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Search results; Over 1,000 homes in Monterey

Top guest favourite
Cabin in Monterey
Amazing Berkshire Mountains Cabin
4 bedrooms, 4 beds, 2 private bathrooms
14–19 Sept
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4.95 out of 5 average rating, 313 reviews
Superhost
Home in Monterey
Forget-Me-Not by AvantStay | Bold Lakefront Escape
4 bedrooms, 8 beds, 4 bathrooms
12–17 Oct
4.9 out of 5 average rating, 71 reviews
Top guest favourite
Home in Monterey
Jaw dropping mountain & lake views
4 bedrooms, 4 beds, 2 bathrooms
1–6 Nov
4.96 out of 5 average rating, 310 reviews
Top guest favourite
Home in Monterey
Berkshires Retreat | Fall Foliage | Fenced Yard
5 bedrooms, 7 beds, 3.5 bathrooms
14–19 Sept
5.0 out of 5 average rating, 49 reviews
Top guest favourite
Home in Monterey
Beautiful family home, Hike, Fireplace, Sleeps 12
5 bedrooms, 7 beds, 2.5 bathrooms
15–20 Sept
4.96 out of 5 average rating, 236 reviews
Guest favourite
Home in Monterey
Forest Hollow | Waterfront • Kayaks • Wood Stove
3 bedrooms, 4 beds, 1.5 bathrooms
14–19 Sept
4.85 out of 5 average rating, 102 reviews
Top guest favourite
Cottage in Monterey
Beaver Lodge
3 bedrooms, 3 queen beds, 1.5 bathrooms
28 Sept – 3 Oct
5.0 out of 5 average rating, 83 reviews
Cabin in Monterey
Exotic Mountain Retreat in the Berkshires.
5 bedrooms, 9 beds, 4.5 bathrooms
14–19 Sept
4.89 out of 5 average rating, 209 reviews
Guest favourite
Home in Monterey
Garfield Grounds | Lakeside • Guest Cottage • Dock
4 bedrooms, 5 beds, 3 bathrooms
14–19 Sept
4.93 out of 5 average rating, 28 reviews
Guest favourite
Home in Monterey
Bidwell Landing | Lakefront • Spacious
4 bedrooms, 5 beds, 3 bathrooms
14–19 Sept
4.88 out of 5 average rating, 112 reviews
Top guest favourite
Home in Monterey
Charming cottage w/ gorgeous views.
2 bedrooms, 2 beds, 2 bathrooms
16–21 Sept
4.93 out of 5 average rating, 373 reviews
Superhost
Cabin in Monterey
Secluded cabin with babbling brook
3 bedrooms, 3 beds, 1 bathroom
17–22 Nov
4.87 out of 5 average rating, 258 reviews
Home in Monterey
Monterey Home w/ Hot Tub, Pool & Game Room!
6 bedrooms, 10 beds, 6 bathrooms
7–12 Dec
4.85 out of 5 average rating, 47 reviews
Guest favourite
Home in Sandisfield
Waterfront oasis in heart of Berkshires
4 bedrooms, 3 beds, 3 bathrooms
14–19 Sept
4.96 out of 5 average rating, 51 reviews
Top guest favourite
Cabin in Monterey
Misty Pines Cabin | Wood Stove • Sauna
3 bedrooms, 6 beds, 3 bathrooms
21–26 Sept
5.0 out of 5 average rating, 28 reviews
Top 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, 8 reviews
Top guest favourite
Home in Monterey
Berkshires Retreat w Magic View! Beach/Swim 1 mi!
3 bedrooms, 3 beds, 2 bathrooms
11–16 Oct
4.89 out of 5 average rating, 121 reviews
Guest favourite
Home in Great Barrington
Berkshires Family Oasis with Hot Tub, Patio, Gym
4 bedrooms, 7 beds, 2.5 bathrooms
14–19 Sept
4.98 out of 5 average rating, 50 reviews
Home in Great Barrington
Modern Escape in the Woods of the Berkshires - 4br
4 bedrooms, 5 beds, 3 bathrooms
14–19 Sept
4.84 out of 5 average rating, 49 reviews