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Search results; Over 1,000 homes in Monterey

Top guest favourite
Home in Monterey
Berkshires Retreat w Magic View! Beach/Swim 1 mi!
3 bedrooms, 3 beds, 2 private bathrooms
9–14 Sept
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4.89 out of 5 average rating, 121 reviews
Superhost
Cabin in Monterey
Secluded cabin with babbling brook
3 bedrooms, 3 beds, 1 bathroom
9–14 Sept
4.87 out of 5 average rating, 256 reviews
Top guest favourite
Cabin in Monterey
Misty Pines Cabin | Wood Stove • Sauna
3 bedrooms, 6 beds, 3 bathrooms
10–15 Aug
5.0 out of 5 average rating, 21 reviews
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, 305 reviews
Top guest favourite
Home in Monterey
Charming cottage w/ gorgeous views.
2 bedrooms, 2 beds, 2 bathrooms
7–12 Sept
4.93 out of 5 average rating, 369 reviews
Home in Monterey
Monterey, MA. Walk to Lake Garfield.
3 bedrooms, 4 beds, 3 bathrooms
23–28 Aug
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, 308 reviews
Home in Monterey
Contemporary Modern Mountain Retreat
4 bedrooms, 8 beds, 3 bathrooms
5–10 Oct
5.0 out of 5 average rating, 5 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
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
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, 83 reviews
Superhost
Home in Monterey
Dog-Friendly Berkshires Retreat w/Fenced Yard
3 bedrooms, 3 beds, 2.5 bathrooms
6–11 Sept
New place to stay
Superhost
Home in Monterey
Forget-Me-Not by AvantStay | Bold Lakefront Escape
4 bedrooms, 8 beds, 4 bathrooms
7–12 Sept
4.9 out of 5 average rating, 70 reviews
Top guest favourite
Barn in Monterey
Scribe's Stable | A/C • Screened Porch • Sleeps 6
2 bedrooms, 4 beds, 1 bathroom
24–29 Aug
4.95 out of 5 average rating, 64 reviews
Guest favourite
Home in Monterey
4 Acres | Rustic-Modern Berkshires Retreat
2 bedrooms, 4 beds, 1 bathroom
15–20 Aug
4.91 out of 5 average rating, 159 reviews
Top guest favourite
Home in Monterey
Quiet Retreat on Five Acres w/views
4 bedrooms, 4 beds, 4 bathrooms
24–29 Aug
5.0 out of 5 average rating, 13 reviews
Guest favourite
Home in Monterey
Tranquility and Beauty at Lake Haven
3 bedrooms, 5 beds, 2 bathrooms
6–11 Sept
5.0 out of 5 average rating, 8 reviews
Guest favourite
Home in Great Barrington
Lovely house in the Berkshires
3 bedrooms, 4 beds, 1.5 bathrooms
7–12 Sept
4.93 out of 5 average rating, 27 reviews
Top guest favourite
Cottage in Great Barrington
Carriage house with Chef's Kitchen, close to town
2 bedrooms, 3 beds, 1.5 bathrooms
25–30 Oct
4.93 out of 5 average rating, 154 reviews