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Best Boston Apartments on Holiday Lettings - Condos

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1 Vacation rentals

Great rentals within 20 miles that match your search

Ski condo to rent in Hancock

Hancock condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 6

from $260 / night

$1,489 / week

1 / 39

Great rentals within 20 miles that match your search

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Vacation cave house with golf nearby in Marlborough

Marlborough cave house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

1 filter does not match: Skiing – property near ski resort

from $12 / night

$23 - $344 / week

1 / 4

Great rentals within 20 miles that match your search

Vacation home in Southampton

Southampton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

1 filter does not match: Skiing – property near ski resort

from $540 / night

$3,779 / week

1 / 17

Great rentals within 20 miles that match your search

West Harwich Vacation home rental

West Harwich house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 filter does not match: Skiing – property near ski resort

from $115 / night

$573 - $2,634 / week

1 / 25

Great rentals within 20 miles that match your search

Vacation cottage in Sag Harbor

Sag Harbor cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 filter does not match: Skiing – property near ski resort

from $687 / night

$4,329 / week

1 / 15

Great rentals within 20 miles that match your search

Vacation home in Southampton

Southampton house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 9

1 filter does not match: Skiing – property near ski resort

from $1,718 / night

$12,023 / week

1 / 83

Great rentals within 20 miles that match your search

Conway ski apartment to rent.

Conway apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 3

1 filter does not match: Trampoline

from $196 / night

$1,371 / week

1 / 9

Great rentals within 20 miles that match your search

East Burke ski condo to rent.

East Burke condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

1 filter does not match: Trampoline

from $401 / night

$2,290 - $3,092 / week

1 / 11

Great rentals within 20 miles that match your search

Ski home to rent in Killington

Killington house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

1 filter does not match: Trampoline

from $859 / night

$6,012 / week

1 / 23

Great rentals within 20 miles that match your search

Ski home to rent in South Londonderry

South Londonderry house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

1 filter does not match: Trampoline

from $1,444 / night

$10,107 / week

1 / 24

Great rentals within 20 miles that match your search

Bondville ski home to rent.

Bondville house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 15

1 filter does not match: Trampoline

from $286 / night

$1,996 / week

1 / 32

Great rentals within 20 miles that match your search

Ski condo to rent in Ludlow

Ludlow condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 filter does not match: Trampoline

from $229 / night

$1,603 / week

1 / 23

Great rentals within 20 miles that match your search

Jeffersonville ski condo to rent.

Jeffersonville condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

1 filter does not match: Trampoline

from $753 / night

$5,266 / week

1 / 40

Great rentals within 20 miles that match your search

Killington ski home to rent.

Killington house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 8

1 filter does not match: Trampoline

from $544 / night

$3,808 / week

1 / 14

Great rentals within 20 miles that match your search

Naples ski home to rent.

Naples house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 filter does not match: Trampoline

from $322 / night

$2,253 / week

1 / 72

Great rentals within 20 miles that match your search

Ludlow ski home to rent.

Ludlow house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 13

1 filter does not match: Trampoline

from $1,374 / night

$5,840 / week

1 / 20

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

1 filter does not match: Trampoline

from $109 / night

$630 / week

1 / 23

Great rentals within 20 miles that match your search

Ski condo to rent in Wilmington

Wilmington condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 filter does not match: Trampoline

from $81 / night

$561 / week

1 / 7

Great rentals within 20 miles that match your search

Newry ski home to rent.

Newry house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 16

1 filter does not match: Trampoline

from $1,598 / night

$11,181 / week

1 / 42

Great rentals within 20 miles that match your search

Ski condo to rent in Killington

Killington condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Trampoline

from $338 / night

$2,365 / week

1 / 36

Great rentals within 20 miles that match your search

Cambridge ski condo to rent.

Cambridge condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 8

1 filter does not match: Trampoline

from $452 / night

$3,158 / week

1 / 39

Great rentals within 20 miles that match your search

Bondville ski condo to rent.

Bondville condo

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 15

1 filter does not match: Trampoline

from $171 / night

$1,195 / week

1 / 15

Great rentals within 20 miles that match your search

Ski condo to rent in Bartlett

Bartlett condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 12

1 filter does not match: Trampoline

from $401 / night

$2,806 / week

1 / 22

Great rentals within 20 miles that match your search

Campton ski home to rent.

Campton house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 12

1 filter does not match: Trampoline

from $974 / night

$5,926 / week

1 / 32

Great rentals within 20 miles that match your search

Ski home to rent in Lincoln

Lincoln house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 14

1 filter does not match: Trampoline

from $801 / night

$5,603 / week

1 / 27

Great rentals within 20 miles that match your search

Ski townhouse to rent in Peru

Peru townhouse

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

1 filter does not match: Trampoline

from $338 / night

$2,365 / week

1 / 20

Great rentals within 20 miles that match your search

Ski townhouse to rent in Lincoln

Lincoln townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 7

1 filter does not match: Trampoline

from $430 / night

$3,006 / week

1 / 17

Great rentals within 20 miles that match your search

Ski manor house to rent in Middletown

Middletown manor house

  • 9 bedrooms
  • 10 bathrooms
  • sleeps 12

1 filter does not match: Trampoline

from $1,002 / night

$5,725 / week

1 / 9

Great rentals within 20 miles that match your search

Ski townhouse to rent in Dover

Dover townhouse

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 filter does not match: Trampoline

from $229 / night

$1,603 / week

1 / 22

Great rentals within 20 miles that match your search

Ski home to rent in Killington

Killington house

  • 6 bedrooms
  • 3 bathrooms
  • sleeps 10

1 filter does not match: Trampoline

from $1,088 / night

$7,615 / week

1 / 53

Great rentals within 20 miles that match your search

Raymond ski home to rent.

Raymond house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 filter does not match: Trampoline

from $129 / night

$898 / week

1 / 42

Great rentals within 20 miles that match your search

Raymond ski home to rent.

Raymond house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 filter does not match: Trampoline

from $81 / night

$561 / week

1 / 23

Great rentals within 20 miles that match your search

Raymond ski studio to rent.

Raymond studio

  • Studio
  • 1 bathroom
  • sleeps 3

1 filter does not match: Trampoline

from $81 / night

$561 / week

1 / 27

Great rentals within 20 miles that match your search

Ski home to rent in Stratton Mountain

Stratton Mountain house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

1 filter does not match: Trampoline

from $201 / night

$1,088 / week

1 / 9

Great rentals within 20 miles that match your search

Ski home to rent in Lincoln

Lincoln house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Trampoline

from $258 / night

$1,623 / week

1 / 19

Great rentals within 20 miles that match your search

Ski townhouse to rent in Killington

Killington townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Trampoline

from $113 / night

$738 - $8,749 / week

1 / 22

Great rentals within 20 miles that match your search

Ski condo to rent in Killington

Killington condo

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Trampoline

from $160 / night

$1,114 / week

1 / 21

Great rentals within 20 miles that match your search

Killington ski townhouse to rent.

Killington townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Trampoline

from $113 / night

$738 - $9,050 / week

1 / 22

Great rentals within 20 miles that match your search

Ski townhouse to rent in Killington

Killington townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Trampoline

from $113 / night

$738 - $8,817 / week

1 / 22

Great rentals within 20 miles that match your search

Ski townhouse to rent in Killington

Killington townhouse

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Trampoline

from $113 / night

$738 - $8,448 / week

1 / 22