Berkshire Area Rentals
From $274 per night (USD)VRBO
Fabulous Apartment - Great Barrington
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Five minutes from downtown Great Barrington, this apartment sits on 6 acres of open fields with a pond, running stream, ...
From $274 per night (USD)VRBO
From $648 per night (USD)Expedia
Canary Lodge - Berkshires Mountain Retreat - 6 Guests
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
This secluded mountaintop property sits on six acres in the very heart of the Berkshires. You will be at a three minute ...
From $648 per night (USD)Expedia
From $401 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 $401 per night (USD)VRBO
From $455 per night (USD)Expedia
Best of the Berkshires + Hot Tub by Evergreen Home
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Evergreen Home Vacation Rentals invites you to this stylish 2-bed, 1-bath cottage, just 10 minutes from Catamount and 7 ...
From $455 per night (USD)Expedia
From $419 per night (USD)VRBO
Wildlife Lakeside Cottage beautiful views, amazing wildlife, great location
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Light and bright defines the newly renovated cabin boasting spectacular wood throughout and freshly decorated rooms. Ra ...
From $419 per night (USD)VRBO
From $443 per night (USD)VRBO
Quiet & private small horse farm only 1.5 miles to Jiminy Peak. Dog 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 $443 per night (USD)VRBO
From $304 per night (USD)VRBO
Lovely ranch home getaway in The Berkshires- just 6 miles to Tanglewood
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This ranch home is in the heart of The Berkshires of Western Massachusetts, in the small town of Richmond. (West Stockbr ...
From $304 per night (USD)VRBO
From $762 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 $762 per night (USD)VRBO
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The Ponds at Foxhollow
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This smoke-free aparthotel features an indoor pool, an outdoor pool, and a fitness center. Free WiFi in public areas and ...
Click For PricingVRBO
From $558 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 $558 per night (USD)VRBO
From $257 per night (USD)VRBO
Peace and quiet on the lake
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
OPEN FOR ALL THE WONDERFUL SEASONS! You will love the peaceful and private lake and have plenty of other great things t ...
From $257 per night (USD)VRBO
From $422 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 $422 per night (USD)VRBO
From $856 per night (USD)VRBO
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Prior guests of this charming house next to the forest trails have already reserved their return stay for next year to e ...
From $856 per night (USD)VRBO
From $612 per night (USD)VRBO
Waterfront log cabin down a private dirt road next to Tanglewood
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Log cabin in a very private setting on the water with a dock and access to the Stockbridge bowl. Waterfront property clo ...
From $612 per night (USD)VRBO
From $430 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 $430 per night (USD)VRBO
From $524 per night (USD)Expedia
Walk to Dining: Downtown Lenox Guest House!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Steps to Main Street | 2 Mi to Tanglewood | Private Yard w/ Grill This Lenox vacation rental places you in the heart of ...
From $524 per night (USD)Expedia
From $608 per night (USD)VRBO
Wildlife Retreat in the Forest
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Home in the Birkshires! 12 minutes away from Jacob's Pillow, 2.5 hours away from NYC. Our Beautiful Lindal Cedar Contem ...
From $608 per night (USD)VRBO
From $471 per night (USD)Expedia
Berkshire Lake at the Pillow, and EV!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
At the intersection of New York. CT and MA, enjoy a newly finished Four Season Home with your own boat dock. Included 2 ...
From $471 per night (USD)Expedia
From $638 per night (USD)VRBO
Perfect Holiday Retreat, Completely Renovated, Central Location
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
Our completely renovated farmhouse is set upon a hilltop overlooking downtown Lee. It is a perfect spot for culture, sp ...
From $638 per night (USD)VRBO
From $449 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 $449 per night (USD)VRBO
From $283 per night (USD)VRBO
Steps to Lake Buel, close to Great Barrington & Stockbridge
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This charming and appropriately named "Little Cottage" was newly renovated in 2017. Enjoy a short walk (300 feet) down ...
From $283 per night (USD)VRBO
From $341 per night (USD)Expedia
The Meadows House @ Otis Ridge w/ 7-person hot tub
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Relax in a beautiful mountain setting at this 4-season ski house within walking distance of the slopes at Otis Ridge Ski ...
From $341 per night (USD)Expedia
From $594 per night (USD)VRBO
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 $594 per night (USD)VRBO
From $266 per night (USD)Expedia
Charming historic cottage on scenic road to Mt. Greylock
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
If you’ve driven by, you’ve wondered about the story of this beautiful stone building. Built in 1832 as a one-room scho ...
From $266 per night (USD)Expedia
From $787 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 p ...
