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141 Houses
Restored 1886 Eyebrow Colonial
Berkshires / Stockbridge
2 6 7 nights min
- 2 bedrooms
- sleeps 6
- 7 nights min
- Child Friendly
- Air conditioning
- Private garden
Map
Price per night from
$245
Price per night from
$245
Beautiful Vacation Home
Berkshires / Stockbridge
4 12 min stay varies
- 4 bedrooms
- sleeps 12
- min stay varies
- Beach / lakeside relaxation
- Child Friendly
- Car not necessary
Map
Price per night from
$572
Price per night from
$572
Stockbridge Bowl - Beach Lake Cottage near Tanglewood (1.8 miles) & Kripalu
Berkshires / Stockbridge
2 4 min stay varies
- 2 bedrooms
- sleeps 4
- min stay varies
- Air conditioning
Map
Price per night from
$343
Responds fast!
avg. 12 minutes
Price per night from
$343
3BD Newly Rennovated Contempoary Near Stockbridge
Berkshires / Stockbridge
3 6 3 nights min
- 3 bedrooms
- sleeps 6
- 3 nights min
- Child Friendly
- Air conditioning
- Private garden
Map
Price per night from
$344
Price per night from
$344
Fabulous NEW Spacious House in the Berkshires Tanglewood
Berkshires / Stockbridge
4 8 min stay varies
- 4 bedrooms
- sleeps 8
- min stay varies
- Child Friendly
- Air conditioning
- Pet Friendly
Map
Price per night from
$287
Responds fast!
avg. 2 hours 1 minutes
Price per night from
$287
Vacation Home on 10 Acres with Pool and Spa
Berkshires / Stockbridge
3 6 7 nights min
- 3 bedrooms
- sleeps 6
- 7 nights min
- Child Friendly
- Ask about pets
Map
Price per night from
$859
Price per night from
$859
Tranquil 3BR Stockbridge House w/Private Deck
Berkshires / Stockbridge
3 6 min stay varies
- 3 bedrooms
- sleeps 6
- min stay varies
- Ski
- Child Friendly
- Air conditioning
Map
Price per night from
$258
Responds fast!
avg. 13 minutes
Price per night from
$258
One of the Finest Homes and Best location in the Berkshires
Berkshires / Stockbridge
4 10 2 nights min
- 4 bedrooms
- sleeps 10
- 2 nights min
- Child Friendly
- Air conditioning
- Pet Friendly
Map
Price per night from
$802
Price per night from
$802
Family-friendly Cottage Near Lake, Tanglewood
Berkshires / Stockbridge
3 7 2 nights min
- 3 bedrooms
- sleeps 7
- 2 nights min
- Beach / lakeside relaxation
- Nearest beach 0.2 mi
- Child Friendly
Map
Price per night from
$327
Responds fast!
avg. 3 hours 27 minutes
Price per night from
$327
Horse Room
Berkshires / Stockbridge
1 3 1 night min
- 1 bedroom
- sleeps 3
- 1 night min
- Child Friendly
- Pet Friendly
- Private garden
Map
Price per night from
$172
Price per night from
$172
Cozy Stockbridge Home - Walk To Golf Course!
Berkshires / Stockbridge
2 6 min stay varies
- 2 bedrooms
- sleeps 6
- min stay varies
- Ski
- Child Friendly
- Air conditioning
Map
Price per night from
$241
Responds fast!
avg. 13 minutes
Price per night from
$241
Iris Room
Berkshires / Stockbridge
1 2 1 night min
- 1 bedroom
- sleeps 2
- 1 night min
- Child Friendly
- Pet Friendly
- Private garden
Map
Price per night from
$172
Price per night from
$172
Nasturtium Room
Berkshires / Stockbridge
1 3 1 night min
- 1 bedroom
- sleeps 3
- 1 night min
- Child Friendly
- Pet Friendly
- Private garden
Map
Price per night from
$172
Price per night from
$172
|The Escape |STOCKBRIDGE| NEW Home |BERKSHIRES|
Berkshires / Stockbridge
4 9 min stay varies
- 4 bedrooms
- sleeps 9
- min stay varies
- Child Friendly
- Air conditioning
- Pet Friendly
Map
Price per night from
$516
Responds fast!
