in a very private setting on the water with a dock and access to the Stockbridge bowl. Waterfront property clo ...
From $410 per night (USD)VRBO
From $339 per night (USD)VRBO
Peaceful Woodland Home in the Heart of the Berkshires
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
The Residence is a beautiful, secluded home in the Berkshire foothills. The 14-acre property includes hiking trails thro ...
From $339 per night (USD)VRBO
From $1212 per night (USD)Expedia
5Bdrm/6Bath estate on Lenox - Stockbridge border, near BSO Tanglewood
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 20
Historic, elegant, recently renovated estate on 7 acres. BBQ grills outdoors. Near Jacob's Pillow Dance Festival, BSO ...
From $1212 per night (USD)Expedia
From $830 per night (USD)VRBO
Stunning Berkshire custom luxury home in private wooded community- walk to lake
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 4
*******Perfect Home for 1 to 12 People******* 5 BR's with 2 King Beds + 2 Queen Beds + 4 Twin Beds ...
From $830 per night (USD)VRBO
From $772 per night (USD)VRBO
Lovely vacation home on secluded hillside with views and heated pool
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Lovely home built into a 19th century barn placed on a secluded hill with gorgeous mountain views and a heated pool. The ...
From $772 per night (USD)VRBO
From $402 per night (USD)VRBO
Little Gem On Baldwin Hill In South Egremont
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Shingled farmhouse with modern interior. Spacious & sunny kitchen that connects to the large outdoor patio with fireplac ...
From $402 per night (USD)VRBO
From $267 per night (USD)VRBO
Quiet & private small horse farm only 1.5 miles to Jiminy Peak. Pet friendly.
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
The entire second floor of our horse barn is 1000+ square feet of cozy enjoyment, featuring a queen bed in the bedroom, ...
From $267 per night (USD)VRBO
From $302 per night (USD)VRBO
Spring/Summer Mountain Spa Nature Retreat with 15 Acre Trail System
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
This quiet ground floor residence located on 15 acres offers a modern rustic appeal. It includes a hot tub, dry sauna, a ...
From $302 per night (USD)VRBO
From $2286 per night (USD)VRBO
Iconic Cabin in the Berkshires
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 12
It’s hard to narrow down what is so special about this place. For each guest, it's likely something different. Maybe it’ ...
From $2286 per night (USD)VRBO
From $250 per night (USD)VRBO
Peaceful, Post and Beam Loft, Sleeps 9
- Bedrooms:
- 2
- Bathrooms:
- 1
- Sleeps:
- 9
Summary: Enjoy our lovely home for your next stay in the Berkshires! The list goes on but this house is the total packa ...
From $250 per night (USD)VRBO
From $620 per night (USD)VRBO
Renovated 1860's Farmhouse, across from the Miraval! Fenced in yard for dogs.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Ideally located just two minutes from the center of Lenox and across the street from the Miraval Resort and Spa. This e ...
From $620 per night (USD)VRBO
From $7446 per night (USD)VRBO
Charming Cabin On Scenic Road
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
One bedroom, one bathroom cottage on beautiful rural road. Wood burning stove and recently renovated kitchen makes it id ...
From $7446 per night (USD)VRBO
From $326 per night (USD)VRBO
Beautiful Mountainside House with nearby Lake and Hiking Trails
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Our secluded property is a great place to relax and enjoy the company of your friends and family. The house has all the ...
From $326 per night (USD)VRBO
From $670 per night (USD)VRBO
Lake Front Home in Heart of the Berkshires Near Jiminy Peak
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
Lakefront Home for Rent. Amazing location right on the water. In the summer the whole family can swim, kayak, paddleboa ...
From $670 per night (USD)VRBO
From $264 per night (USD)VRBO
Featured in a Home & Garden TV Special 30 South Mountain Road
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Comfortable, quiet home in Pittsfield minutes from Tanglewood, Berkshire Theater Festivals and other year round attracti ...
From $264 per night (USD)VRBO
From $308 per night (USD)VRBO
2200sf Secluded Family Mountain House 16 Acres- 2 min to Jiminy Peak- near Lenox
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
2 MIN TO JIMINY PEAK - right down the road and next door to RAMBLEWILD- #1 AERIAL ADVENTURE PARK IN THE BERKSHIRES! Clo ...
