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Over 1,000 places in Plainfield

Guest favorite

Apartment in Plainfield

Sunny carriage house apartment

2 beds

May 1 – 6

$107 per night

4.95 out of 5 average rating, 237 reviews

Guest favorite

Apartment in Plainfield

Sunny, light filled loft in 1873 Colonial

1 bed

Apr 18 – 23

$123 per night

4.97 out of 5 average rating, 238 reviews

Cabin in Plainfield

Peaceful Cabin in the Woods

2 king beds

Apr 21 – 26

$215 per night

4.91 out of 5 average rating, 106 reviews

Cottage in Plainfield

Windsor Pond spacious get-away cottage

4 beds

Jun 1 – 6

$110 per night

4.8 out of 5 average rating, 40 reviews

Cabin in Plainfield

Camp on Windsor Pond- Berkshires

May 1 – 6

$199 per night

4.52 out of 5 average rating, 25 reviews

Guest favorite

Home in Plainfield

Sleeps upto 10ppl, Wi-Fi w/ fireplace

5 beds

Apr 26 – May 1

$242 per night, originally $279

4.73 out of 5 average rating, 148 reviews

Home in Plainfield

Farm House on 400 acres

6 beds

Nov 2 – 7

$150 per night

5.0 out of 5 average rating, 3 reviews

Guest favorite

Home in Ashfield

An 18th century farmhouse

2 beds

Apr 18 – 23

$150 per night

5.0 out of 5 average rating, 7 reviews

Home in Cummington

River Forest House

3 beds

May 1 – 6

$296 per night

4.82 out of 5 average rating, 55 reviews

Guest favorite

Chalet in Cummington

Berkshire A-Frame Chalet!

1 queen bed

Jun 14 – 19

$150 per night

4.86 out of 5 average rating, 101 reviews

Guest favorite

Cabin in Savoy

The Camp - 20 Minutes to Berkshire East!

1 queen bed

May 7 – 12

$99 per night

4.98 out of 5 average rating, 186 reviews

Guest favorite

Home in Ashfield

Magical, Rural Getaway in the Berkshires

6 beds

Apr 21 – 26

$140 per night

4.98 out of 5 average rating, 48 reviews

Home in Hawley

Flights End-Country Home with Babbling Brook, Pond

6 beds

Apr 18 – 23

$190 per night

4.86 out of 5 average rating, 29 reviews

Guest favorite

Cottage in Ashfield

hope house

2 beds

May 5 – 10

$155 per night

4.97 out of 5 average rating, 299 reviews

Guest favorite

Vacation home in Hawley

Retro 1970s home in the Berkshires

5 beds

Apr 18 – 23

$450 per night

5.0 out of 5 average rating, 48 reviews

Guest favorite

Home in Ashfield

Sunny Chalet Nestled in the Woods of Ashfield

5 beds

Apr 28 – May 3

$300 per night

5.0 out of 5 average rating, 75 reviews

Guest favorite

Home in Ashfield

J&J’s Retreat

3 beds

Apr 19 – 24

$350 per night

5.0 out of 5 average rating, 5 reviews

Farm stay in Ashfield

Blue House Farm and Gardens

3 beds

Apr 21 – 26

$200 per night

4.99 out of 5 average rating, 78 reviews