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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, 305 reviews
Superhost
Cabin in Monterey
Secluded cabin with babbling brook
4.87 out of 5 average rating, 255 reviews, 3 bedrooms, 3 beds, 1 bathroom
9–14 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
7–12 Sept
Guest favourite
Home in Monterey
4 Acres | Rustic-Modern Berkshires Retreat
4.91 out of 5 average rating, 158 reviews, 2 bedrooms, 4 beds, 1 bathroom
1–6 Aug
Top guest favourite
Home in Monterey
Beautiful Lake Retreat
5.0 out of 5 average rating, 9 reviews, 3 bedrooms, 4 beds, 2 bathrooms
21–26 Aug
Guest favourite
Cabin in Monterey
Amazing Berkshire Mountains Cabin
4.94 out of 5 average rating, 307 reviews, 4 bedrooms, 4 beds, 2 bathrooms
23–28 Aug
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
Top guest favourite
Chalet in Monterey
Cozy French Country Chalet
4.98 out of 5 average rating, 95 reviews, 2 bedrooms, 3 beds, 1 bathroom
11–16 Sept
Guest favourite
Home in Monterey
Lake Garfield: New Summer Dates Open!
4.96 out of 5 average rating, 23 reviews, 3 bedrooms, 5 beds, 3.5 bathrooms
11–16 Oct
Guest favourite
Room in Sandisfield
Hospitality in the Berkshire Woods
4.94 out of 5 average rating, 158 reviews, 1 king bed, 1.5 bathrooms
9–14 Aug
Top guest favourite
Cabin in Monterey
Misty Pines Cabin | Wood Stove • Sauna
5.0 out of 5 average rating, 21 reviews, 3 bedrooms, 6 beds, 3 bathrooms
10–15 Aug
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
Top guest favourite
Room in Great Barrington
Cozy & Convenient
5.0 out of 5 average rating, 47 reviews, 1 queen bed, 1 bathroom
2–7 Aug
Superhost
Home in Monterey
Dog-Friendly Berkshires Retreat w/Fenced Yard
New place to stay, 3 bedrooms, 3 beds, 2.5 bathrooms
6–11 Sept
Guest favourite
Cottage in New Marlborough
Berkshire Country Cottage A Perfect Get-Away
4.88 out of 5 average rating, 52 reviews, 1 bedroom, 3 beds, 1 bathroom
5–10 Aug
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
9–14 Sept
Top guest favourite
Barn in Monterey
Scribe's Stable | A/C • Screened Porch • Sleeps 6
4.95 out of 5 average rating, 64 reviews, 2 bedrooms, 4 beds, 1 bathroom
13–18 Aug
Home in Monterey
Monterey, MA. Walk to Lake Garfield.
3 bedrooms, 4 beds, 3 bathrooms
23–28 Aug
Cottage in Monterey
Monterey Haven < 1/2 Mi to Lake Garfield w/ Kayaks
4.81 out of 5 average rating, 16 reviews, 3 bedrooms, 3 beds, 1 bathroom
2–7 Aug