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112 Houses
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
Map
Price per night from
$300
Responds fast!
avg. 3 hours 21 minutes
Price per night from
$300
Beautiful Lakefront Berkshire Rental
Berkshires / Monterey
5 6 7 nights min
- 5 bedrooms
- sleeps 6
- 7 nights min
- Beach / lakeside relaxation
- Child Friendly
- Air conditioning
Map
Price per night from
$427
Responds fast!
avg. 3 hours 33 minutes
Price per night from
$427
Spacious Lakeside Berkshire Home
Berkshires / Monterey
4 10 3 nights min
- 4 bedrooms
- sleeps 10
- 3 nights min
- Child Friendly
- Air conditioning
- Private garden
Map
Price per night from
$400
Responds fast!
avg. 3 hours 48 minutes
Price per night from
$400
Fabulous Post & Beam Berkshire Rental
Berkshires / Monterey
7 21 nights min
- sleeps 7
- 21 nights min
- Ask about children
- Car not necessary
- Ask about pets
Map
Price per night from
$179
Price per night from
$179
Great rentals within 20 miles that match your search
Distance approx 16.81 km from Monterey
Great Vacation House in the Berkshires on Richmond Pond
Berkshires / Richmond
2 6 min stay varies
- 2 bedrooms
- sleeps 6
- min stay varies
- Beach / lakeside relaxation
- Child Friendly
- Air conditioning
Price per night from
$186
Price per night from
$186
Distance approx 11.77 km from Monterey
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
Price per night from
$250
Responds fast!
avg. 2 hours 34 minutes
Price per night from
$250
Distance approx 8.6 km from Monterey
Restored 1886 Eyebrow Colonial
Berkshires / Stockbridge
2 6 7 nights min
- 2 bedrooms
- sleeps 6
- 7 nights min
- Child Friendly
- Air conditioning
- Private garden
Price per night from
$214
Price per night from
$214
Distance approx 9.66 km from Monterey
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
$275
Price per night from
$275
Distance approx 3.48 km from Monterey Show on Map
Rustic Berkshires Cottage w/ Views of Lake Buel!
Berkshires / New Marlborough
1 2 7 nights min
- 1 bedroom
- sleeps 2
- 7 nights min
- Pet Friendly
Map
Price per night from
$110
Responds fast!
avg. 10 minutes
Price per night from
$110
Distance approx 12.84 km from Monterey
Comfortable Farmhouse in the Berkshires
Berkshires / West Stockbridge
5 12 2 nights min
- 5 bedrooms
- sleeps 12
- 2 nights min
- Beach / lakeside relaxation
- Child Friendly
- Air conditioning
Price per night from
$325
Price per night from
$325
Distance approx 14.02 km from Monterey
Renovated Barn
Connecticut / Taconic
3 6 2 nights min
- 3 bedrooms
- sleeps 6
- 2 nights min
- Child Friendly
- Air conditioning
- Pet Friendly
Price per night from
$350
Responds fast!
avg. 32 minutes
Price per night from
$350
Distance approx 19.18 km from Monterey
New Timberframe House Rental in the Berkshire Mountains, Masschusetts
Berkshires / Hinsdale
3 6 2 nights min
- 3 bedrooms
- sleeps 6
- 2 nights min
- Child Friendly
- Ask about pets
- Private garden
Price per night from
$145
Price per night from
$145
Distance approx 14.13 km from Monterey
Beautifully decorated & immaculate log chalet
New York / Hillsdale
3 6 2 nights min
- 3 bedrooms
- sleeps 6
- 2 nights min
- Child Friendly
- Air conditioning
Price per night from
$175
Price per night from
$175
Distance approx 14.02 km from Monterey
Plan your holidays in the Berkshires. Forecasting plenty of snow and mild temps.
Berkshires / West Stockbridge
3 8 2 nights min
- 3 bedrooms
- sleeps 8
- 2 nights min
- Beach / lakeside relaxation
- Child Friendly
- Pet Friendly
Price per night from
$275
Price per night from
$275
Distance approx 9.46 km from Monterey
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
$3,600
Price per night from
$3,600
Distance approx 18.99 km from Monterey
4 Bedroom Furnished House in Lakeville Connecticut
Connecticut / Lakeville
4 8 2 nights min
- 4 bedrooms
- sleeps 8
- 2 nights min
- Child Friendly
- Air conditioning
- Ask about pets
Price per night from
$325
Price per night from
$325
Distance approx 10.19 km from Monterey
Lakefront Berkshires Ski/Summer House, Great Views
Berkshires / Great Barrington
4 10 min stay varies
- 4 bedrooms
- sleeps 10
- min stay varies
- Beach / lakeside relaxation
- Child Friendly
- Pet Friendly
Price per night from
$185
Price per night from
$185
Distance approx 11.74 km from Monterey
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
$189
Responds fast!
