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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, 307 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, 23 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
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
Home in Monterey
Monterey, MA. Walk to Lake Garfield.
3 bedrooms, 4 beds, 3 bathrooms
23–28 Aug
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
Contemporary Modern Mountain Retreat
4 bedrooms, 8 beds, 3 bathrooms
5–10 Oct
5.0 out of 5 average rating, 5 reviews
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
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
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, 28 reviews
Top guest favourite
Barn in New Marlborough
Hartsville Barn in the Berkshires
2 bedrooms, 2 king beds, 1 bathroom
27 Oct – 1 Nov
4.98 out of 5 average rating, 43 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
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
Cottage in Great Barrington
The Cottage at The Barrington House
1 bedroom, 1 queen bed, 1 bathroom
22–27 Aug
4.94 out of 5 average rating, 214 reviews
Top guest favourite
Cabin in Great Barrington
Modern Luxury Log Cabin
4 bedrooms, 6 beds, 3 bathrooms
23–28 Aug
4.97 out of 5 average rating, 115 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
Guest favourite
Place to stay in Stockbridge
Cozy room w/private bath–near Tanglewood/Kripalu
1 bedroom, 1 bed, 1 bathroom
23–28 Aug
4.85 out of 5 average rating, 158 reviews
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