Berkshire Area Rentals
From $460 per night (USD)VRBO
CABIN FEVER IN STOCKBRIDGE
- Bedrooms:
- 2
- Bathrooms:
- 3
- 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 $460 per night (USD)VRBO
From $327 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 $327 per night (USD)VRBO
From $1040 per night (USD)VRBO
Thanksgiving in the Berkshires anyone? Fabulous Log Cabin perfect family getaway
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Stunning log cabin in The Berkshires on 10 wooded acres complete with brand new 4 season hot tub, pickleball court, fire ...
From $1040 per night (USD)VRBO
From $828 per night (USD)VRBO
In-Town Victorian 5 Bd Front House &\/or 6 Bd Back House w\/Beach Rights, Skiing
- Bedrooms:
- 8
- Bathrooms:
- 12
- Sleeps:
- 24
The Front 5 Bedroom Norman Rockwell Feel Home offers a Living Room, Den, Fully Stocked Kitchen, lovely screened porch & ...
From $828 per night (USD)VRBO
From $331 per night (USD)VRBO
Mounatin Getaway in the Heart of the Berkshires!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Welcome to the Lynne Court Guesthouse in the heart of the Berkshires! We are happy to share our gorgeous, nature-surrou ...
From $331 per night (USD)VRBO
From $251 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 $251 per night (USD)VRBO
From $289 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 $289 per night (USD)VRBO
From $234 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 $234 per night (USD)VRBO
From $597 per night (USD)VRBO
Sophisticated Lenox Retreat by Evergreen Home
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This beautiful Dutch Gambrel is the ideal spot for your next New England getaway. So spacious- with 4 bedrooms, 2.5 ba ...
From $597 per night (USD)VRBO
From $1269 per night (USD)VRBO
Luxury Berkshires Retreat in Lenox - Main House & Studio
- Bedrooms:
- 5
- 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 $1269 per night (USD)VRBO
From $864 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 $864 per night (USD)VRBO
From $443 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 $443 per night (USD)VRBO
From $173 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 $173 per night (USD)VRBO
From $228 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 $228 per night (USD)VRBO
From $213 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 $213 per night (USD)VRBO
From $527 per night (USD)VRBO
Private Woodland Getaway minutes from Ski Butternut
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Set in the heart of fifteen peaceful wooded acres and fronted by a private meadow, this beautiful chalet-style home with ...
From $527 per night (USD)VRBO
From $361 per night (USD)VRBO
Modern Berkshires Cottage 🌲 Gas Stove, Large Deck & W\/D + 7 mins to Otis Ridge
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to our brand new cottage, which is nestled in one of the Berkshires’ best areas for skiing, hiking, and spending ...
From $361 per night (USD)VRBO
From $289 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 $289 per night (USD)VRBO
From $472 per night (USD)VRBO
Berkshires family fun at Beautiful Hygge House on Richmond Pond- New Deck 2024!
- 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 $1583 per night (USD)VRBO
Morning Face - Berkshire estate with heated pool, views and privacy.
- Bedrooms:
- 5
- Bathrooms:
- 4
- Sleeps:
- 10
Morning Face is a meticulously restored Italian villa with privacy and mature gardens. Set on 20 acres, the beautifully ...
From $1583 per night (USD)VRBO
From $192 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 $192 per night (USD)VRBO
From $353 per night (USD)Expedia
Little House in the Woods by Evergreen Home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Fresh, cozy & serene, the Little House is set back from the road with several acres of woods behind & a wildlife preserv ...
From $353 per night (USD)Expedia
From $493 per night (USD)VRBO
Modern Cottage in the heart of the Berkshires with new exterior flex space!
- Bedrooms:
- 3
- 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 $493 per night (USD)VRBO
From $592 per night (USD)Expedia
Antique Farmhouse Totally Restored
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 16
This rambling farmhouse has a balanced mix of meticulous restoration with an eccentric flair. Undermountain Farm is a ho ...
