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Vacation Rentals & Apartments in Berkshires

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128 apartments

Waterfront Cottage - 10 Mins to Great Barrington!

New Marlborough cottage

2 bedrooms / 1 bathroom / sleeps 4

Responds fast! avg. 5 minutes

Price per night from

$214

Great Vacation House in the Berkshires by Richmond Pond

Richmond house

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$216

Cozy Modern Condo for the Berkshires

West Stockbridge condo

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$294

3BR Lee House w/ Easy Access to Main Street!

Lee house

3 bedrooms / 2 bathrooms / sleeps 10

Responds fast! avg. 5 minutes

Price per night from

$227

Updated Jiminy Peak Condo w/ Patio & Pool Access!

Hancock apartment

2 bedrooms / 2 bathrooms / sleeps 10

Responds fast! avg. 5 minutes

Price per night from

$219

Enjoy horses and the largest recreational lake in Massachusetts

East Otis apartment

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$126

Big Beautiful 7 bedroom 3 bath hot tub pool table

Pittsfield house

7 bedrooms / 3 bathrooms / sleeps 18

Price per night from

$353

Spacious wooded home

Becket house

4 bedrooms / 6 bathrooms / sleeps 12

Price per night from

$230

Escape to the Berkshires!

Becket house

4 bedrooms / 3 bathrooms / sleeps 8

Responds fast! avg. 3 hours 4 minutes

Price per night from

$324

Rustic Berkshires Cottage at Lake Buel w/ Kayaks!

New Marlborough cottage

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 5 minutes

Price per night from

$131

New Timberframe House Rental in the Berkshire Mountains, Masschusetts

Hinsdale house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$164

Apartment walking distance to Mass MoCa!!

North Adams apartment

2 bedrooms / 1 bathroom / sleeps 10

Price per night from

$205

Christmas in The Berkshires

Hancock condo

1 bedroom / 2 bathrooms / sleeps 4

Price per night from

$265

Beautiful Lakefront Berkshire Rental

Monterey house

5 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$503

Shaker Hill

Great Barrington house

5 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$441

Lake House in Berkshires

North Adams cottage

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$124

Unique People & Pet-Welcoming Country Haven

Charlemont apartment

1 bedroom / 1 bathroom / sleeps 4

“Cozy little spot, kid and definitely dog friendly” We brought our Cavalier with us and had a great time at the cottage. It was clean and gave us tons of room. Would definitely stay again.

Price per night from

$161

Traditional Lenox Home, Walk to Downtown & Dining!

Lenox house

3 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 5 minutes

Price per night from

$220

Restored 1886 Eyebrow Colonial

Stockbridge house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$252

Comfortable Farmhouse in the Berkshires

West Stockbridge farmhouse

5 bedrooms / 3 bathrooms / sleeps 12

Responds fast! avg. 1 hour 34 minutes

Price per night from

$383

Lakefront Berkshires Ski/Summer House, Great Views

Great Barrington house

4 bedrooms / 2 bathrooms / sleeps 10

Price per night from

$216

Berkshires Waterfront Lakehouse Sanctuary

Lanesboro house

3 bedrooms / 2 bathrooms / sleeps 6

Responds fast! avg. 3 hours 34 minutes

Price per night from

$224

Spacious Lakeside Berkshire Home

Monterey house

4 bedrooms / 5 bathrooms / sleeps 10

Responds fast! avg. 3 hours 48 minutes

Price per night from

$514

Quiet Comfortable Cabin 5 Min. Walk to Lake

Becket house

2 bedrooms / 1 bathroom / sleeps 4

“Great winter getaway spot” My girlfriend and I spent new years at this awesome cabin tucked away in Becket, ma. It was quiet, clean, spacious and just about everything we could have asked for. The property was great, there was lots to do in nearby areas and we had a great time spending nights by the wood stove watching movies on their entertainment setup. I'd definitely recommend it for anyone looking to get out of the city for a few days to just relax and do something different!

