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113 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
$344
Responds fast!
avg. 7 minutes
Price per night from
$344
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
$489
Price per night from
$489
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
$458
Price per night from
$458
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
$205
Price per night from
$205
NEW! Monterey Home w/Porch by Beach & State Parks!
Berkshires / Monterey
3 7 min stay varies
- 3 bedrooms
- sleeps 7
- min stay varies
- Ski
- Child Friendly
- Pet Friendly
Map
Price per night from
$229
Responds fast!
avg. 7 minutes
Price per night from
$229
NEW-Pet-Friendly Berkshires Home w/Dock & Fire Pit
Berkshires / Monterey
3 10 7 nights min
- 3 bedrooms
- sleeps 10
- 7 nights min
- Child Friendly
- Pet Friendly
Map
Price per night from
$212
Responds fast!
avg. 7 minutes
Price per night from
$212
Great rentals within 20 miles that match your search
Distance approx 8.42 km from Monterey
chestnut lodge Queens Room
Berkshires / Lee
1 2 2 nights min
- 1 bedroom
- sleeps 2
- 2 nights min
- Ask about pets
Price per night from
$165
Responds fast!
avg. 36 minutes
Price per night from
$165
Distance approx 16.22 km from Monterey
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
$1,369
Price per night from
$1,369
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
$228
Responds fast!
avg. 36 minutes
Price per night from
$228
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
$371
Price per night from
$371
Distance approx 7.91 km from Monterey
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
$343
Price per night from
$343
Distance approx 11.74 km from Monterey
RIVERSONG "PENTHOUSE"
Berkshires / North Egremont
1 2 1 night min
- 1 bedroom
- sleeps 2
- 1 night min
- Air conditioning
- Private garden
Price per night from
$172
Responds fast!
avg. 23 minutes
Price per night from
$172
Distance approx 7.87 km from Monterey
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
$143
Price per night from
$143
Distance approx 14.02 km from Monterey
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
Price per night from
$376
Price per night from
$376
Distance approx 11.96 km from Monterey
Cozy & Modern Home -mins from Tanglewood & Kripalu
Berkshires / West Stockbridge
2 6 1 night min
- 2 bedrooms
- sleeps 6
- 1 night min
- Ask about children
- Air conditioning
- Ask about pets
Price per night from
$115
Responds fast!
avg. 1 hour 29 minutes
Price per night from
$115
Distance approx 9.13 km from Monterey
Garfield House
Maine / Lee
2 6 2 nights min
- 2 bedrooms
- sleeps 6
- 2 nights min
- Child Friendly
- Pet Friendly
Price per night from
$200
Price per night from
$200
Distance approx 10.14 km from Monterey
Beautiful Berkshire Mtn. Condo with Mountain Views, near Tanglewood, Lakes et al
Berkshires / Lee
3 8 30 nights min
- 3 bedrooms
- sleeps 8
- 30 nights min
- Child Friendly
Price per night from
$248
Price per night from
$248
Distance approx 10.58 km from Monterey
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. 10 minutes
Price per night from
$858
Distance approx 4.77 km from Monterey
Country Victorian Serenity in the Berkshires
Berkshires / New Marlborough
4 6 7 nights min
- 4 bedrooms
- sleeps 6
- 7 nights min
- Suitable for children age 5+
- Private garden
Price per night from
$262
Price per night from
$262
Distance approx 17.31 km from Monterey
Cottage on East Twin Lakes, Internet Access, A/C.
Connecticut / Salisbury
3 6 7 nights min
- 3 bedrooms
- sleeps 6
- 7 nights min
- Child Friendly
- Air conditioning
Price per night from
$180
Price per night from
$180
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
$172
Responds fast!
avg. 3 hours 37 minutes
Price per night from
$172
Distance approx 16.67 km from Monterey
Mountain Views Atop Blueberry Hill on 40 Acres
New York / Austerlitz
3 6 2 nights min
- 3 bedrooms
- sleeps 6
- 2 nights min
- Child Friendly
- Pet Friendly
Price per night from
$229
Price per night from
$229
Distance approx 7.68 km from Monterey
Designer Loft Style Residence
Berkshires / Sheffield
3 6 7 nights min
- 3 bedrooms
- sleeps 6
- 7 nights min
- Child Friendly
- Air conditioning
- Pet Friendly
Price per night from
$515
Price per night from
$515
Distance approx 16.07 km from Monterey
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
$200
Price per night from
$200
Distance approx 9.1 km from Monterey
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
$223
Price per night from
$223
Distance approx 8.76 km from Monterey
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
Price per night from
$343
Price per night from
$343
Distance approx 9.18 km from Monterey
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
Price per night from
$178
Responds fast!
avg. 36 minutes
Price per night from
$178
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
$258
Responds fast!
avg. 10 minutes
Price per night from
$258
Distance approx 18.08 km from Monterey
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 26 minutes
Price per night from
$229
Distance approx 13.79 km from Monterey
Charming 2+2 Lakeside Cottage on Best Lake in CT
Connecticut / Salisbury
2 4 30 nights min
- 2 bedrooms
- sleeps 4
- 30 nights min
- Beach / lakeside relaxation
- Child Friendly
Price per night from
$206
Price per night from
$206
Distance approx 9.15 km from Monterey
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 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
$258
Responds fast!
avg. 1 hour 43 minutes
Price per night from
$258
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
$166
Price per night from
$166
Distance approx 5.23 km from Monterey
Berkshire Getaway ~ Romantic Tower Suite on Storybook Estate
Berkshires / Tyringham
1 4 2 nights min
- 1 bedroom
- sleeps 4
- 2 nights min
- Ask about children
- Ask about pets
Price per night from
$287
Responds fast!
avg. 1 hour 43 minutes
Price per night from
$287
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
$343
Responds fast!
avg. 12 minutes
Price per night from
$343
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
$216
Price per night from
$216
Distance approx 13.88 km from Monterey
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 18.3 km from Monterey
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
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