The Berkshires vacation rentals

Search among available vacation rentals in The Berkshires from 50+ providers

Destination
Where do you want to go?
Check-in
Select date
-
Check-out
Select date
Rooms and Guests2 Guests, 1 Room
1Filter & Sort
View map
1-100 out of 145
8.8
Great22 reviews
4 adults
1 bedroom
2 beds
Situated less than 15 minutes' drive from Kirvin Park, this inn features a heated swimming pool, barbecue and entertainment activities.
FromUS$ 205 /nightSelect
8.0
Great61 reviews
4 adults
1 bedroom
1 bed
Set about 2.7 miles from National Shrine of the Divine Mercy, the pet-friendly Econo Lodge Lee - Great Barrington Lee boasts various recreational opportunities and entertainment activities available on site.
FromUS$ 52 /nightSelect
8.8
Great194 reviews
8 adults
1 bedroom
3 beds
Situated a 30-minute drive to Chesterfield Gorge, this villa features balcony and a terrace.
FromUS$ 150 /nightSelect
9.6
Perfect1 review
7 adults
3 bedrooms
4 beds
C.M. Gardner State Park is 2.9 miles from the perfect Historic Huntington Home - Walk To Westfield River.
FromUS$ 176 /nightSelect
BlantyreCountry house
8.8
Great25 reviews
2 adults
Located 2 miles from First Lenox Library, this hotel features an outdoor pool.
FromUS$ 1 337 /nightSelect
Featuring 18 rooms with views of the mountain, the Lodge @ America'S Switzerland North Adams is set about a 10-minute drive from MASS MoCA.
FromUS$ 181 /nightSelect
FromUS$ 212 /nightSelect
Ramblewild Adventure Park is within a 5-minute drive of the Mountain View Suite Sleeps 4 Ski Onoff Jiminy Peak, while Ioka Valley Farm is 1 miles away.
FromUS$ 204 /nightSelect
FromUS$ 169 /nightSelect
FromUS$ 279 /nightSelect
Located about 1.7 miles from Brodie Mountain, the Gorgeous New Zen Suite Sleeps 4-Ski On Off Jiminy Hancock boasts the outdoor swimming pool.
FromUS$ 318 /nightSelect
FromUS$ 157 /nightSelect
6 adults
3 bedrooms
3 beds
Stevens Glen is 4.5 miles from this villa that offers 3 bedrooms along with a kitchen.
FromUS$ 701 /nightSelect
The Woodland Hills Modern Cottage Minutes From Downtown is set about 20 minutes by foot from Fountain Pond State Park and a 25-minute walk from River Walk.
FromUS$ 450 /nightSelect
10 adults
4 bedrooms
6 beds
Round Pond is 0.2 miles from the Lakefront Berkshires Retreat With Deck, Dock And Boat!, while Bard College at Simon's Rock is 2.9 miles away.
FromUS$ 339 /nightSelect
FromUS$ 297 /nightSelect
Boasting a private pool, the family Ski On Off 1Br Suite 1St Flr Sleeps 4 Jiminy Peak Hancock is set a mere 5 minutes' walk from Jiminy Peak Mountain Resort.
FromUS$ 191 /nightSelect
Set 10 minutes' drive from Chesterwood Museum, the rooms in the Entire Home Hosted By Morgan Great Barrington have views of garden.
Select
The villa comes with 2 bathrooms and a full kitchen.
FromUS$ 287 /nightSelect
6 adults
2 bedrooms
3 beds
Situated 3 miles from Chesterwood Museum, the vacation home offers canoeing and fishing.
FromUS$ 442 /nightSelect
4 adults
1 bedroom
2 beds
Taft Farms is 6 miles from this villa that offers 1 bedrooms along with a fully equipped kitchen.