avg. 1 hour 21 minutes
Price per night from
$516
Newly Renovated Colonial on the River! Sleeps 5-6
Berkshires / Stockbridge
3 5 3 nights min
- 3 bedrooms
- sleeps 5
- 3 nights min
- Beach / lakeside relaxation
- Child Friendly
Map
Price per night from
$327
Price per night from
$327
Great rentals within 20 miles that match your search
Distance approx 19.18 km from Stockbridge
2200sf Country House on 16 Acres-2 Miles to Jiminy
Berkshires / Hancock
4 9 2 nights min
- 4 bedrooms
- sleeps 9
- 2 nights min
- Child Friendly
- Pet Friendly
Price per night from
$258
Price per night from
$258
Distance approx 8.13 km from Stockbridge
Hillhouse Log Cabin
New York / Hillsdale
3 13 2 nights min
- 3 bedrooms
- sleeps 13
- 2 nights min
- Beach / lakeside relaxation
- Child Friendly
- Air conditioning
Price per night from
$487
Price per night from
$487
Distance approx 12.47 km from Stockbridge
Escape to the Berkshires!
Berkshires / Becket
4 8 2 nights min
- 4 bedrooms
- sleeps 8
- 2 nights min
- Child Friendly
- Pet Friendly
Price per night from
$315
Price per night from
$315
Distance approx 17.06 km from Stockbridge
The Meadow House 4 bdrm 4 bath house
New York / Stephentown
4 12 2 nights min
- 4 bedrooms
- sleeps 12
- 2 nights min
- Ask about children
- Air conditioning
- Pet Friendly
Price per night from
$722
Price per night from
$722
Distance approx 5.49 km from Stockbridge Show on Map
Gartner House, a charming home in Lenox
Berkshires / Lenox
4 7 2 nights min
- 4 bedrooms
- sleeps 7
- 2 nights min
- Child Friendly
- Car not necessary
- Ask about pets
Map
Price per night from
$229
Price per night from
$229
Distance approx 16.72 km from Stockbridge
Newly Renovated Lakefront Getaway on Robinson Pond
New York / Copake
3 5 3 nights min
- 3 bedrooms
- sleeps 5
- 3 nights min
- Beach / lakeside relaxation
- Nearest beach 0 mi
- Child Friendly
Price per night from
$229
Responds fast!
avg. 2 hours 41 minutes
Price per night from
$229
Distance approx 16.48 km from Stockbridge
Historic Home on 8.5 Acres
Berkshires / Dalton
3 9 3 nights min
- 3 bedrooms
- sleeps 9
- 3 nights min
- Swimming pool
- Child Friendly
- Air conditioning
Price per night from
$458
Price per night from
$458
Distance approx 19.72 km from Stockbridge
Escape to Avalon Cottage in the Hudson Valley
New York / Craryville
3 5 3 nights min
- 3 bedrooms
- sleeps 5
- 3 nights min
- Child Friendly
Price per night from
$166
Price per night from
$166
Distance approx 6.75 km from Stockbridge
Berkshires: Romantic Cottage with spectacular view
Berkshires / Great Barrington
1 3 min stay varies
- 1 bedroom
- sleeps 3
- min stay varies
- Nearest beach 2 mi
- Swimming pool
- Ask about children
Price per night from
$228
Price per night from
$228
Distance approx 5.44 km from Stockbridge Show on Map
To Ski or Not to Ski? Great conditions Great fireplace.Your Choice.
Berkshires / West Stockbridge
3 8 min stay varies
- 3 bedrooms
- sleeps 8
- min stay varies
- Beach / lakeside relaxation
- Child Friendly
- Pet Friendly
Map
Price per night from
$377
Price per night from
$377
Distance approx 8.37 km from Stockbridge
Certificate of Excellence
RiverSong Suite In The Berkshires
Berkshires / North Egremont
1 2 1 night min
- 1 bedroom
- sleeps 2
- 1 night min
- Beach / lakeside relaxation
- Nearest beach 2 mi
- Air conditioning
Certificate of Excellence
Price per night from
$217
Responds fast!
avg. 33 minutes
Price per night from
$217
Distance approx 4.83 km from Stockbridge
Stunning Home! 120 Acres! Amazing!
