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Search results; Over 1,000 homes in Monterey

Guest favourite
Cabin in Monterey
Amazing Berkshire Mountains Cabin
4 bedrooms, 4 beds, 2 private bathrooms
23–28 Aug
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4.94 out of 5 average rating, 303 reviews
Superhost
Cabin in Monterey
Secluded cabin with babbling brook
4.88 out of 5 average rating, 252 reviews, 3 bedrooms, 3 beds, 1 bathroom
17–22 Aug
Superhost
Home in Monterey
Dog-Friendly Berkshires Retreat w/Fenced Yard
New place to stay, 3 bedrooms, 3 beds, 2.5 bathrooms
28 Jul – 2 Aug
Home in Monterey
Contemporary Modern Mountain Retreat
5.0 out of 5 average rating, 3 reviews, 4 bedrooms, 8 beds, 3 bathrooms
7–12 Aug
Guest favourite
Home in Monterey
Charming cottage w/ gorgeous views.
4.93 out of 5 average rating, 365 reviews, 2 bedrooms, 2 beds, 2 bathrooms
29 Aug – 3 Sept
Top guest favourite
Cottage in Monterey
Beaver Lodge
5.0 out of 5 average rating, 82 reviews, 3 bedrooms, 3 beds, 1.5 bathrooms
10–15 Sept
Guest favourite
Home in Monterey
4 Acres | Rustic-Modern Berkshires Retreat
4.91 out of 5 average rating, 155 reviews, 2 bedrooms, 4 beds, 1 bathroom
5–10 Jul
Top guest favourite
Home in Monterey
Jaw dropping mountain & lake views
4.96 out of 5 average rating, 302 reviews, 4 bedrooms, 4 beds, 2 bathrooms
16–21 Aug
Home in Monterey
Monterey, MA. Walk to Lake Garfield.
3 bedrooms, 4 beds, 3 bathrooms
12–17 Jul
Guest favourite
Home in Monterey
Lake Garfield: New Summer Dates Open!
4.95 out of 5 average rating, 22 reviews, 3 bedrooms, 5 beds, 3.5 bathrooms
6–11 Jul
Guest favourite
Home in Monterey
Forest Hollow | Waterfront • Kayaks • Wood Stove
4.84 out of 5 average rating, 95 reviews, 3 bedrooms, 4 beds, 1.5 bathrooms
30 Aug – 4 Sept
Top guest favourite
Barn in New Marlborough
Hartsville Barn in the Berkshires
4.98 out of 5 average rating, 40 reviews, 2 bedrooms, 2 beds, 1 bathroom
14–19 Sept
Superhost
Home in Monterey
Forget-Me-Not by AvantStay | Bold Lakefront Escape
4.9 out of 5 average rating, 69 reviews, 4 bedrooms, 8 beds, 4 bathrooms
15–20 Aug
Top guest favourite
Home in Monterey
Swim Lake, Hikes, Sleeps 12,
4.96 out of 5 average rating, 229 reviews, 5 bedrooms, 7 beds, 2.5 bathrooms
29 Aug – 3 Sept
Top guest favourite
Home in Monterey
Beautiful Lake Retreat
5.0 out of 5 average rating, 9 reviews, 3 bedrooms, 4 beds, 2 bathrooms
14–19 Aug
Top guest favourite
Cabin in Monterey
Misty Pines Cabin | Wood Stove • Sauna
5.0 out of 5 average rating, 18 reviews, 3 bedrooms, 6 beds, 3 bathrooms
27 Jul – 1 Aug
Guest favourite
Home in Great Barrington
Lovely house in the Berkshires
4.95 out of 5 average rating, 22 reviews, 3 bedrooms, 4 beds, 1.5 bathrooms
7–12 Sept
Guest favourite
Home in Monterey
Tranquility and Beauty at Lake Haven
5.0 out of 5 average rating, 7 reviews, 3 bedrooms, 5 beds, 2 bathrooms
6–11 Sept
Top guest favourite
Cottage in Monterey
Fully renovated! Private cottage getaway
4.97 out of 5 average rating, 32 reviews, 1 bedroom, 1 bed, 2 bathrooms
25–30 Aug