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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
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4.96 out of 5 average rating, 302 reviews
Superhost
Home in Monterey
Dog-Friendly Berkshires Retreat w/Fenced Yard
New place to stay, 3 bedrooms, 3 beds, 2.5 bathrooms
11–16 Jul
Superhost
Cabin in Monterey
Secluded cabin with babbling brook
4.87 out of 5 average rating, 253 reviews, 3 bedrooms, 3 beds, 1 bathroom
29 Jul – 3 Aug
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
Guest favourite
Home in Monterey
Charming cottage w/ gorgeous views.
4.93 out of 5 average rating, 366 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
Superhost
Home in Monterey
Lakefront Multi-Home Compound
4.73 out of 5 average rating, 11 reviews, 6 bedrooms, 10 beds, 4 bathrooms
8–13 Jul
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
30 Aug – 4 Sept
Home in Monterey
Contemporary Modern Mountain Retreat
5.0 out of 5 average rating, 4 reviews, 4 bedrooms, 8 beds, 3 bathrooms
31 Aug – 5 Sept
Cabin in Monterey
Exotic Mountain Retreat in the Berkshires.
4.9 out of 5 average rating, 206 reviews, 5 bedrooms, 9 beds, 4.5 bathrooms
10–15 Jul
Guest favourite
Cabin in Monterey
Amazing Berkshire Mountains Cabin
4.94 out of 5 average rating, 304 reviews, 4 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
Guest favourite
Home in Great Barrington
Lovely house in the Berkshires
4.96 out of 5 average rating, 23 reviews, 3 bedrooms, 4 beds, 1.5 bathrooms
7–12 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
12–17 Jul
Home in Monterey
Monterey, MA. Walk to Lake Garfield.
3 bedrooms, 4 beds, 3 bathrooms
12–17 Jul
Top guest favourite
Home in Monterey
Berkshires Retreat | Hiking & Swim | Fenced Yard
5.0 out of 5 average rating, 44 reviews, 5 bedrooms, 7 beds, 3.5 bathrooms
11–16 Jul
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
Top guest favourite
Cabin in Sandisfield
Berkshires Cabin in Woods with Mountain Views
4.98 out of 5 average rating, 131 reviews, 3 bedrooms, 3 beds, 1.5 bathrooms
7–12 Jul
Home in Great Barrington
Cottage by the Lake | Hiking, Skiing & Attractions
New place to stay, 2 bedrooms, 4 beds, 1 bathroom
24–29 Aug
Home in Great Barrington
Full Moon Farm
3 bedrooms, 3 beds, 1 bathroom
9–14 Jul