From $592 per night (USD)Expedia
From $342 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 $342 per night (USD)VRBO
From $417 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 $417 per night (USD)Expedia
From $560 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 $560 per night (USD)VRBO
From $940 per night (USD)VRBO
Private Estate: 5 Bedrooms, Hot Tub, Tranquil Mood
- Bedrooms:
- 5
- 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 $940 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 $745 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 $745 per night (USD)VRBO
From $441 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 $441 per night (USD)VRBO
From $342 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 $342 per night (USD)VRBO
From $304 per night (USD)VRBO
Shingle style, Timber Frame, Berkshire Cottage beside babbling brook
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Colesbrook Manor is a timber frame, shingle-style cottage. A true retreat destination in and of itself anytime of the ye ...
From $304 per night (USD)VRBO
From $244 per night (USD)VRBO
Recently Renovated, steps to Lake Buel, close to Great Barrington & Stockbridge
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
This charming and appropriately named "Little Cottage" was newly renovated in 2017. Enjoy a short walk (300 feet) down ...
From $244 per night (USD)VRBO
From $383 per night (USD)VRBO
Spacious Comfortable Charming Family Farmhouse Great Location
- Bedrooms:
- 2
- Bathrooms:
- 4
- 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 $1020 per night (USD)VRBO
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 $1020 per night (USD)VRBO
From $186 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 $186 per night (USD)VRBO
From $190 per night (USD)VRBO
Cozy rustic cottage minutes away from Tanglewood and Stockbridge center
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 4
Beautiful small private cottage, across the road from Stockbridge Bowl Lake. Easy access ( 1 mile ) to Tanglewood, Very ...
From $190 per night (USD)VRBO
From $357 per night (USD)VRBO
Peaceful Woodland Home in the Heart of the Berkshires
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
The Residence is a beautiful, secluded home in the Berkshire foothills. The 14-acre property includes hiking trails thro ...
From $357 per night (USD)VRBO
From $239 per night (USD)VRBO
Comfortable, renovated 2 bedroom apartment in historic grist mill.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Renovated 2 bedroom (1 queen, 1 full) 2 bath 2nd floor apartment (stairs). Small kitchen w/refrigerator, 2 burner hotpla ...
From $239 per night (USD)VRBO
From $774 per night (USD)VRBO
Stunning Berkshire custom luxury home in private wooded community- walk to lake
- Bedrooms:
- 5
- 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 $774 per night (USD)VRBO
From $463 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 $463 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 $684 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 close to skiing, hiking, restaurants, Tanglewood and everything the Berkshires ...
From $684 per night (USD)VRBO
From $262 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 $262 per night (USD)VRBO
From $302 per night (USD)VRBO
Fall\/Winter 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:
- 4
- Bathrooms:
- 8
- 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 $309 per night (USD)VRBO
Idyllic Berkshire Get Away: Balance of relaxation and convenience
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
A charming 3-bedroom contemporary on one-acre property in lovely residential area of Great Barrington. The house has a s ...
From $309 per night (USD)VRBO
From $229 per night (USD)VRBO
Peaceful, Post and Beam Loft, Sleeps 9
- Bedrooms:
- 2
- Bathrooms:
- 2
- 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 $229 per night (USD)VRBO
From $727 per night (USD)VRBO
Lake House In The Heart Of The Berkshires
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Enjoy a beautiful, serene getaway nestled in the heart of the Berkshires. Waking up steps to a clean, clear, spring fed ...
From $727 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 $306 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 $306 per night (USD)VRBO
From $255 per night (USD)VRBO
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 $255 per night (USD)VRBO
From $294 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 $294 per night (USD)VRBO
From $784 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 $784 per night (USD)VRBO
From $260 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 $260 per night (USD)VRBO
From $271 per night (USD)VRBO
Serene, Private Waterfront House --Perfect Summer Retreat!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Enjoy everything the Berkshires has to offer from this beautiful, secluded, nicely renovated waterfront house set on two ...
From $271 per night (USD)VRBO
From $750 per night (USD)VRBO
Classic Antique Berkshire Farmhouse with heated pool and modern amenities.
