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Search results; Over 1,000 homes in Plainfield

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Top guest favourite
Flat in Plainfield
Sunny, light filled loft in 1873 Colonial
1 bedroom, 1 bed, 1 shared bathroom
20–25 Sept
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4.97 out of 5 average rating, 310 reviews
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Home in Plainfield
Berkshire Forest Getaway
3 bedrooms, 4 beds, 1.5 bathrooms
21–26 Sept
5.0 out of 5 average rating, 9 reviews
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Flat in Plainfield
Sunny carriage house apartment
1 bedroom, 2 beds, 1 bathroom
27 Sept – 2 Oct
4.95 out of 5 average rating, 305 reviews
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Cabin in Plainfield
Peaceful Lakeside Cabin
1 bed, 1 bathroom
23–28 Jul
4.96 out of 5 average rating, 27 reviews
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Home in Ashfield
An 18th century farmhouse
2 bedrooms, 2 beds, 1 bathroom
20–25 Sept
4.97 out of 5 average rating, 109 reviews
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Home in Ashfield
J&J’s Retreat
3 bedrooms, 3 beds, 2 bathrooms
18–23 Sept
5.0 out of 5 average rating, 35 reviews
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Home in Ashfield
Cocoa House
3 bedrooms, 6 beds, 1.5 bathrooms
17–22 Sept
5.0 out of 5 average rating, 28 reviews
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Home in Worthington
Extraordinary Berkshires Estate & Carriage House
9 bedrooms, 21 beds, 7.5 bathrooms
26–31 Oct
5.0 out of 5 average rating, 20 reviews
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Home in Cummington
Camp Emerson
2 bedrooms, 2 queen beds, 1 bathroom
20–25 Sept
5.0 out of 5 average rating, 16 reviews
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Home in Worthington
Chateau Worthington - Luxury Retreat w/ Indoor Pool
6 bedrooms, 17 beds, 6.5 bathrooms
26–31 Oct
5.0 out of 5 average rating, 23 reviews
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Home in Cummington
River-front home in Berkshire hills w/tennis court
4 bedrooms, 6 beds, 3 bathrooms
18–23 Sept
5.0 out of 5 average rating, 19 reviews
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Guest suite in Charlemont
The Corner of Main and South St. 2 bedroom Suite.
2 bedrooms, 2 beds, 1 bathroom
12–17 Oct
5.0 out of 5 average rating, 60 reviews
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Home in Charlemont
Last minute cancellation! Got time to raft, hike?
4 bedrooms, 5 beds, 2 bathrooms
18–23 Sept
4.96 out of 5 average rating, 96 reviews
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Home in Chester
Riverhouse! Peak Foliage October 10-24
2 bedrooms, 5 beds, 1 bathroom
18–23 Oct
4.92 out of 5 average rating, 13 reviews
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Home in Cummington
Beautiful Secluded Country House
6 bedrooms, 11 beds, 3 bathrooms
28 Sept – 3 Oct
4.91 out of 5 average rating, 126 reviews
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Home in Charlemont
Tall Pines Rental | Pet Friendly | Fire Pit | Yard
3 bedrooms, 6 beds, 2 bathrooms
17–22 Sept
4.96 out of 5 average rating, 80 reviews
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Home in Pittsfield
Cozy Lake Cottage
2 bedrooms, 2 beds, 1.5 bathrooms
19–24 Sept
5.0 out of 5 average rating, 6 reviews
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Home in Hawley
Stump Sprouts Lodge
7 bedrooms, 18 beds, 3.5 bathrooms
18–23 Sept
4.96 out of 5 average rating, 46 reviews
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Flat in Greenfield
Treetop Haven
2 bedrooms, 3 beds, 1 bathroom
25–30 Oct
4.92 out of 5 average rating, 50 reviews