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Search results; Over 1,000 homes in Monterey

Top guest favourite
Chalet in Monterey
Cozy French Country Chalet
2 bedrooms, 3 beds, 1 private bathroom
11–16 Sept
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4.98 out of 5 average rating, 94 reviews
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
Superhost
Cabin in Monterey
Secluded cabin with babbling brook
4.87 out of 5 average rating, 254 reviews, 3 bedrooms, 3 beds, 1 bathroom
28 Aug – 2 Sept
Top guest favourite
Home in Monterey
Jaw dropping mountain & lake views
4.96 out of 5 average rating, 303 reviews, 4 bedrooms, 4 beds, 2 bathrooms
16–21 Aug
Guest favourite
Home in Great Barrington
Lovely house in the Berkshires
4.96 out of 5 average rating, 24 reviews, 3 bedrooms, 4 beds, 1.5 bathrooms
7–12 Sept
Top guest favourite
Home in Monterey
Charming cottage w/ gorgeous views.
4.93 out of 5 average rating, 367 reviews, 2 bedrooms, 2 beds, 2 bathrooms
29 Aug – 3 Sept
Guest favourite
Home in Monterey
Forest Hollow | Waterfront • Kayaks • Wood Stove
4.84 out of 5 average rating, 96 reviews, 3 bedrooms, 4 beds, 1.5 bathrooms
8–13 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
Home in Monterey
Contemporary Modern Mountain Retreat
5.0 out of 5 average rating, 4 reviews, 4 bedrooms, 8 beds, 3 bathrooms
28 Sept – 3 Oct
Cabin in Monterey
Exotic Mountain Retreat in the Berkshires.
4.9 out of 5 average rating, 207 reviews, 5 bedrooms, 9 beds, 4.5 bathrooms
16–21 Jul
Guest favourite
Home in New Marlborough
Best Berkshire Cottage
5.0 out of 5 average rating, 9 reviews, 3 bedrooms, 4 beds, 1.5 bathrooms
15–20 Jul
Guest favourite
Cabin in Monterey
Amazing Berkshire Mountains Cabin
4.94 out of 5 average rating, 306 reviews, 4 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
Top guest favourite
Home in Monterey
Berkshires Retreat | Hiking & Swim | Fenced Yard
5.0 out of 5 average rating, 46 reviews, 5 bedrooms, 7 beds, 3.5 bathrooms
28 Jul – 2 Aug
Top guest favourite
Home in Otis
Private Mountain Retreat - Near lakes/Tanglewood
5.0 out of 5 average rating, 15 reviews, 4 bedrooms, 6 beds, 3 bathrooms
22–27 Jul
Home in Monterey
Monterey, MA. Walk to Lake Garfield.
3 bedrooms, 4 beds, 3 bathrooms
19–24 Jul
Guest favourite
Home in Tyringham
Treetop Hideaway in Tyringham
4.82 out of 5 average rating, 136 reviews, 4 bedrooms, 4 beds, 2.5 bathrooms
13–18 Jul
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
15–20 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
11–16 Oct
Top guest favourite
Home in New Marlborough
Berkshire Retreat at Cantina 229
5.0 out of 5 average rating, 12 reviews, 5 bedrooms, 5 beds, 3.5 bathrooms
20–25 Jul