avg. 35 minutes
Price per night from
$189
Distance approx 5.79 km from Monterey
BERKSHIRES RETREAT-LARGE 6+ BR HOME W/ AMENITIES
Berkshires / Otis
6 14 7 nights min
- 6 bedrooms
- sleeps 14
- 7 nights min
- Ask about children
- Ask about pets
Price per night from
$600
Price per night from
$600
Distance approx 5.23 km from Monterey
Romantic Berkshire Cottage on Storybook Estate
Berkshires / Tyringham
1 2 2 nights min
- 1 bedroom
- sleeps 2
- 2 nights min
- Ask about children
- Pet Friendly
Price per night from
$225
Responds fast!
avg. 1 hour 29 minutes
Price per night from
$225
Distance approx 13.5 km from Monterey
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
$186
Responds fast!
avg. 1 hour 39 minutes
Price per night from
$186
Distance approx 8.42 km from Monterey
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
Price per night from
$200
Responds fast!
avg. 1 hour 45 minutes
Price per night from
$200
Distance approx 10.26 km from Monterey
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
Price per night from
$750
Price per night from
$750
Distance approx 11.19 km from Monterey
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
Price per night from
$700
Price per night from
$700
Distance approx 11.33 km from Monterey
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
Price per night from
$299
Responds fast!
avg. 13 minutes
Price per night from
$299
Distance approx 10.65 km from Monterey
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
Price per night from
$225
Responds fast!
avg. 10 minutes
Price per night from
$225
Distance approx 9.26 km from Monterey
Berkshire House Share-The Blue Room
Berkshires / Lee
3 2 1 night min
- 3 bedrooms
- sleeps 2
- 1 night min
Price per night from
$75
Price per night from
$75
Distance approx 9.09 km from Monterey
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
Price per night from
$210
Responds fast!
avg. 10 minutes
Price per night from
$210
Distance approx 11.4 km from Monterey
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
Price per night from
$285
Responds fast!
avg. 3 hours 47 minutes
Price per night from
$285
Distance approx 9.28 km from Monterey
House share/room for rent
Berkshires / Lee
1 1 1 night min
- 1 bedroom
- sleeps 1
- 1 night min
- Beach / lakeside relaxation
- Nearest beach 3 mi
Price per night from
$67
Price per night from
$67
Distance approx 12.67 km from Monterey
Berkshire Getaway at 'Tofu'S Retreat'
Berkshires / Alford
3 6 7 nights min
- 3 bedrooms
- sleeps 6
- 7 nights min
- Swimming pool
- Child Friendly
- Air conditioning
Price per night from
$215
Responds fast!
avg. 1 hour 10 minutes
Price per night from
$215
Distance approx 15.83 km from Monterey
Colebrook Dream
Connecticut / Colebrook
3 12 2 nights min
- 3 bedrooms
- sleeps 12
- 2 nights min
- Child Friendly
- Air conditioning
- Private garden
Price per night from
$300
Price per night from
$300
Distance approx 8.73 km from Monterey
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
$150
Price per night from
$150
Distance approx 10.66 km from Monterey
Iris Room
Berkshires / Stockbridge
1 2 1 night min
- 1 bedroom
- sleeps 2
- 1 night min
- Child Friendly
- Pet Friendly
- Private garden
Price per night from
$150
Price per night from
$150
Distance approx 9.13 km from Monterey
Private Berkshire Estate w/Pool & Tennis Court
Berkshires / Great Barrington
4 12 min stay varies
- 4 bedrooms
- sleeps 12
- min stay varies
- Swimming pool
- Child Friendly
- Air conditioning
Price per night from
$575
Price per night from
$575
Distance approx 9.81 km from Monterey
Beautifully Renovated Berkshires Farmhouse
Berkshires / West Stockbridge
2 4 2 nights min
- 2 bedrooms
- sleeps 4
- 2 nights min
- Air conditioning
- Private garden
Price per night from
$210
Price per night from
$210
Distance approx 5.16 km from Monterey
Charming and Spacious Colonial Farmhouse on 4 Acre Estate
Berkshires / Tyringham
4 8 2 nights min
- 4 bedrooms
- sleeps 8
- 2 nights min
- Beach / lakeside relaxation
- Nearest beach 2 mi
- Child Friendly
Price per night from
$395
Responds fast!
avg. 1 hour 29 minutes
Price per night from
$395
Distance approx 9.62 km from Monterey
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
$145
Price per night from
$145
What is Certificate of Excellence?
TripAdvisor gives a Certificate of Excellence to accommodations, attractions and restaurants that consistently earn great reviews from travelers.