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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
Home in Monterey
Charming cottage w/ gorgeous views.
2 bedrooms, 2 beds, 2 bathrooms
7–12 Sept
4.93 out of 5 average rating, 368 reviews
Top guest favourite
Home in Monterey
Beautiful Lake Retreat
3 bedrooms, 4 beds, 2 bathrooms
21–26 Aug
5.0 out of 5 average rating, 9 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
Guest favourite
Home in Monterey
4 Acres | Rustic-Modern Berkshires Retreat
2 bedrooms, 4 beds, 1 bathroom
2–7 Aug
4.91 out of 5 average rating, 158 reviews
Top guest favourite
Barn in Monterey
Scribe's Stable | A/C • Screened Porch • Sleeps 6
2 bedrooms, 4 beds, 1 bathroom
16–21 Aug
4.95 out of 5 average rating, 64 reviews
Guest favourite
Flat in Great Barrington
King Bed|ADA ROOM|2m Ski Resort
1 king bed, 1 bathroom
2–7 Aug
4.89 out of 5 average rating, 66 reviews
Guest favourite
Cottage in New Marlborough
Berkshire Country Cottage A Perfect Get-Away
1 bedroom, 3 beds, 1 bathroom
9–14 Aug
4.88 out of 5 average rating, 52 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
Room in Great Barrington
Cozy & Convenient
1 queen bed, 1 bathroom
2–7 Aug
5.0 out of 5 average rating, 49 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, 307 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
Guest favourite
Home in Monterey
Bidwell Landing | Lakefront • Spacious
4 bedrooms, 5 beds, 3 bathrooms
7–12 Sept
4.89 out of 5 average rating, 109 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
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
Top guest favourite
Chalet in Monterey
Cozy French Country Chalet
2 bedrooms, 3 beds, 1 bathroom
11–16 Sept
4.98 out of 5 average rating, 95 reviews
Guest favourite
Home in Monterey
Lake Garfield: New Summer Dates Open!
3 bedrooms, 5 beds, 3.5 bathrooms
11–16 Oct
4.96 out of 5 average rating, 23 reviews
Guest favourite
Room in Sandisfield
Hospitality in the Berkshire Woods
1 king bed, 1.5 bathrooms
23–28 Aug
4.94 out of 5 average rating, 159 reviews