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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
3 bedrooms, 3 beds
9–14 Sept
4.87 out of 5 average rating, 255 reviews
Guest favourite
Room in Sandisfield
Hospitality in the Berkshire Woods
1 king bed
21–26 Jul
4.94 out of 5 average rating, 158 reviews
Top guest favourite
Home in Monterey
Charming cottage w/ gorgeous views.
2 bedrooms, 2 beds
7–12 Sept
4.93 out of 5 average rating, 367 reviews
Home in New Marlborough
Konkapot River Retreat
2 bedrooms, 3 beds
23–28 Jul
Guest favourite
Home in Monterey
4 Acres | Rustic-Modern Berkshires Retreat
2 bedrooms, 4 beds
26–31 Jul
4.91 out of 5 average rating, 157 reviews
Guest favourite
Home in Monterey
Lake Garfield: New Summer Dates Open!
3 bedrooms, 5 beds
11–16 Oct
4.95 out of 5 average rating, 22 reviews
Guest favourite
Home in Monterey
Quiet Retreat on Five Acres w/views
4 bedrooms, 4 beds
24–29 Aug
5.0 out of 5 average rating, 11 reviews
Top guest favourite
Home in Monterey
Beautiful Lake Retreat
3 bedrooms, 4 beds
21–26 Aug
5.0 out of 5 average rating, 9 reviews
Guest favourite
Cabin in Monterey
Amazing Berkshire Mountains Cabin
4 bedrooms, 4 beds
23–28 Aug
4.94 out of 5 average rating, 306 reviews
Top guest favourite
Cottage in Monterey
Beaver Lodge
3 bedrooms, 3 queen beds
10–15 Sept
5.0 out of 5 average rating, 82 reviews
Top guest favourite
Chalet in Monterey
Cozy French Country Chalet
2 bedrooms, 3 beds
11–16 Sept
4.98 out of 5 average rating, 95 reviews
Guest favourite
Home in Monterey
Forest Hollow | Waterfront • Kayaks • Wood Stove
3 bedrooms, 4 beds
9–14 Sept
4.84 out of 5 average rating, 96 reviews
Home in Monterey
Monterey, MA. Walk to Lake Garfield.
3 bedrooms, 4 beds
23–28 Aug
Guest favourite
Flat in Great Barrington
King Bed, Wi-Fi, 2m Ski Resort
1 king bed
22–27 Aug
4.96 out of 5 average rating, 182 reviews
Home in Great Barrington
Modern Escape in the Woods of the Berkshires - 4br
4 bedrooms, 5 beds
8–13 Sept
4.84 out of 5 average rating, 49 reviews
Top guest favourite
Room in Great Barrington
Cozy & Convenient
1 queen bed
2–7 Aug
5.0 out of 5 average rating, 47 reviews
Top guest favourite
Room in Becket
priv. rm.#2 in forest clearing home
1 queen bed
26–31 Jul
4.81 out of 5 average rating, 331 reviews
Top guest favourite
Guest house in Stockbridge
Bitty Berkshire Bungalow
1 bedroom, 1 queen bed
18–23 Sept
4.98 out of 5 average rating, 47 reviews