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 11
Our antique farmhouse is minutes from town, hiking, and swimming. The large fenced in yard has a private pool, treehouse ...
From $750 per night (USD)VRBO
From $230 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 $230 per night (USD)VRBO
From $775 per night (USD)VRBO
Wyndham Bentley Brook - Jiminy Peak ski in\/out
- 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 $775 per night (USD)VRBO
From $636 per night (USD)VRBO
Picture-perfect farmhouse nestled in Berkshire County, MA near Tanglewood
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 9
Exquisitely renovated and tastefully appointed farmhouse getaway set high in the picturesque Tyringham Valley with acces ...
From $636 per night (USD)VRBO
From $909 per night (USD)VRBO
6BR Berkshire Bliss - 38 Acres of nature - minutes from Jiminy Peak Ski Resort
- Bedrooms:
- 5
- 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 $909 per night (USD)VRBO
From $530 per night (USD)VRBO
In the heart of the Berkshires
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
This meticulously cared for home is just ideal for year-round or vacation living. Enjoy the private screen porch on sum ...
From $530 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 $278 per night (USD)VRBO
Spacious Victorian duplex near MASSMoCA, MCLA (19)
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
This gorgeous late 19th century Victorian duplex recently under went a complete renovation. Situated on a lovely quiet s ...
From $278 per night (USD)VRBO
From $557 per night (USD)VRBO
Mountain View Retreat w\/ Hot Tub by Evergreen Home
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 7
Exceptional VIEWS!! Take in the sunrise sipping coffee on the front porch & the sunset in the evening while relaxing on ...
From $557 per night (USD)VRBO
From $977 per night (USD)VRBO
4 Bedroom House in the Berkshires. Minutes to all that the Berkshires offer!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 9
Enjoy the bucolic Berkshires. Nestled at the foot of Monument Mountain on a private road, you will 'chill' with your fa ...
From $977 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 $653 per night (USD)VRBO
Elegant & private light-filled 1 level, available June 5th thru July 5th
- Bedrooms:
- 3
- 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 $653 per night (USD)VRBO
From $330 per night (USD)VRBO
Vacation or work away from home! Private Beach Lakefront Cottage in Lenox MA
- Bedrooms:
- 2
- 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 $330 per night (USD)VRBO
From $521 per night (USD)VRBO
Richmond Pond Beauty
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
*4.8 Star Winter Wonderland in the heart of the Berkshires. Close to skiing, ice skating, tubing, hiking, etc. Ice fish ...
From $521 per night (USD)VRBO
From $306 per night (USD)VRBO
Huge Beautiful House-2 families-16 Acres -Low rates- 2 min from Jiminy Peak
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
2 MIN TO JIMINY PEAK - right down the road! Close to Lenox and Williamstown! Reduced rates. Great for 2 families (max 8 ...
From $306 per night (USD)VRBO
From $466 per night (USD)VRBO
5 BD, 3 Baths, sleeps 12 - the pool is open & a few openings for Summer 2024 !
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 12
NOTE: Our street name has changed to Woodland Hill (from Squaw Peak). Same house, same house number - different street ...
From $466 per night (USD)VRBO
From $334 per night (USD)VRBO
Beautiful Waterfront home with deep water dock on Onota Lake
- Bedrooms:
- 2
- Bathrooms:
- 5
- 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 $334 per night (USD)VRBO
From $551 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 $551 per night (USD)VRBO
From $524 per night (USD)VRBO
Great Barrington, Cabin Sleeps 14, Walk To Town
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 14
Summary: You and your family cannot beat this PRIME location in downtown Great Barrington while still feeling remote and ...
From $524 per night (USD)VRBO
From $817 per night (USD)VRBO
Gorgeous Sheffield Home in Heart of Berkshires
- Bedrooms:
- 4
- 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 $817 per night (USD)VRBO
From $332 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 $332 per night (USD)VRBO
From $343 per night (USD)VRBO
Simply Elegant Log Home Only 3 Minutes From Butternut! Recently renovated!