From $308 per night (USD)VRBO
From $532 per night (USD)VRBO
5 BD, 3 BA, sleeps 12. A few openings for Summer '25; booking thru Summer '26!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
NOTE: Our street name has changed to Woodland Hill (from Squaw Peak). Same house, same house number - different street ...
From $532 per night (USD)VRBO
From $375 per night (USD)VRBO
Beautiful Waterfront home with deep water dock on Onota Lake
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
Our 3 bedroom, 2 bath home has a huge 3 season sun room on the second floor with an even bigger covered deck below. The ...
From $375 per night (USD)VRBO
From $244 per night (USD)Expedia
Berkshire Lake access
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Our beautiful offshore lake house is walking distance to a private HOA beach. Bring friends or family to our four bedro ...
From $244 per night (USD)Expedia
From $200 per night (USD)VRBO
COZY LOFT w/ PRIVATE BEACH ON GORGEOUS MOUNTAIN LAKE IN THE BERKSHIRES
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 5
The LOFT is a unique private large 690 s.f. modern cabin like structure with great forest and garden views and access ...
From $200 per night (USD)VRBO
From $758 per night (USD)VRBO
Stunning Lakefront Berkshire Rental, Lake Garfield: private dock, boats, more
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 8
Get away from it all at our beautiful Berkshire lakefront wooded retreat. Swim, canoe, kayak, paddleboard, sunbat ...
From $758 per night (USD)VRBO
From $268 per night (USD)VRBO
In the Heart of Everything
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Lee Massachusettes! Located in the heart of the Berkshires, just 15 minutes to Tanglewood, 15 minutes to Jaco ...
From $268 per night (USD)VRBO
From $283 per night (USD)VRBO
Serene, Private Waterfront House --Perfect Summer Retreat!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Enjoy everything the Berkshires has to offer from this beautiful, secluded, nicely renovated waterfront house set on two ...
From $283 per night (USD)VRBO
From $168 per night (USD)VRBO
Hancock, MA: Studio w/Valley Views at All-Seasons Resort: Skiing, Hiking & More!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Complete your Berkshires retreat with a stay in the spacious Studios, perfect for romantic couples and small families. S ...
From $168 per night (USD)VRBO
From $550 per night (USD)VRBO
Wyndham Bentley Brook - Jiminy Peak ski in/out sleeps 8, 2 bedrooms 2 baths
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 8
Jiminy Peak Ski in/ski out in Winter. Summer activities at Jiminy Peak in the Berkshires. Fully equipped kitchen, living ...
From $550 per night (USD)VRBO
From $574 per night (USD)VRBO
Picture-perfect farmhouse nestled in Berkshire County, MA near Tanglewood
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 9
Tastefully appointed farmhouse getaway set high in the picturesque Tyringham Valley with access to a tennis/pickle ball ...
From $574 per night (USD)VRBO
From $887 per night (USD)VRBO
6BR Berkshire Bliss - 38 Acres of nature - minutes from Jiminy Peak Ski Resort
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 14
Our 6BR home is super comfortable, designed for multiple families to share (max 14 guests), up to date, and just minutes ...
From $887 per night (USD)VRBO
From $710 per night (USD)VRBO
In the heart of the Berkshires
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
This meticulously cared for home is just ideal for year-round or vacation living. Enjoy the private screen porch on sum ...
From $710 per night (USD)VRBO
From $291 per night (USD)Expedia
Becket Contemporary Cottage in the Woods Overlooking 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 $291 per night (USD)Expedia
From $283 per night (USD)VRBO
Spacious Victorian duplex near MASSMoCA, MCLA (19)
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
This gorgeous late 19th century Victorian duplex recently under went a complete renovation. Situated on a lovely quiet s ...
From $283 per night (USD)VRBO
From $472 per night (USD)VRBO
Restful pastoral, kids-friendly house w/ gardens, views, swimming pool, sauna
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Contemporary house in a beautiful pastoral setting. Viking stove, wood-burning fireplace, gunite heated saltwater pool, ...