Price per night from

$171

Designer Loft Style Residence

Sheffield house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$529

Berkshires: Romantic Cottage with spectacular view

Great Barrington cottage

1 bedroom / 1 bathroom / sleeps 3

“Perhaps the most relaxing vacation I've ever had” The Sigels' cottage was absolutely perfect for us. My husband and I were looking for a nice quiet 4-night stay while our 7-yr-old twins visited with their grandparents. When we arrived everything looked just as in the pictures. The room is sunny, but stays nice and cool too (we were there in august). There is an overhead fan but we didn't even need it. The Sigels made us feel very much at home, but they also seemed to know that we were not looking for a chatty B&B; experience. There are plenty of little touches like a bottle of wine waiting for us, tea, sugar, and some other basics in the kitchenette. A hair dryer, eye shade in the bedside table, etc. But nothing seemed overly fussy-- they are naturally good hosts. The pool was absolutely perfect. Big enough to swim laps, but small enough to be a nice temperature. We spent one whole morning just floating in the pool. The view from the pool is stunning. I am sure there are some amazing hikes around (I had broken my tailbone so hiking will have to wait for next year). Great Barrington is a wonderful town too, so if you're wondering where to stay in the Berkshires, then you would be wise to choose GB. It's not huge, but we never really left town. The walkable part of town has great diners, a cool little coffee shop, a movie theatre, used book store, and great music and food at the Gypsy Joynt (a member of the family that owns it-- Jordan Weller-- put out the best CD I've heard in a long time!) On our last night there the Sigels suggested we go to the Guthrie Center for an open mic where we heard more great music. I can't say enough about the Seigel's cottage. We can't wait to go back next summer.

Price per night from

$260

Gartner House, a charming home in Lenox

Lenox apartment

4 bedrooms / 1 bathroom / sleeps 7

“Great Location In Lenox” My family, friends, & I had a wonderful 2 weeks at Gartner House. It is within easy walking distance of nice shops, terrific restaurants, & a friendly library. Not far are Chesterwood, Tanglewood, Jacob's Pillow, Mass MoCa, Norman Rockwell, & a great, newly renovated Beshire Museum in Pittsfield.

Price per night from

$236

3 BR apartment, walking distance to Mass MoCa

North Adams apartment

3 bedrooms / 1 bathroom / sleeps 15

Price per night from

$218

Gem of the Berkshires, walk to downtown & lake.

Great Barrington house

5 bedrooms / 4 bathrooms / sleeps 12

“Wonderful Home!” We had a wonderful weekend! The home and area are lovely - easy walk to town for drinks and dinner - and enjoyed sitting on the many porches, looking out at the view. The home has been upgraded and the kitchen and living areas are beautiful. Thank you!

Price per night from

$344

Whitman Woods - A Berkshire Vacation

Hancock house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$116

House On Main Street

Williamstown house

4 bedrooms / 5 bathrooms / sleeps 16

Responds fast! avg. 1 hour 19 minutes

Price per night from

$1,117

RiverSong Suite In The Berkshires

North Egremont apartment

1 bedroom / 1 bathroom / sleeps 2

Responds fast! avg. 9 minutes

Price per night from

$223

Cozy & Modern Home -mins from Tanglewood & Kripalu

West Stockbridge apartment

2 bedrooms / 1 bathroom / sleeps 6

Price per night from

$113

BERKSHIRES RETREAT-LARGE 6+ BR HOME W/ AMENITIES

Otis house

6 bedrooms / 5 bathrooms / sleeps 14

Price per night from

$705

Retreat in the Woods

Savoy house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$230

To Ski or Not to Ski? Great conditions Great fireplace.Your Choice.

West Stockbridge house

3 bedrooms / 3 bathrooms / sleeps 8

“A memorable weekend getaway includes the most perfect house..” My husband and I had the pleasure to rent out this house last summer with another married couple and their son. Although our daughter and their son truly enjoyed Tanglewood and our visits into Town (which are both extremely close), I can't help but think that my favorite part of our vacation was the house we were staying in! The space felt both warm and welcoming and fit our group size perfectly. We also had access to a private quarry that the owners have rights to- bonus! I am quite disappointed that our summer dates are already booked.. but have already started to plan for this Fall.

Responds fast! avg. 1 hour 15 minutes

Price per night from

$402

Stone School Cottage

Lanesboro cottage

2 bedrooms / 1 bathroom / sleeps 5

“A wonderful experience” My parents really enjoyed their stay. They said everything was wonderful. It is a very charming and has wonderful history. They really thought the baby horses playing in the field across the street was an over the top touch.