From $787 per night (USD)VRBO
From $375 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 $375 per night (USD)VRBO
From $577 per night (USD)VRBO
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 $577 per night (USD)VRBO
From $656 per night (USD)Expedia
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, barbecue, ...
From $656 per night (USD)Expedia
From $549 per night (USD)VRBO
Enjoy a renovated private home right in downtown Lenox
- Bedrooms:
- 1
- 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 $549 per night (USD)VRBO
From $219 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 $219 per night (USD)VRBO
From $1308 per night (USD)VRBO
Stunning Post & Beam home minutes from Lenox, Stockbridge and Tanglewood!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 14
Bright and airy, cathedral ceiling, Post & Beam home situated in the heart of the Berkshires, minutes from Lenox, Tangle ...
From $1308 per night (USD)VRBO
From $861 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 $861 per night (USD)Expedia
From $446 per night (USD)VRBO
North Getaway Cottage
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
A great place for vacationers and those seeking a remote work or school location with three work areas and a guest print ...
From $446 per night (USD)VRBO
From $413 per night (USD)Expedia
Stockbridge Cape near Tanglewood & Kripalu - Heart of the Berkshires!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
Our home is nestled on 2.6 acres in the heart of the Berkshires! We are within 2 miles to Tanglewood & Kripalu while ju ...
From $413 per night (USD)Expedia
From $1307 per night (USD)VRBO
Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
In 2016 Smithsonian Magazine deemed Great Barrington, "The Best Small Town in America." Manor Lane is a private French C ...
From $1307 per night (USD)VRBO
From $670 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 $670 per night (USD)VRBO
From $723 per night (USD)VRBO
Spacious Lakeside Berkshire Home Close to Tanglewood and Jacob's Pillow
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 10
The lakeside house is built on a 1.1 acre lot with view of Lake Garfield. It is only a few minutes walk to the town's b ...
From $723 per night (USD)VRBO
From $410 per night (USD)VRBO
Seasonal Rental, Walk to slopes, sleeps 8 located at Jiminy Peak Resort
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Discounted seasonal rate available (December - March / June - September). Inquire for details. Let this newly renova ...
From $410 per night (USD)VRBO
From $751 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 $751 per night (USD)VRBO
From $391 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 $391 per night (USD)Expedia
From $201 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 $201 per night (USD)VRBO
From $580 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 $580 per night (USD)VRBO
From $1765 per night (USD)VRBO
Berkshires Retreat in Lenox - Main House & Studio
- Bedrooms:
- 4
- Bathrooms:
- 8
- Sleeps:
- 17
A private retreat in Berkshires set on 5 acres in prime location in Lenox - our all-season property offers secluded luxu ...
From $1765 per night (USD)VRBO
From $1354 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 $1354 per night (USD)VRBO
From $501 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 o ...
From $501 per night (USD)VRBO
From $366 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 $366 per night (USD)VRBO
From $310 per night (USD)VRBO
Cozy Cabin on Lake Mahkeenac
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Cozy cabin located in the popular Beachwood community which is 2 miles from Tanglewood on Stockbridge Bowl, close to Kr ...
From $310 per night (USD)VRBO
From $502 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 $502 per night (USD)VRBO
From $983 per night (USD)VRBO
Perfect location in the heart of downtown Lenox
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
If you want to feel like you're truly away, but still have access to a great lifestyle, this is the rental for you! St ...
From $983 per night (USD)VRBO
From $287 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 $287 per night (USD)VRBO
From $695 per night (USD)VRBO
Sophisticated Lenox Retreat by Evergreen Home
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Evergreen Home Vacation Rentals invites you to this beautiful Dutch Gambrel, the ideal base for your New England getaway ...
From $695 per night (USD)VRBO
From $260 per night (USD)Expedia
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Remember the simple pleasures of a country, lakeside vacation where you can spend the day swimming or boating, exploring ...
From $260 per night (USD)Expedia
From $362 per night (USD)VRBO
Main Street Delight 1bedroom
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Located on Main Street in downtown Lenox. A beautifully space fully equipped for all your needs. The eat-in kitchen has ...
From $362 per night (USD)VRBO
From $242 per night (USD)Expedia
Deluxe Redone Country Inn Suite at Jiminy-Sleeps 4 - Ski On/Off at Mountain Base
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: You want to pop out of bed, walk downstairs, and be right on the mountain - this is the place for you. This 1B ...
