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Search results; Over 1,000 homes in Monterey

Top guest favourite
Home in Monterey
Jaw dropping mountain & lake views
4 bedrooms, 4 beds, 2 bathrooms
16–21 Aug
,
4.96 out of 5 average rating, 303 reviews
Superhost
Cabin in Monterey
Secluded cabin with babbling brook
3 bedrooms, 3 beds, 1 bathroom
28 Aug – 2 Sept
4.87 out of 5 average rating, 253 reviews
Guest favourite
Home in Monterey
Charming cottage w/ gorgeous views.
2 bedrooms, 2 beds, 2 bathrooms
29 Aug – 3 Sept
4.93 out of 5 average rating, 366 reviews
Superhost
Home in Monterey
Dog-Friendly Berkshires Retreat w/Fenced Yard
3 bedrooms, 3 beds, 2.5 bathrooms
11–16 Jul
New place to stay
Top guest favourite
Cottage in Monterey
Beaver Lodge
3 bedrooms, 3 queen beds, 1.5 bathrooms
10–15 Sept
5.0 out of 5 average rating, 82 reviews
Guest favourite
Home in Great Barrington
Lovely house in the Berkshires
3 bedrooms, 4 beds, 1.5 bathrooms
7–12 Sept
4.96 out of 5 average rating, 23 reviews
Guest favourite
Home in Monterey
Forest Hollow | Waterfront • Kayaks • Wood Stove
3 bedrooms, 4 beds, 1.5 bathrooms
30 Aug – 4 Sept
4.84 out of 5 average rating, 96 reviews
Home in Monterey
Contemporary Modern Mountain Retreat
4 bedrooms, 8 beds, 3 bathrooms
28 Sept – 3 Oct
5.0 out of 5 average rating, 4 reviews
Top guest favourite
Chalet in Monterey
Cozy French Country Chalet
2 bedrooms, 3 beds, 1 bathroom
11–16 Sept
4.98 out of 5 average rating, 94 reviews
Top guest favourite
Home in Monterey
Berkshires Retreat | Hiking & Swim | Fenced Yard
5 bedrooms, 7 beds, 3.5 bathrooms
11–16 Jul
5.0 out of 5 average rating, 45 reviews
Home in Monterey
Monterey, MA. Walk to Lake Garfield.
3 bedrooms, 4 beds, 3 bathrooms
12–17 Jul
Guest favourite
Cabin in Monterey
Amazing Berkshire Mountains Cabin
4 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
4.94 out of 5 average rating, 305 reviews
Guest favourite
Home in Monterey
Lake Garfield: New Summer Dates Open!
3 bedrooms, 5 beds, 3.5 bathrooms
11–16 Oct
4.95 out of 5 average rating, 22 reviews
Guest favourite
Home in Monterey
4 Acres | Rustic-Modern Berkshires Retreat
2 bedrooms, 4 beds, 1 bathroom
12–17 Jul
4.91 out of 5 average rating, 155 reviews
Top guest favourite
Home in Monterey
Beautiful family home, Hike, Fireplace, Sleeps 12
5 bedrooms, 7 beds, 2.5 bathrooms
29 Aug – 3 Sept
4.96 out of 5 average rating, 229 reviews
Top guest favourite
Home in Otis
Private Mountain Retreat - Near lakes/Tanglewood
4 bedrooms, 6 beds, 3 bathrooms
22–27 Jul
5.0 out of 5 average rating, 15 reviews
Cabin in Monterey
Exotic Mountain Retreat in the Berkshires.
5 bedrooms, 9 beds, 4.5 bathrooms
14–19 Jul
4.9 out of 5 average rating, 207 reviews
Top guest favourite
Barn in New Marlborough
Hartsville Barn in the Berkshires
2 bedrooms, 2 king beds, 1 bathroom
14–19 Sept
4.98 out of 5 average rating, 41 reviews
Top guest favourite
Cottage in Great Barrington
Carriage house with Chef's Kitchen, close to town
2 bedrooms, 3 beds, 1.5 bathrooms
6–11 Sept
4.93 out of 5 average rating, 150 reviews