Price per night from

$183

Fabulous Post & Beam Berkshire Rental

Monterey house

/ 2 bathrooms / sleeps 7

Price per night from

$211

Viewing 38 of 128
rentals in Berkshires

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About Berkshires

A Berkshires getaway in the Berkshire Mountains of Massachusetts is the perfect way to escape the bustle of everyday life and experience breathtaking natural beauty. Get the most out of your time here by staying in a vacation rental, such as a secluded cabin in the woods. Wake up in your vacation rental to the sound of birds and forest life, and enjoy coffee on your private balcony as the sun rises. Then wander downtown to explore the shops, local museums, and unique independent art galleries. In the afternoon, head for the trails to hike to cascading waterfalls, experience a Berkshires zip line adventure, or take an ATV tour. At the end of a busy day, retreat to your home away from home and host a barbeque or a game night for your family and friends.

Here are a few additional suggestions for your trip:

  • Go horseback riding: There are several well-maintained stables in the Berkshires area that offer lessons or guided single and multi-day trail rides.
  • Take a snowmobiling lesson: During the winter, the back country trails through the mountains are perfect for snowmobiling. Take a lesson or join a group adventure.
  • Go skiing or snowshoeing: Cross country skis offer a quieter way to explore the pristine snowy trails and increase opportunities to spot elusive wildlife like foxes and black bears.
  • Go fishing: Take a fly fishing trip along the winding, hidden waterways, or rent a boat and cast your line in the lake at sunrise.
  • Spend an afternoon in the spa: Indulge in a day of pampering at a Berkshires spa with a manicure, pedicure, or hot rock massage.
  • Play golf: Tee off at any one of several champion caliber, emerald green golf courses throughout the Berkshires region.

No matter what activities you have in mind for your vacation or what time of year you plan to visit the Berkshires, you'll find endless things to do here, and the best way to enjoy it all is with your own private vacation rental. Find a cabin or condo that offers all the luxury amenities you and your family need, then relax, unwind, and make great vacation memories. While you're in the Berkshires, you may also want to visit the coast and explore the historic villages of Cape Cod.

Top Destination reviews

Comfortable Farmhouse in the Berkshires
Great family accommodations in the Berkshires

We needed a house for our family of five, plus my brother, one daughter in law and a girl friend that provided space and privacy - for a summer weekend in the Berkshires. This property filled the bill admirably. It's a rambling farmhouse with lots of rooms, a well-appointed kitchen, and great outdoor space - perfect for our group. The location is very convenient as well, with easy access to all of the towns in Southern Berkshire County. The owners were responsive and very easy to deal with, they even left a nice welcome basket with local food items for us. Would definitely rent this property again.see more
Waterfront Cottage - 10 Mins to Great Barrington!
Clean, attention to detail, everything is updated, fantastic deck, wonderful views.

Loved being so close to Jacob's Pillow and great restaurants (Xochil, Gedney Farm, Dream Away Lodge). Visiting MOCA and the Norman Rockwell were also a wonderful treat. Early dawn and dusk were wonderful at the cottage with daily visits from a bald eagle flying right in front of the deck. Perfect for a restful vacation.see more
Gartner House, a charming home in Lenox
Handy, convenient, comfortable, well equipped and peaceful rental in terrific location.

In some rentals, you have to bring literally everything. This place was just the opposite. Great linens provided, napkins, paper towels and toilet paper and various necessities for cooking. Very roomy with 4 bedrooms and 5 beds, a good shower, hair dryer, washer dryer, good seating in the living room. Good lighting in the bedrooms, so appreciated. Convenient parking, walking distance to the town of Lenox with shops and restaurants at hand. Hope i have the chance to come back.see more
Berkshire Farmhouse Vacation
October in Berkshires

Great location near major attractions such as Tanglewood. Screened porch is great for pre dinner get together. Old house but well maintained except for old house smell. Plenty of room for 6 people. … see more
Fox Hollow Laurel Lake Ranch
Family fun

The layout of this rental really lets you have a space and family time! The large living room and kitchen where a big hit and having the bedrooms on the outside is nice when part of the family wanted to sleep in and others like the early morning coffee. The up keep was also great we did have a small fire alarm issue and management come over and fixed it as well as gave us some vaca tips. It was a great long weekend! Thank you!see more
Berkshires Waterfront Lakehouse Sanctuary
Weekend getaway

Lovely house. Nicely updated. Right next to the bike trail! Beautiful view of the lake. Great family fun. Thank you. … see more

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