Beginning of main content

Search over 1,000,000 properties worldwide and 550 airlines worldwide.

Search over a million flights, hotels, packages, and more

No Expedia cancellation fee to change or cancel almost any hotel reservation.


Vacation Rentals in The Berkshires

Estimated price for 1 night/2 adults

Vacation Village in the Berkshires
Vacation Village in the Berkshires
3.0 out of 5.0 276 Brodie Mountain Rd, Hancock, MA
$135
4.2/5 (916 reviews)

It was clean and nice. There were barbecues and a park And a small balcony. The kids had a good time. The walls are thin though. We got woke up in the morning by the people next to us.

Reviewed on Jul 10, 2019
Situated in Hancock, this condo building is within 9 mi (15 km) of Pittsfield State Forest, Mount Greylock State Reservation Visitor Center, and Waubeeka Golf ...
Jiminy Peak Mountain Resort
Jiminy Peak Mountain Resort
3.0 out of 5.0 37 Corey Rd, Hancock, MA
$149
4.0/5 (591 reviews)

The rooms are spacious and nice. The views are great.

Reviewed on Jul 7, 2019
Located in the mountains, this Hancock condo resort offering ski-in/ski-out access is 6.1 mi (9.7 km) from Mount Greylock State Reservation Visitor Center and ...
Holiday Inn Club Vacations Oak n' Spruce Resort
Holiday Inn Club Vacations Oak n' Spruce Resort
3.5 out of 5.0 190 Meadow Street, South Lee, MA
$179
4.3/5 (53 reviews)

This was a beautiful and homey property and the unit was lovely - way bigger than expected!

Reviewed on Jul 8, 2019
This family-friendly South Lee aparthotel is within 3 mi (5 km) of Beartown State Forest, Lee Prime Outlets, and Berkshire Theatre Festival. Mission House and ...
Wyndham Bentley Brook
Wyndham Bentley Brook
3.0 out of 5.0 1 Corey Road, Hancock, MA
4.6/5 (149 reviews)

Fresh clean rooms , very nice staff , kid friendly,

Reviewed on Jun 26, 2019
Situated in the mountains, this eco-friendly condo building is within 9 mi (15 km) of Pittsfield State Forest, Mount Greylock State Reservation Visitor Center, ...
The Ponds at Foxhollow
The Ponds at Foxhollow
3.0 out of 5.0 3 Foxhollow Drive Route 7, Lenox, MA
4.0/5 (27 reviews)

This is a cluster of townhouse style apartment units. The unit we occupied was clean and very well equipped. It is a functional space and comfortable. Great location right outside of Lenox near Lee and Stockbridge. The exterior is not too pleasing- it is a beautiful property that once belonged to ...

Reviewed on Jan 6, 2019
Situated in Lenox, this condo building is within 3 mi (5 km) of The Mount, Animagic Museum of Animation, and Lee Library. Greenock Country Club and Shakespeare ...
Charming, Private Guest Suite-historic New Village in the Berkshires
Charming, Private Guest Suite-historic New Village in the Berkshires
Mill River, Massachusetts
Situated in New Marlborough, this historic vacation home is close to Questing, Umpachene Falls Park, and Dry Hill. Area attractions also include Ski Butternut ...
Heart of the Berkshires
Heart of the Berkshires
3.0 out of 5.0 38 Holmes Road, Pittsfield, MA
$150
Situated in Pittsfield, this vacation home is 1.3 mi (2 km) from Colonial Theater and within 6 mi (10 km) of Pittsfield State Forest and Hancock Shaker Village. ...
Berkshire Lake House Vacation Rental
Berkshire Lake House Vacation Rental
Pittsfield, Massachusetts
Situated in Pittsfield, this vacation home is in the same area as Berkshire Athenaeum, Berkshire Museum, and Colonial Theater. Area attractions also include ...
Tentrr - Running Spring Farm
Tentrr - Running Spring Farm
2.5 out of 5.0 25 Jerusalem Road, Lee, MA
Situated in Lee, this apartment building is within 3 mi (5 km) of Beartown State Forest, Tyringham Cobble, and Goose Pond Reservation. Ashintully Gardens is ...
Map

Vacation Rentals in The Berkshires

Search for Vacation Rentals in The Berkshires on Expedia.com! You can easily find your home rentals, villas, short-term apartments for rent in The Berkshires using one of the methods below: 

  • View our selection of featured home rentals in The Berkshires
  • Use the map to find apartments and other vacation rentals in the The Berkshires neighbourhood you prefer
  • Enter your travel dates to view the best deals on vacation rentals in The Berkshires while they last

Look no further and take a look at our great range of rental properties in The Berkshires!

Other types of properties in The Berkshires you may be interested in

Estimated price for 1 night/2 adults

The Red Lion Inn

The Red Lion Inn

30 Main Street, Stockbridge, MA
  • Free Cancellation
  • Reserve now, pay when you stay
3.5 out of 5.0
 
 

The Red Lion Inn$145

Jul 17 - Jul 18

The Red Lion Inn$145
Yankee Inn

Yankee Inn

461 Pittsfield Rd, Lenox, MA
  • Free Cancellation
  • Reserve now, pay when you stay
2.5 out of 5.0
 
 

Yankee Inn$129

Jul 18 - Jul 19

Yankee Inn$129