Vacation Rentals & Apartments in Berkshires

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57 apartments

Enjoy horses and the largest recreational lake in Massachusetts

East Otis apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$127

Escape to the Berkshires!

Becket house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Responds fast! avg. 3 hours 11 minutes

Price per night from

$316

New Timberframe House Rental in the Berkshire Mountains, Masschusetts

Hinsdale house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$218

Christmas in The Berkshires

Hancock condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

Price per night from

$259

Lakefront Berkshires Ski/Summer House, Great Views

Great Barrington house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

Price per night from

$251

Spacious Lakeside Berkshire Home

Monterey house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

Price per night from

$574

Quiet Comfortable Cabin 5 Min. Walk to Lake

Becket house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

“awesome beautiful place” I can't say enough about this. Place, perfect I guess Serene, peaceful,beautiful, quiet. Djuna the owner is Sweet and very efficient and provides every detail. The Whole are is perfect Oct a getaway, things to do places To shop,eat or just cuddle in with a fire. We will Definetly be returning as soon as we can.:)))

Price per night from

$171

Berkshires: Romantic Cottage with spectacular view

Great Barrington cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

“A Real Gem!!!” This cottage is the perfect place for two people. It is truly as beautiful as the pictures! The pool and grounds are exceptional and the view is breathtaking. The place is extremely well maintained and the owner is very kind and helpful. We had a fabulous weekend here and would gladly return!

Price per night from

$275

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

$230

Whitman Woods - A Berkshire Vacation

Hancock house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$173

Retreat in the Woods

Savoy house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$230

Fabulous Post & Beam Berkshire Rental

Monterey house

  • 2 bathrooms
  • sleeps 7

Price per night from

$206

Lake House

Lee house

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 9

Price per night from

$820

Berkshires Spacious Comfortable Charming Farmhouse

Lee apartment

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

“lovely stay” The house is comfortable, clean, and convenient to Lenox, Stockbridge, and the rest of the Berkshires. Traffic from the street can be a bit loud at times, but it quiets down at night.

Price per night from

$373

Berkshire Farmhouse Vacation

West Stockbridge house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 15

“Quaint Getaway” We were 2 families with 5 kids staying for the weekend. We had plenty of space to spread out, cook & dine together and lots of bedroom options to meet everyone's needs. The house had a lot of antique charm like exposed beams in the living room and paneled walls in the dining room. We were there on a rainy, cold weekend, so did not have an opportunity to enjoy the grounds or porch, but imagine it would be lovely in the warmer weather. Elaine (and her shop) were on the same grounds and she was available for questions about the area. Overall a very relaxing & convenient experience.

Price per night from

$299

Vacation Home on 10 Acres with Pool and Spa

Stockbridge house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$861

Heart of Lenox

Lenox house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Responds fast! avg. 1 hour 12 minutes

Price per night from

$345

Horse Room

Stockbridge farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

Price per night from

$173

One of the Finest Homes and Best location in the Berkshires

Stockbridge house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Price per night from

$804

Thanksgiving week lux condo/4 Berkshires

Williamstown condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$263

Eco-friendly cozy home in Gt. Barrington

Great Barrington house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$173

Deluxe New Home, 2 Master Suites, Tanglewood Area

Lee house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 12

Price per night from

$861

Iris Room

Stockbridge farmhouse

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$173

Golden Triangle in the Berkshires

Hancock house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$2,869

Responds fast! avg. 1 hour 31 minutes

Price per night from

$122

Restored 1881 Farm House

Lenox house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$572

Private Home Overlooking Stevens Lake (31 Night Min)

Great Barrington house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$572

The Bear Den

North Adams apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Price per night from

$339

The Gatehouse on Golden Hill

Lee house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 10

Price per night from

$744

Expansive Berkshire Property

Stockbridge house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Price per night from

$458

Newly Renovated Colonial on the River! Sleeps 5-6

Stockbridge house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

Price per night from

$327

** Private Berkshire Escape** Monthly Pricing Available

Lee house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

Price per night from

$659

Beautiful Berkshires Historic Lenox Home

Lenox house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$172

Spacious Contemporary With Beautiful Gardens

Housatonic house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Price per night from

$683

The Heart of Berkshires

Lee house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

Price per night from

$402

1880s Home with a Postcard View

Williamstown house

  • 4 bedrooms
  • 1 bathroom
  • sleeps 8

Price per night from

$195

Private Berkshire County Retreat

Sheffield house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Price per night from

$686

Holiday Inn Club Vacations Oak N' Spruce 2br suite Friday check-ins

South Lee condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$70

Viewing 38 of 57
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

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
Quiet Comfortable Cabin 5 Min. Walk to Lake
Nice and cozy

The cabin was just as we expected. It was clean, comfortable, and had all the necessities we needed. The weather was a bit chilly, so we were not able to check out the lake. We would definitely stay in this cabin again. … see more
Eco-friendly cozy home in Gt. Barrington
Easy, comfortable summer getaway!

My cousin and I thoroughly enjoyed our stay. The house was cozy and very convenient for our needs. Having a laundry room just off the kitchen was great when we came back from the lake, the bedrooms were airy with cross ventilation and the screened in porch was a great place to linger over coffee in the morning. The location is also wonderful! It is only a 5 minute drive to lake Mansfield, 7or 8 minutes to downtown GB and a half our or less to Tanglewood. All in all we were very pleased with this quaint, little house.see more
Berkshires: Romantic Cottage with spectacular view
the cottage description is a perfect fit "romantic getaway in id

We have stayed in many B&B;'s and cottage rentals on the east coast...this experience was one of the best! The owners are exceptional hosts and the accommodations are just as described...even better. The setting in the berkshires is fabulous and the location is a perfect location for touring the area (western ma and the Hudson valley). The hosts provide ample information about great restaurants and lovely walks/hikes in the area. We are already planning our next trip to the cottage!see more

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