Berkshires / Great Barrington
9 16 3 nights min
- 9 bedrooms
- sleeps 16
- 3 nights min
- Swimming pool
- Child Friendly
- Air conditioning
Price per night from
$4,122
Price per night from
$4,122
Distance approx 12.03 km from Stockbridge
S. Berkshires Mountain Treehouse • Views • Privacy
Berkshires / Great Barrington
2 4 14 nights min
- 2 bedrooms
- sleeps 4
- 14 nights min
- Child Friendly
- Pet Friendly
Price per night from
$213
Responds fast!
avg. 1 hour 16 minutes
Price per night from
$213
Distance approx 5.76 km from Stockbridge
ground floor garden room
Berkshires / Lee
1 2 2 nights min
- 1 bedroom
- sleeps 2
- 2 nights min
- Nearest beach 5 mi
- Ask about children
- Ask about pets
Price per night from
$91
Responds fast!
avg. 36 minutes
Price per night from
$91
Distance approx 13.15 km from Stockbridge
Overnight at Althouse -Higgins
New York / Hillsdale
2 4 2 nights min
- 2 bedrooms
- sleeps 4
- 2 nights min
- Child Friendly
- Air conditioning
Price per night from
$201
Price per night from
$201
Distance approx 17.52 km from Stockbridge
Berkshire Blueberry Lodge LLC - Near Jiminy Peak
New York / Stephentown
4 10 2 nights min
- 4 bedrooms
- sleeps 10
- 2 nights min
- Child Friendly
- Private garden
Price per night from
$430
Responds fast!
avg. 1 hour 50 minutes
Price per night from
$430
Distance approx 3.59 km from Stockbridge Show on Map
Garfield House
Maine / Lee
2 6 2 nights min
- 2 bedrooms
- sleeps 6
- 2 nights min
- Child Friendly
- Pet Friendly
Map
Price per night from
$201
Price per night from
$201
Distance approx 3.76 km from Stockbridge Show on Map
Berkshire House Share-The Blue Room
Berkshires / Lee
3 2 1 night min
- 3 bedrooms
- sleeps 2
- 1 night min
Map
Price per night from
$86
Price per night from
$86
Distance approx 2.83 km from Stockbridge Show on Map
Rustic Rivers end room in the barn at chestnut lodge
Berkshires / Lee
1 4 2 nights min
- 1 bedroom
- sleeps 4
- 2 nights min
- Ask about pets
- Private garden
Map
Price per night from
$178
Responds fast!
avg. 36 minutes
Price per night from
$178
Distance approx 17.35 km from Stockbridge
Berkshire Country Estate - Rose Suite
New York / Old Chatham
2 4 2 nights min
- 2 bedrooms
- sleeps 4
- 2 nights min
- Child Friendly
Price per night from
$195
Price per night from
$195
Distance approx 12.62 km from Stockbridge
The perfect Southern Berkshire winter vacation esc
Berkshires / Sheffield
4 10 7 nights min
- 4 bedrooms
- sleeps 10
- 7 nights min
- Swimming pool
- Child Friendly
- Air conditioning
Price per night from
$573
Price per night from
$573
Distance approx 12.01 km from Stockbridge
Modern Cozy Wooded Retreat
New York / Spencertown
2 6 30 nights min
- 2 bedrooms
- sleeps 6
- 30 nights min
- Beach / lakeside relaxation
- Child Friendly
- Air conditioning
Price per night from
$153
Price per night from
$153
Distance approx 12.98 km from Stockbridge
Serene Lakefront Cottage
Berkshires / Becket
2 6 min stay varies
- 2 bedrooms
- sleeps 6
- min stay varies
- Child Friendly
- Air conditioning
- Pet Friendly
Price per night from
$171
Price per night from
$171
What is Certificate of Excellence?
TripAdvisor gives a Certificate of Excellence to accommodations, attractions and restaurants that consistently earn great reviews from travelers.