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> North America
> United States
> Massachusetts
> Hampshire County

Vacation homes - vacation rentals

Price per day

$1 $750 -

Bedrooms

Property rating (out of 5)
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  • 4 and above
  • 3 and above
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Filtered properties are rated either by Tripadvisor Vacation Rentals users, or by Vrbo users. Both rating systems are separate, and are depicted differently as shown in the key above. Tripadvisor performs checks on its reviews. Holiday Lettings and companies under Tripadvisor Group do not check Vrbo reviews.
Property type
  • Apartment (3)
  • Villa (1)
  • Cottage (3)
  • House (16)
  • Condo (1)
  • Log cabin (2)
  • B&B (1)

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27 Vacation rentals

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Ceiling Fans

Great rentals within 20 miles that match your search

Vacation home in Becket

Becket house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4
13 reviews

from $171 / night

$1,140 / week

1 / 13

Great rentals within 20 miles that match your search

Vacation home rental

Lakeville house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 9
1 review

from $687 / night

$2,863 / week

1 / 13

Great rentals within 20 miles that match your search

Cottage rental in Salisbury

Salisbury cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4
1 review

from $207 / night

$1,443 / week

1 / 37

Great rentals within 20 miles that match your search

Savoy Vacation home rental

Savoy house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4
9 reviews

from $229 / night

$1,374 / week

1 / 6

Great rentals within 20 miles that match your search

Log cabin rental in Hillsdale

Hillsdale log cabin

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6
22 reviews

from $229 / night

$1,203 / week

1 / 31

Great rentals within 20 miles that match your search

Vacation home in Housatonic

Housatonic house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

from $682 / night

$3,779 / week

1 / 23

Great rentals within 20 miles that match your search

Vacation home with golf nearby in Lee

Lee house

  • 5 bedrooms
  • 6 bathrooms
  • sleeps 9
6 reviews

from $818 / night

$5,725 / week

1 / 18

Great rentals within 20 miles that match your search

Vacation cottage rental

Great Barrington cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 3
24 reviews

from $274 / night

$1,831 / week

1 / 18

Great rentals within 20 miles that match your search

Petersburg Vacation home rental

Petersburg house

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 7

from $338 / night

$2,247 - $2,447 / week

1 / 68

Great rentals within 20 miles that match your search

Vacation home in Stephentown

Stephentown house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

from $687 / night

$2,863 - $3,344 / week

1 / 4

Great rentals within 20 miles that match your search

Vacation home rental

Stockbridge house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5
1 review

from $327 / night

$2,290 / week

1 / 20

Great rentals within 20 miles that match your search

Vacation condo in Hancock

Hancock condo

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

from $258 / night

$1,804 / week

1 / 14

Great rentals within 20 miles that match your search

Vacation home in Webster

Webster house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 10

from $373 / night

$2,519 / week

1 / 41

Great rentals within 20 miles that match your search

Ski b&b to rent in Stephentown

Stephentown b&b

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6
2 reviews

from $109 / night

$630 / week

1 / 23

Great rentals within 20 miles that match your search

East Chatham Vacation home rental

East Chatham house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

from $1,030 / night

$7,206 / week

1 / 42

Great rentals within 20 miles that match your search

Vacation home in Ashley Falls

Ashley Falls house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

from $915 / night

$6,404 / week

1 / 46

Great rentals within 20 miles that match your search

Vacation home in Hinsdale

Hinsdale house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

from $218 / night

$1,168 - $1,248 / week

1 / 10

Great rentals within 20 miles that match your search

Hillsdale Vacation home rental

Hillsdale house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

from $281 / night

$1,718 / week

1 / 13

Great rentals within 20 miles that match your search

Stockbridge Vacation home rental

Stockbridge house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

from $802 / night

$2,806 - $4,729 / week

1 / 19

Great rentals within 20 miles that match your search

Vacation home rental

Shelburne Falls house

  • 7 bedrooms
  • 3 bathrooms
  • sleeps 14
9 reviews

from $573 / night

$3,321 / week

1 / 11

Great rentals within 20 miles that match your search

Vacation apartment in Winchester

Winchester apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6
4 reviews

from $144 / night

$848 / week

1 / 24

Great rentals within 20 miles that match your search

Charlton Vacation apartment rental

Charlton apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

from $247 / night

$1,724 / week

1 / 36

Great rentals within 20 miles that match your search

Vacation log cabin rental

Hillsdale log cabin

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 13
1 review

from $487 / night

$1,890 - $2,090 / week

1 / 18

Great rentals within 20 miles that match your search

Vacation cottage in Hinsdale

Hinsdale cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

from $287 / night

$1,718 / week

1 / 29

Great rentals within 20 miles that match your search

Vacation apartment in East Otis

East Otis apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4
1 review

from $126 / night

$802 / week

1 / 20

Great rentals within 20 miles that match your search

Lanesborough Vacation home rental

Lanesborough house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 15
3 reviews

from $795 / night

$4,574 / week

1 / 18

Great rentals within 20 miles that match your search

Vacation villa rental

Charlton villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

from $401 / night

$2,519 / week

1 / 22

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