From $472 per night (USD)VRBO
From $169 per night (USD)VRBO
Cozy and quaint country cottage, walk to downtown Williamstown
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to charming duplex in-law home in a family friendly neighborhood. This private and nicely decorated apartment, w ...
From $169 per night (USD)VRBO
From $523 per night (USD)VRBO
Elegant & private light-filled 1 level, available Sept. 1 - Oct. 31- disc. 20%
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
With soaring cathedral ceilings and light filled tranquility, off a quiet cul de sac road, this is the perfect place for ...
From $523 per night (USD)VRBO
From $341 per night (USD)VRBO
Vacation or work away from home! Private Beach Lakefront Cottage in Lenox MA
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Booking for the 2022 Fall Season. For more photos and information go to our website at www.lenoxmarental.com. Enjoy the ...
From $341 per night (USD)VRBO
From $281 per night (USD)VRBO
Simply Elegant Log Home Only 3 Minutes From Butternut! Recently renovated!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Comfortably sleeping 8 to 10 people, this sunny log cabin has a fireplace on each of its three levels, making it especia ...
From $281 per night (USD)VRBO
From $335 per night (USD)VRBO
Serene Berkshire Artist's House
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Beautiful, comfortable artist's house, that is tastefully furnished. Located on a very quiet 5 acre property abutting Mt ...
From $335 per night (USD)VRBO
From $574 per night (USD)VRBO
Great Barrington, Cabin Sleeps 14, Walk To Town
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 14
Summary: You and your family cannot beat this PRIME location in downtown Great Barrington while still feeling remote and ...
From $574 per night (USD)VRBO
From $558 per night (USD)VRBO
Renovated Downtown Great Barrington House
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Summary: Newly renovated three bedroom “on the hill” in Great Barrington awaits your next family stay. Short walk to dow ...
From $558 per night (USD)VRBO
From $717 per night (USD)VRBO
Tranquil Lake House Getaway on Onota Lake
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
Beautiful lake front house on 1.7 wooded acres on a very quiet end of Onota Lake. A long driveway takes you to this lo ...
From $717 per night (USD)VRBO
From $742 per night (USD)VRBO
Gorgeous Sheffield Home in Heart of Berkshires
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 15
Our home is a beautiful mountain-style home (exposed beams, wood floors, all new appliances) on a quiet rural road with ...
From $742 per night (USD)VRBO
From $276 per night (USD)VRBO
Beautiful Period Home in the Berkshires
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
Situated on 26 acres in the heart of the Berkshires in the small town of South Egremont, MA, this early 19th c. house co ...
From $276 per night (USD)VRBO
From $478 per night (USD)VRBO
Log style home 4 miles to Catamount with fitness room
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 7
In the summer spend time on the large screened porch and decks. Great room has sliding doors leading to deck facing eas ...
From $478 per night (USD)VRBO
From $210 per night (USD)VRBO
Cozy Modern Berkshires Rental (Mins from Lenox, Kripalu & Tanglewood)
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Come visit our brand new fully furnished cozy and modern vacation home in the Berkshires. This luxury home can sleep up ...
From $210 per night (USD)VRBO
From $593 per night (USD)VRBO
The best of both worlds, Country and Culture
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 8
5 bed rooms, 3 full baths, large kitchen with a prep pantry. Master bedroom on the 1st floor, another master on the 2nd ...
From $593 per night (USD)VRBO
From $340 per night (USD)VRBO
4 BR home w/ beautiful gardens on pond in Berkshires. Walking distance to town.
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
This house is close to Everything!! Tanglewood (3 miles), Kripalu (3 miles), theaters, Jacob's Pillow, Lee Outlets, etc ...
From $340 per night (USD)VRBO
From $185 per night (USD)VRBO
The Perfect Escape; Log Cabin situated on 40 Secluded Acres of Wilderness
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
https://www.partridgehillberkshires.com/ Under 3 hours from New York City and Boston, find yourself immersed in a four ...
From $185 per night (USD)VRBO
From $363 per night (USD)VRBO
Sprawling Berkshires Ranch Nestled In A Private Wooded Lot With Expansive Yards!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Come to the Berkshires and stay in one of the most beloved areas of Massachusetts. NOW WITH SUPER HIGH SPEED INTERNET ...
From $363 per night (USD)VRBO