From $242 per night (USD)Expedia
From $992 per night (USD)VRBO
InTown Victorian Front House 5 Bd 3.5 Ba Back House 6 Bd 4 Ba Both 11 Bd 7.5 Ba
- Bedrooms:
- 7
- Bathrooms:
- 12
- Sleeps:
- 24
The Front 5 Bedroom 3.5 Baths Norman Rockwell Feel Home offers a Living Room, Den, Fully Stocked Kitchen, lovely screene ...
From $992 per night (USD)VRBO
From $557 per night (USD)Expedia
Berkshire's Best~On the Water~Mt. Views, Museums, Paddling, Hiking, Relaxing
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Windsor Cottage is a relaxing, lakeside retreat located on Windsor Lake in North Adams, MA where you will enjoy your own ...
From $557 per night (USD)Expedia
From $312 per night (USD)VRBO
Beachwood Cottage
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Unique small cottage in the sought-after Beachwood community situated 2 miles from Tanglewood on Stockbridge Bowl. Featu ...
From $312 per night (USD)VRBO
From $601 per night (USD)Expedia
Historic Stockbridge Villa on 25 acres
- Bedrooms:
- 6
- Bathrooms:
- 11
- Sleeps:
- 16
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 $601 per night (USD)Expedia
From $405 per night (USD)VRBO
Historic Charm, Modern Amenities: book this Berkshires retreat for family fun!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
<b>Your Cozy Berkshires Getaway Awaits!</b> Escape to the serene beauty of the Berkshires! Nestled in a peaceful, fami ...
From $405 per night (USD)VRBO
From $1150 per night (USD)Expedia
Fabulous Log Cabin: the perfect getaway with new pickleball court and pool!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Stunning log cabin in the Berkshires on 10 private wooded acres complete with brand new 4 season hot tub, in-ground pool ...
From $1150 per night (USD)Expedia
From $574 per night (USD)VRBO
Country Living just minutes from Everything! SKIERS! WE HAVE SNOW!!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
2 minutes to Bartlett's Apple Orchard, Richmond 5 minutes to Bousquet Ski Area, Pittsfield 6 minutes to Balderdash Cella ...
From $574 per night (USD)VRBO
From $1173 per night (USD)Expedia
The Great Escape Ski Cottage w/HOT TUB @ Great Barrington
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 16
Well appointed Vacation Cottage, newly renovated by the Owners; An Architect and an Interior Designer as a Modern Farmho ...
From $1173 per night (USD)Expedia
From $290 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 $290 per night (USD)VRBO
From $1077 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 $1077 per night (USD)VRBO
From $551 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 $551 per night (USD)VRBO
From $526 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 $526 per night (USD)VRBO
From $331 per night (USD)VRBO
Hearts Desire is your private escape.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Newly renovated, one level house with 2 rooms with king sized beds, 1 queen size sleeper sofa. Fully furnished kitchen ...
From $331 per night (USD)VRBO
From $883 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 $883 per night (USD)VRBO
From $417 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 $417 per night (USD)VRBO
From $723 per night (USD)Expedia
Stylish Mid-century Modern Berkshires Cape
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Stylish, fully renovated 4 bedroom, 2.5 bath home located in the heart of the Berkshires! Enjoy the large, sunny yard an ...
From $723 per night (USD)Expedia
From $400 per night (USD)VRBO
Little Longbow Lakefront Chalet
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
66 Long Bow Ln E is nestled within a quiet private community, offering guests a true escape into nature. The home sits ...
From $400 per night (USD)VRBO
From $631 per night (USD)Expedia
Elegant Pittsfield Home Near Downtown & Skiing!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Experience a fun-filled group getaway at this Pittsfield vacation rental! Named 'The Duchess of Pomeroy' for its charmin ...
From $631 per night (USD)Expedia
From $436 per night (USD)VRBO
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 $436 per night (USD)VRBO
From $287 per night (USD)Expedia
A Beautiful Log Cabin In The Woods, On Pontoosuc Lake, Yet Near Everything
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
Greetings from John at the American House! This is the perfect getaway to destress and relax! This is an original Lincol ...
From $287 per night (USD)Expedia
From $292 per night (USD)VRBO
SKI-IN, SKI-OUT! LIFT and MT. VIEWS UNBEATABLE LOCATION for ALL SEASONS! Unit 2
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 9
This ski-in, ski-out condo is located right at the base of the mountain in JJ’s Lodge in the heart of the village at Jim ...
From $292 per night (USD)VRBO
From $808 per night (USD)Expedia
Lake View Berkshires Retreat - Private & Minutes to Lenox
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 14
Start your day with lake views and the quiet pace of the Berkshires. Mornings here are easy and unhurried — enjoy a cup ...
