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136 Houses
NEW! Cozy Lenox Home 1.5 Mi. to Tanglewood Music!
Berkshires / Lenox
3 6 3 nights min
- 3 bedrooms
- sleeps 6
- 3 nights min
- Child Friendly
- Air conditioning
Map
Price per night from
$264
Responds fast!
avg. 58 minutes
Price per night from
$264
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
INTERIOR DESIGNERS BOTANICAL GARDENS
Berkshires / Lenox
1 5 2 nights min
- 1 bedroom
- sleeps 5
- 2 nights min
- Nearest beach 3 mi
- Child Friendly
- Air conditioning
Map
Price per night from
$132
Price per night from
$132
Heart of the Berkshires!
Berkshires / Lenox
3 6 2 nights min
- 3 bedrooms
- sleeps 6
- 2 nights min
- Child Friendly
- Air conditioning
- Pet Friendly
Map
Price per night from
$258
Price per night from
$258
Heart of Lenox
Berkshires / Lenox
2 4 2 nights min
- 2 bedrooms
- sleeps 4
- 2 nights min
- Child Friendly
- Air conditioning
- Private garden
Map
Price per night from
$201
Responds fast!
avg. 2 hours 17 minutes
Price per night from
$201
Renovated 2 bedroom in Heart of Lenox
Berkshires / Lenox
2 4 1 night min
- 2 bedrooms
- sleeps 4
- 1 night min
- Child Friendly
- Air conditioning
Map
Price per night from
$344
Price per night from
$344
NEW! House w/ Kayak - Walk to Stockbridge Bowl!
Berkshires / Lenox
3 6 min stay varies
- 3 bedrooms
- sleeps 6
- min stay varies
- Ski
- Child Friendly
- Air conditioning
Map
Price per night from
$212
Responds fast!
avg. 58 minutes
Price per night from
$212
Great rentals within 20 miles that match your search
Distance approx 13.58 km from Lenox
Berkshire Home on Lake Garfield w/Dock & Boats
Berkshires / Monterey
4 12 min stay varies
- 4 bedrooms
- sleeps 12
- min stay varies
- Ski
- Child Friendly
- Air conditioning
Price per night from
$345
Responds fast!
avg. 58 minutes
Price per night from
$345
Distance approx 8.67 km from Lenox
Big Beautiful 7 bedroom 3 bath hot tub pool table
Berkshires / Pittsfield
7 18 2 nights min
- 7 bedrooms
- sleeps 18
- 2 nights min
- Child Friendly
- Ask about pets
Price per night from
$345
Price per night from
$345
Distance approx 3.26 km from Lenox Show on Map
Cozy Modern Condo for the Berkshires
Berkshires / West Stockbridge
2 6 1 night min
- 2 bedrooms
- sleeps 6
- 1 night min
- Child Friendly
- Air conditioning
- Pet Friendly
Map
Price per night from
$288
Responds fast!
avg. 1 hour 23 minutes
Price per night from
$288
Distance approx 13.83 km from Lenox
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
$259
Price per night from
$259
Distance approx 12.29 km from Lenox
Spacious wooded home
Berkshires / Becket
4 12 3 nights min
- 4 bedrooms
- sleeps 12
- 3 nights min
- Beach / lakeside relaxation
- Private garden
Price per night from
$225
Price per night from
$225
Distance approx 11.83 km from Lenox
Beauty in the Berkshires
New York / Austerlitz
6 14 2 nights min
- 6 bedrooms
- sleeps 14
- 2 nights min
- Child Friendly
Price per night from
$1,381
Price per night from
$1,381
Distance approx 13.99 km from Lenox
Quiet Comfortable Cabin 5 Min. Walk to Lake
Berkshires / Becket
2 4 2 nights min
- 2 bedrooms
- sleeps 4
- 2 nights min
- Child Friendly
- Air conditioning
- Ask about pets
Price per night from
$171
Price per night from
$171
Distance approx 12.25 km from Lenox
Spacious Lakeside Berkshire Home
Berkshires / Monterey
4 10 3 nights min
- 4 bedrooms
- sleeps 10
- 3 nights min
- Child Friendly
- Air conditioning
- Private garden
Price per night from
$460
Price per night from
$460
Distance approx 4.42 km from Lenox 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
$379
Price per night from
$379
Distance approx 11.69 km from Lenox
Gem of the Berkshires, walk to downtown & lake.