FromUS$ 189 /nightSelect
COZY GUESTHOUSE Minutes Away From Hiking!Apartment
Select
Casa Del BoscoVilla
Select
Your Stockbridge GetawayVilla
Select
Charming Apt In 18Th C Berkshire FarmhouseApartment
Select
Woodland Zen By Avantstay Modern Design PatioVilla
Select
The Entire Stephentown Hotel. 28 Person OccupancyVilla
Select
Berkshires Studio Apartment At The Stephentown HotelApartment
Select
2 Bed Berkshire Getaway Minutes To Jiminy Peak SkiApartment
Select
Linden By Avantstay Countryside Berkshire EscapeVilla
Select
Charming Barn In The Heart Of The BerkshiresApartment
Select
Cozy Mountain Cabin On Resort Property In Cultural BerkshireVilla
Select
Serene Berkshires Oasis With Pool And Sculpture GardenVilla
Select
Beautiful Berkshires Cottage On Lake BuelVilla
Select
Magical Country Retreat In The BerkshiresVilla
Select
Water Street ApartmentsApartment
Select
Monterey Home With Hot Tub, Pool And Game Room!Villa
Select
Great Barrington Getaway Lake Access, Water ViewsVilla
Select
Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone DecorApartment
Select
Hawley Home With Deck 4 Mi To Berkshire East ResortVilla
Select
Florida Mountain Log CabinChalet
FromUS$ 302 /nightSelect
Cozy Berkshires Cottage With 11 Private Acres!Villa
Select
Jiminy Peak Mountainside Getaway In The BerkshiresVilla
Select
Mountainside Condo @ Jiminy Peak In The BerkshiresVilla
Select
Private Berkshires Home On 5+ Acres Rustic & ChicVilla
Located within a 10-minute drive of Otis Poultry Farm, this villa includes 3 bedrooms.
Select
Berkshire Vacation Rentals: Private Cabin On Over 12 Acres Of WoodsVilla
Located within a 10-minute drive of Otis Poultry Farm, this villa includes 2 bedrooms.
Select
Berkshire Vacation Rentals: Pristine Home In Becket WoodsVilla
Located within a 10-minute drive of Becket Center Historic District, this villa includes 2 bedrooms.
Select
Berkshire Vacation Rentals: Private Estate Heated Yearround Outdoor PoolVilla
Located within a 5-minute drive of French Park, this villa includes 5 bedrooms.
Select
Berkshire Vacation Rentals: Beautiful Barn Style Home On Otis ReservoirVilla
Located within a 10-minute drive of Otis Reservoir, this villa includes 2 bedrooms.
Select
Berkshire Vacation Rentals: Centrally Located Historical HomeVilla
This is a 3-bedroom villa, set in proximity to Animagic Museum of Animation.
FromUS$ 339 /nightSelect
Berkshire Vacation Rental: Stockbridge Home Come Experience The BerkshiresVilla
Located within a 5-minute drive of Norman Rockwell Museum, this villa includes 2 bedrooms.
Select
Classic Stockbridge CottageVilla
Located within a 10-minute drive of Naumkeag, this villa includes 3 bedrooms.
Select
Berkshire Vacation Rentals: The Brookman: Renovated 6000 Sf Estate On 40 AcresVilla
Located within a 10-minute drive of Clark Art Museum, this villa includes 5 bedrooms.
Select
Berkshire Vacation Rentals: Renovated Five Bedrooms In Historic WilliamstownVilla
Located within a 10-minute drive of The Clark Art Institute, this villa includes 3 bedrooms.
Select
Berkshire Vacation Rentals: Peaceful Post And Beam Loft Sleeps 9Villa
Located within a 10-minute drive of Campbell Falls, this villa includes 2 bedrooms.
Select
Berkshire Vacation Rentals: Spacious & Serene Berkshires Retreat In The WoodsVilla
Located within a 5-minute drive of Chesterwood Museum, this villa includes 3 bedrooms.
Select
Berkshire Vacation Rentals: Loft Style Cabin In West Stockbridge Book NowVilla
Located within a 10-minute drive of Berkshire Botanical Garden, this villa includes 2 bedrooms.
Select
Berkshire Vacation Rentals: Great Barrington Walkable To Lake And TownVilla
Located within a 10-minute drive of East Mountain State Forest, this villa includes 2 bedrooms.
FromUS$ 399 /nightSelect
Berkshire Vacation Rentals: Great Barrington Cabin Sleeps 14 Walk To TownVilla
The villa is set near St. Peters Roman Catholic Church and has 3 bedrooms.
FromUS$ 822 /nightSelect
Beautiful House In The Woods Huge Yard Hot TubVilla
Located within a 15-minute drive of The Guthrie Center & Foundation, this villa includes 3 bedrooms.
FromUS$ 707 /nightSelect
Berkshire Vacation Rentals: Chic Pittsfield Home With A ViewVilla
Located within a 10-minute drive of Lake Onota, this villa includes 2 bedrooms.
Select
Magical Country Retreat In The BerkshiresVilla
FromUS$ 4 041 /nightSelect
Serene Monterey Home With Deck Near Skiing And Hiking!Villa
FromUS$ 389 /nightSelect
Wellspring By Avantstay Indoor Pool ViewsVilla
Guests can also enjoy access to The Mount, Edith Wharton's Home, which is 3.7 miles from the Wellspring by AvantStay Indoor Pool Views Richmond.