From $808 per night (USD)Expedia
From $399 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 $399 per night (USD)VRBO
From $602 per night (USD)VRBO
Winterberry Lodge: NEWLY RENOVATED Spacious Berkshire Getaway at Jiminy Peak
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
FULLY RENOVATED FALL 2023. Beautiful Berkshire home with modern furnishings. This fabulous multi-level 3 bedroom house ...
From $602 per night (USD)VRBO
From $652 per night (USD)VRBO
Family-Friendly Hancock Home: Walk to Slopes!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 15
Situated in the town of Hancock, 'Whistling Birches' offers guests 4 bedrooms, 3 bathrooms, a prime location just steps ...
From $652 per night (USD)VRBO
From $211 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 $211 per night (USD)VRBO
From $175 per night (USD)VRBO
Elegant 19th Century New England Newly Renovated 1BR Vacation Rental
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Newly renovated unit with fireplace in main room, bathroom, bedroom (queen) and kitchenette.The unit also has a futon th ...
From $175 per night (USD)VRBO
From $1043 per night (USD)Expedia
Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!
- Bedrooms:
- 6
- Bathrooms:
- 7
- Sleeps:
- 15
This charming former tavern and stage coach inn makes the perfect four season getaway. You'll feel like you've taken ove ...
From $1043 per night (USD)Expedia
From $278 per night (USD)VRBO
2 Bedroom renovated townehouse, #5 , Beautifully decorated at Garfield House
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Garfield House Vacation living for short or longer stays in a newly renovated townhouse is in close proximity to all Ber ...
From $278 per night (USD)VRBO
From $380 per night (USD)Expedia
Cozy Home In The Berkshires, Pet Friendly with fenced in yard!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Come and enjoy the many adventures and activities that The Berkshires in Massachusetts has to offer. This cute 2 bedroo ...
From $380 per night (USD)Expedia
From $451 per night (USD)VRBO
Two Blocks from the Red Lion Inn & next to Berkshire Theater
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
My place is close to Stockbridge center, Berkshire Theaters, Great Barrington, Lenox, and the Berkshires in general - gr ...
From $451 per night (USD)VRBO
From $465 per night (USD)VRBO
Berkshires Getaway Walk to Distillery - No Pet Fee!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Hi! Welcome to the Berkshires! Enjoy total privacy on a full acre property overlooking 200 acres of conservation land. W ...
From $465 per night (USD)VRBO
From $389 per night (USD)VRBO
Spacious waterfront Berkshire home family private get-away
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This renovated waterfront home offers incredible views. Big Pond is surrounded by dense forests and abuts state park lan ...
From $389 per night (USD)VRBO
From $307 per night (USD)VRBO
Elegant 19th Century New England 2BR vacation rental at Garfield House
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
This super comfortable and spacious Berkshires getaway is located on Main St. in Lee, Massachusetts. The main level has ...
From $307 per night (USD)VRBO
From $576 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 $576 per night (USD)VRBO
From $510 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 $510 per night (USD)VRBO
From $265 per night (USD)VRBO
Two Bedroom house in the heart of the Berkshires
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Relax and enjoy the beauty of the Berkshires in this comfortable two-bedroom apartment. The apartment features two bedr ...
From $265 per night (USD)VRBO
From $549 per night (USD)Expedia
Picturesque Cottage with Sunroom on Ashmere Lake!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Dive into the rich culture, adventure, and beauty of the Berkshires with this Lake Ashmere vacation rental cottage! Insi ...
From $549 per night (USD)Expedia
From $607 per night (USD)VRBO
Sunset River Views, SIP, Spotless, Sleeps 8
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Conway House sits overlooking the sparkling Housatonic River, with vast views. This newly built (2021) contemporary chal ...
From $607 per night (USD)VRBO
From $324 per night (USD)Expedia
Renovated Downtown 1bedroom
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Located in the heart of historical downtown Lenox. A beautifully renovated space fully equipped for all your needs. The ...
From $324 per night (USD)Expedia
From $324 per night (USD)VRBO
Historical Downtown 1bedroom
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Located in the heart of historical downtown Lenox. A beautifully renovated space fully equipped for all your needs. The ...
From $324 per night (USD)VRBO
From $249 per night (USD)Expedia
Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Summary: This is the MOST UNIQUE suite in the Berkshires, specially designed for an incredible experience. The Master ...
From $249 per night (USD)Expedia
From $1368 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 $1368 per night (USD)VRBO
From $712 per night (USD)Expedia
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 $712 per night (USD)Expedia
From $703 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 $703 per night (USD)VRBO
From $711 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 $711 per night (USD)VRBO