Berkshires / Great Barrington
5 12 2 nights min
- 5 bedrooms
- sleeps 12
- 2 nights min
- Nearest beach 0.32 mi
- Child Friendly
- Air conditioning
Price per night from
$345
Price per night from
$345
Distance approx 11.54 km from Lenox
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
$461
Price per night from
$461
Distance approx 11.85 km from Lenox
Berkshires on the Pond
Berkshires / Becket
2 2 4 nights min
- 2 bedrooms
- sleeps 2
- 4 nights min
- Nearest beach 16 mi
- Ask about children
- Private garden
Price per night from
$144
Price per night from
$144
Distance approx 15.61 km from Lenox
Berkshires Cottage Country Retreat
New York / Stephentown
3 6 2 nights min
- 3 bedrooms
- sleeps 6
- 2 nights min
- Private garden
Price per night from
$190
Responds fast!
avg. 2 hours 19 minutes
Price per night from
$190
Distance approx 16.41 km from Lenox
Berkshire Country Estate - The Library Suite
New York / Old Chatham
2 4 2 nights min
- 2 bedrooms
- sleeps 4
- 2 nights min
- Child Friendly
Price per night from
$173
Price per night from
$173
Distance approx 15.44 km from Lenox
Spacious Berkshires Home w/ Pool & Patio!
Berkshires / North Egremont
5 10 2 nights min
- 5 bedrooms
- sleeps 10
- 2 nights min
- Swimming pool
- Ski
- Child Friendly
Price per night from
$858
Responds fast!
avg. 9 minutes
Price per night from
$858
Distance approx 5.73 km from Lenox Show on Map
the BIG room at chestnut lodge
Berkshires / Lee
1 6 2 nights min
- 1 bedroom
- sleeps 6
- 2 nights min
- Ask about children
- Pet Friendly
Map
Price per night from
$230
Responds fast!
avg. 36 minutes
Price per night from
$230
Distance approx 5.73 km from Lenox Show on Map
Writer's Room at Chestnut Lodge
Berkshires / Lee
1 2 2 nights min
- 1 bedroom
- sleeps 2
- 2 nights min
- Nearest beach 8 mi
- Ask about children
- Air conditioning
Map
Price per night from
$205
Responds fast!
avg. 36 minutes
Price per night from
$205
Distance approx 3.54 km from Lenox Show on Map
New Pristine Berkshire Vacation Rental with Pool (5 miles Tanglewood)
Berkshires / Richmond
3 6 7 nights min
- 3 bedrooms
- sleeps 6
- 7 nights min
- Swimming pool
- Child Friendly
- Air conditioning
Map
Price per night from
$572
Price per night from
$572
Distance approx 5.73 km from Lenox Show on Map
chestnut lodge Queens Room
Berkshires / Lee
1 2 2 nights min
- 1 bedroom
- sleeps 2
- 2 nights min
- Ask about pets
Map
Price per night from
$167
Responds fast!
avg. 36 minutes
Price per night from
$167
Distance approx 7.14 km from Lenox
Cedar Chest
New York / Canaan
1 2 7 nights min
- 1 bedroom
- sleeps 2
- 7 nights min
- Beach / lakeside relaxation
- Nearest beach 2 mi
- Air conditioning
Price per night from
$115
Price per night from
$115
Distance approx 16.41 km from Lenox
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
$196
Price per night from
$196
Distance approx 6.63 km from Lenox
Deluxe New Home, 2 Master Suites, Tanglewood Area
Berkshires / Lee
5 12 3 nights min
- 5 bedrooms
- sleeps 12
- 3 nights min
- Child Friendly
Price per night from
$863
Price per night from
$863
Distance approx 3.76 km from Lenox 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
$87
Price per night from
$87
Distance approx 13.64 km from Lenox
Larger Than Life 1 BR Sleeps 8 Bentley Brook Resort
Berkshires / Hancock
1 8 3 nights min
- 1 bedroom
- sleeps 8
- 3 nights min
- Child Friendly
Price per night from
$517
Price per night from
$517
Distance approx 10.69 km from Lenox
Cozy and clean in Gt Barrington- available for October
Berkshires / Great Barrington
2 4 3 nights min
- 2 bedrooms
- sleeps 4
- 3 nights min
- Nearest beach 2 mi
- Child Friendly
- Pet Friendly
Price per night from
$173
Responds fast!
avg. 3 hours 37 minutes
Price per night from
$173
Distance approx 18.14 km from Lenox
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
$576
Price per night from
$576
Distance approx 17.05 km from Lenox
Golden Triangle in the Berkshires
Berkshires / Hancock
2 4 2 nights min
- 2 bedrooms
- sleeps 4
- 2 nights min
- Child Friendly
- Air conditioning
Price per night from
$2,873
Price per night from
$2,873
Distance approx 13.63 km from Lenox
Jiminy Peak Ski Resort-Country Village's Best Unit
Berkshires / Hancock
2 6 1 night min
- 2 bedrooms
- sleeps 6
- 1 night min
- Child Friendly
Price per night from
$288
Responds fast!
avg. 16 minutes
Price per night from
$288
Distance approx 13.23 km from Lenox
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 9.11 km from Lenox
NEW! Lakefront Berkshires House w/Deck, Dock +Boat
Berkshires / Housatonic
4 10 min stay varies
- 4 bedrooms
- sleeps 10
- min stay varies
- Ski
- Child Friendly
- Pet Friendly
Price per night from
$195
Responds fast!
avg. 21 minutes
Price per night from
$195
Distance approx 7.54 km from Lenox
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
Price per night from
$328
Price per night from
$328
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