Select
A-Frame Cabin In Becket Deck And Private Acreage!Villa
Palmer Brook Reservoir is around 2.1 miles from the A-Frame Cabin In Becket Deck And Private Acreage!, while Becket Center Historic District is approximately 2 miles away.
Select
Spacious Tolland Home With Deck And Screened Porch!Villa
Granville State Forest H.Q is also set around 2.1 miles from the Spacious Tolland Home With Deck And Screened Porch!.
Select
Must See Pirate Suite Ski On Off Jiminy - Mtn View Fully Redone DecorApartment
Mountain Coaster is only 10 minutes by foot from the Must See Pirate Suite Ski On Off Jiminy - Mtn View Fully Redone Decor, while Brodie Mountain is around 1.7 miles away.
FromUS$ 279 /nightSelect
Pittsfield Home With Deck - 12 Mi To Jiminy Peak!Villa
While staying at the Home with Deck - 12 Mi to Jiminy Peak! you are invited to discover Berkshire Museum, set around a 15-minute drive away, or Herman Melville Memorial Room, which is 3.4 miles away.
Select
1St Floor Mountain View Suite Ski On Off At Jiminy- Fully Redone DecorApartment
Mountain Coaster is about 1.8 miles from the 1St Floor Mountain View Suite Ski On Off At Jiminy- Fully Redone Decor and Poppy Mountain is approximately 2.7 miles away.
FromUS$ 279 /nightSelect
Lake, Kayaks & Sauna - Family & WellnessChalet
The Amenity-Loaded, Lake Access, Kayaks & Ev-Charger is a perfect vacation spot 2.7 miles from Otis Ridge and other Otis landmarks.
Select
Cute Cape Cod Style HomeVilla
FromUS$ 165 /nightSelect
Tranquil Washington Home With Sauna, On 70 AcresVilla
Select
Cozy Becket Cottage Escape With Lake Access!Villa
Select
Monterey Haven Less Than Half Mi To Lake Garfield With KayaksVilla
FromUS$ 261 /nightSelect
Hawks Eye CabinVilla
FromUS$ 178 /nightSelect
Autumn Hill LakehouseVilla
Select
Country CharmerVilla
FromUS$ 306 /nightSelect
Cozy Berkshires Vacation Rental Near Hiking!Apartment
Select
Stockbridge Retreat With Pool And Hot Tub!Villa
Select
Pet-Friendly Tolland Cabin With Private Hot Tub!Villa
FromUS$ 208 /nightSelect
Getaway For A Weekend!Apartment
FromUS$ 175 /nightSelect
Lakefront Westhampton Cabin With Beach And Kayaks!Villa
Select
Berkshire Beauty-Full HomeVilla
Select
Massachusetts Vacation Rental With Deck And GrillVilla
Select
12-Acre Vacation Rental In The Berkshires!Villa
FromUS$ 241 /nightSelect
Hupi House - A Peaceful Wooded Lakeside RetreatVilla
Select
Serene Salisbury Rental Home On 26 Acres With Deck!Villa
Select
Winthrop Estate 12K Sf 32 AcresVilla
FromUS$ 3 265 /nightSelect
Downtown Great Barrington Enjoy Mountain ViewsVilla
FromUS$ 534 /nightSelect
Spacious Historic Home In The Berkshires!Villa
FromUS$ 289 /nightSelect
Built For A Us Secretary Of State 13K Sf In LenoxVilla
FromUS$ 1 982 /nightSelect
Historic Stockbridge On Main Street 3 BedroomApartment
FromUS$ 286 /nightSelect
Historic Two Bedroom Downtown StockbridgeApartment
FromUS$ 193 /nightSelect
New Luxury Lodge - 3 Fireplaces Mins To Ski & TownVilla
FromUS$ 765 /nightSelect
Vacation Rental Home In The Berkshires!Apartment
FromUS$ 149 /nightSelect
Luxury Vacation Rental In The Berkshires!Villa
FromUS$ 412 /nightSelect
Berkshires Getaway Less Than 1 Mi Skiing And Hiking!Apartment
FromUS$ 354 /nightSelect
Lakefront Otis Home With Stunning Views And Boats!Villa
FromUS$ 330 /nightSelect
Woodfall By Avantstay Tons Of Outdoor SpaceVilla
FromUS$ 633 /nightSelect
  • 1
  • 2

Vacation rentals in The Berkshires essential information

🏨 Vacation rentals in The Berkshires 145
👛 Lowest price 52 USD
✍️ Vacation rentals Reviews 303