- Bedrooms:
- 3
- Bathrooms:
- 6
- 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 $343 per night (USD)VRBO
From $303 per night (USD)VRBO
Serene Berkshire Artist's House
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Beautiful, comfortable artist's house, that is tastefully furnished. Located on a very quiet 5 acre property abutting Mt ...
From $303 per night (USD)VRBO
From $203 per night (USD)VRBO
Monthly\/Yearly, All Season Vacation Rental, Minutes from Jimney Peak, MA
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Fully funished charming openspace house with kitchen dining and living areas, modern wood stove , contemporary master b ...
From $203 per night (USD)VRBO
From $707 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 $707 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 $432 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 $432 per night (USD)VRBO
From $204 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 $204 per night (USD)VRBO
From $558 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 $558 per night (USD)VRBO
From $407 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 $407 per night (USD)VRBO
From $212 per night (USD)VRBO
East Otis, MA, Waterfront Summer Cottage, Big Pond,
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Rental is weekly: Sunday to Sunday. This charming waterfront cottage is located on the pristine 333 acre lake known as B ...
From $212 per night (USD)VRBO
From $218 per night (USD)VRBO
Lakefront Cottage In The Berkshires In Western Massachusetts
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 4
INSIDE 650-square foot charming cottage directly on 129-acre Center Pond in Becket, MA. One main bedroom upstairs with q ...
From $218 per night (USD)VRBO
From $342 per night (USD)VRBO
Sprawling Berkshires Ranch Nestled In A Private Wooded Lot With Expansive Yards!
- Bedrooms:
- 4
- 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 $342 per night (USD)VRBO
From $810 per night (USD)VRBO
Huge Luxe Williamstown Updated Victorian, All Ensuite Baths, Walk to Spring St!
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 10
Feel at home in Williamstown in this Williams College legend! After housing generations of Williams students, Jake House ...
From $810 per night (USD)VRBO
From $773 per night (USD)VRBO
Custom Home In Scenic Wooded Area near small lake, Sleeps up to 16
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 16
The House - Set privately within the heart of the Berkshires, this sky lit, bright and immaculate year round home, will ...
From $773 per night (USD)VRBO
From $798 per night (USD)VRBO
Wyndham Bentley Brook Condo Resort
- 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 $798 per night (USD)VRBO
From $978 per night (USD)VRBO
Gracious Williamstown Home with Pool
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 8
This lovely home is located less than two miles from the Williams campus and has been fully updated, maintaining the bea ...
From $978 per night (USD)VRBO
From $138 per night (USD)VRBO
A-Frame in Sherwood Forest
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Come experience this gem of an A-frame. Situated on 1/2 acre wooded lot with no immediate neighbors on 3 sides. You can ...
From $138 per night (USD)VRBO
From $415 per night (USD)VRBO
Family vacation home in Great Barrington
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Spacious house in excellent condition on 3 secluded acres in Great Barrington, the heart of the Southern Berkshires, ava ...
From $415 per night (USD)VRBO
From $254 per night (USD)VRBO
Charming Cottage, New Marlborough Village Green in the Berkshires
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
The Cottage apartment is located in the Village of New Marlborough, Ma. We are on the Village Green. Across the road fro ...
From $254 per night (USD)VRBO
From $774 per night (USD)Expedia
Jaw dropping mountain & lake views in this stylish mountain home….
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 9
Curl up with a good book by the fire and gaze out at the dreamy picturesque mountain and lake views..... Or ski, swim, h ...
From $774 per night (USD)Expedia
From $394 per night (USD)VRBO
Stockbridge renovated classic- picture perfect
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Enjoy stylish and casual comfort in the perfect location to experience everything the Berkshires have to offer from this ...
From $394 per night (USD)VRBO
From $367 per night (USD)VRBO
Farmhouse with views nestled among nature reserve
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
This preserved 18th century farmhouse is situated on a picturesque 24 acre estate boasting southerly views of rolling hi ...
From $367 per night (USD)VRBO