Stockbridge Holiday Rentals
Plan, book, stay with confidence
Be picky
Search almost a million properties worldwide
Change your mind
Book hotels with free cancellation
Holiday Rentals in Stockbridge
Rockspring by AvantStay | Huge Berkshires Estate
Rockspring by AvantStay | Huge Berkshires Estate
8.8 out of 10, Excellent, (10)
Stockbridge Home, Come Experience The Berkshires!
Stockbridge Home, Come Experience The Berkshires!
10.0 out of 10, Exceptional, (11)
Find your Sanctuary at The Rectory at Stockbridge
Find your Sanctuary at The Rectory at Stockbridge
10.0 out of 10, Exceptional, (2)
The price is HK$4,601
HK$7,762 total
includes taxes & fees
26 May - 27 May
Save an average of 15% on thousands of hotels when you're signed in
Jiminy Peak Mountain Resort
Jiminy Peak Mountain Resort
8.2 out of 10, Very good, (857)
The price is HK$1,162
HK$1,275 total
includes taxes & fees
22 May - 23 May
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
The Freeman - Newly Renovated 14K SF Estate on 40 Acres
10.0 out of 10, Exceptional, (29)
Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
9.8 out of 10, Exceptional, (32)
Peace and quiet on the lake
Peace and quiet on the lake
9.6 out of 10, Exceptional, (184)
Pristine Home In Becket Woods
Pristine Home In Becket Woods
10.0 out of 10, Exceptional, (7)
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
Quiet Comfortable Cabin 5 Min. Walk to Swimming and Boating
9.6 out of 10, Exceptional, (195)
Serene Acreage - Pond - Hiking Trails Nearby
Serene Acreage - Pond - Hiking Trails Nearby
10.0 out of 10, Exceptional, (4)
Private Estate, Heated YEARROUND Outdoor Pool
Private Estate, Heated YEARROUND Outdoor Pool
10.0 out of 10, Exceptional, (8)
Tree-lined Home, Large Yard, Pool, & Dog-Friendly.
Tree-lined Home, Large Yard, Pool, & Dog-Friendly.
6.0 out of 10, (2)
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
7.2 out of 10, Good, (39)
Berkshire Village Carriage House - Super Private!!
Berkshire Village Carriage House - Super Private!!
9.8 out of 10, Exceptional, (203)
Fox Hollow Luxury Ranch Laurel Lake
Fox Hollow Luxury Ranch Laurel Lake
9.4 out of 10, Exceptional, (12)
Berkshires Cabin 2 Mi to Appalachian Trail!
Berkshires Cabin 2 Mi to Appalachian Trail!
9.8 out of 10, Exceptional, (6)
The Meadows House @ Otis Ridge w/ 7-person hot tub
The Meadows House @ Otis Ridge w/ 7-person hot tub
9.8 out of 10, Exceptional, (20)
Berkshire Lake access
Berkshire Lake access
10.0 out of 10, Exceptional, (41)
Private Island - Largest Fresh Water Reservoir in Mass....
Private Island - Largest Fresh Water Reservoir in Mass....
10.0 out of 10, Exceptional, (3)
Beautiful Estate: Pool, Pond, Arcade, Gym, Library, Barn, Trails Reduced Rates!
Beautiful Estate: Pool, Pond, Arcade, Gym, Library, Barn, Trails Reduced Rates!
9.6 out of 10, Exceptional, (79)
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Other types of properties in Stockbridge you may be interested in
The Red Lion Inn
The Red Lion Inn
8.8 out of 10, Excellent, (885)
The price is HK$1,118
HK$1,424 total
includes taxes & fees
22 May - 23 May
Rockspring by AvantStay | Huge Berkshires Estate
Rockspring by AvantStay | Huge Berkshires Estate
8.8 out of 10, Excellent, (10)
Stockbridge Home, Come Experience The Berkshires!
Stockbridge Home, Come Experience The Berkshires!
10.0 out of 10, Exceptional, (11)
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Search for holiday rentals in Stockbridge on Expedia! You can easily find your home rentals, villas, holiday apartments in Stockbridge using one of the methods below:
- View our selection of featured holiday rentals in Stockbridge
- Use the map to find apartments and other holiday homes in the Stockbridge neighbourhood you prefer
- Enter your travel dates to view the best deals on holiday rentals in Stockbridge while they last
Look no further and take a look at our great range of rental properties in Stockbridge!
Frequently asked questions
Recent reviews of Stockbridge propertiesExpedia verified reviews
5/5 Excellent
"Stayed a couple years ago got same room this time can’t complain."
A verified traveller stayed at Hampton Inn & Suites Berkshires-Lenox
Posted 1 day ago