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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

Vacation villa in Amagansett

Amagansett villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 10

from $1,603 / night

$9,618 - $11,221 / week

1 / 38

Great rentals within 20 miles that match your search

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Vacation home in East Hampton

East Hampton house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 9

1 filter does not match: Property type

from $1,145 / night

$8,015 / week

1 / 23

Great rentals within 20 miles that match your search

Vacation home with golf nearby in East Hampton

East Hampton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Property type

from $2,519 / night

$14,313 / week

1 / 26

Great rentals within 20 miles that match your search

Vacation home in East Hampton

East Hampton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

1 filter does not match: Property type

from $1,064 / night

$7,443 / week

1 / 20

Great rentals within 20 miles that match your search

Vacation home with golf nearby in Oak Bluffs

Oak Bluffs house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 19

1 filter does not match: Property type

from $6,870 / night

$48,090 / week

1 / 49

Great rentals within 20 miles that match your search

East Hampton Vacation home rental

East Hampton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Property type

from $900 / night

$6,298 / week

1 / 17

Great rentals within 20 miles that match your search

Villa rental in Sosua with swimming pool

Sosua villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

1 filter does not match: Private outdoor pool (heated)

from $161 / night

$1,123 / week

1 / 12

Great rentals within 20 miles that match your search

Home rental in Truro

Truro house

  • 8 bedrooms
  • 6 bathrooms
  • sleeps 20

1 filter does not match: Property type

from $3,435 / night

$22,900 / week

1 / 44

Great rentals within 20 miles that match your search

Vacation villa rental

Belmont villa

  • 10 bedrooms
  • 4 bathrooms
  • sleeps 25

1 filter does not match: Private outdoor pool (heated)

from $2,462 / night

$14,313 / week

1 / 36

Great rentals within 20 miles that match your search

Vacation home in Amagansett

Amagansett house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 filter does not match: Property type

from $1,145 / night

$8,931 / week

1 / 23

Great rentals within 20 miles that match your search

Vacation manor house in Amagansett

Amagansett manor house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

1 filter does not match: Property type

from $1,374 / night

$9,618 / week

1 / 24

Great rentals within 20 miles that match your search

Villa rental in Newburyport

Newburyport villa

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 16

1 filter does not match: Private outdoor pool (heated)

from $1,137 / night

$7,958 - $8,920 / week

1 / 35

Great rentals within 20 miles that match your search

Vacation condo with indoor pool in Hampton

Hampton condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 filter does not match: Property type

from $269 / night

$1,884 / week

1 / 15

Great rentals within 20 miles that match your search

Amagansett Vacation home rental

Amagansett house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

1 filter does not match: Property type

from $1,309 / night

$9,160 / week

1 / 11

Great rentals within 20 miles that match your search

Vacation home in East Hampton

East Hampton house

  • 7 bedrooms
  • 9 bathrooms
  • sleeps 12

1 filter does not match: Property type

from $4,908 / night

$34,350 / week

1 / 38

Great rentals within 20 miles that match your search

Montauk Vacation manor house rental

Montauk manor house

  • 5 bedrooms
  • 8 bathrooms
  • sleeps 10

1 filter does not match: Property type

from $17,175 / night

$120,225 / week

1 / 30

Great rentals within 20 miles that match your search

Vacation farmhouse in East Hampton

East Hampton farmhouse

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

1 filter does not match: Property type

from $1,088 / night

$7,615 / week

1 / 24

Great rentals within 20 miles that match your search

Orleans Vacation home rental

Orleans house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

1 filter does not match: Property type

from $1,309 / night

$9,160 / week

1 / 17

Great rentals within 20 miles that match your search

Vacation condo rental

Hampton condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 filter does not match: Property type

from $269 / night

$1,884 / week

1 / 12

Great rentals within 20 miles that match your search

Vacation villa in Barnstable

Barnstable villa

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 10

1 filter does not match: Private outdoor pool (heated)

from $516 / night

$3,664 - $6,813 / week

1 / 24

Great rentals within 20 miles that match your search

Vacation villa in Barnstable

Barnstable villa

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

1 filter does not match: Private outdoor pool (heated)

from $572 / night

$4,008 - $7,214 / week

1 / 26

Great rentals within 20 miles that match your search

Home rental in Nantucket

Nantucket house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

1 filter does not match: Property type

from $3,206 / night

$22,442 / week

1 / 22

Great rentals within 20 miles that match your search

Vacation villa in Brewster

Brewster villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Private outdoor pool (heated)

from $295 / night

$2,059 / week

1 / 17

Great rentals within 20 miles that match your search

Vacation home in Centerville

Centerville house

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 14

1 filter does not match: Property type

from $1,712 / night

$13,128 / week

1 / 27

Great rentals within 20 miles that match your search

Amagansett Vacation home rental

Amagansett house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

1 filter does not match: Property type

from $1,603 / night

$11,221 / week

1 / 15

Great rentals within 20 miles that match your search

Vacation home in East Hampton

East Hampton house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

1 filter does not match: Property type

from $1,918 / night

$13,426 / week

1 / 13

Great rentals within 20 miles that match your search

Vacation home with indoor pool in Amagansett

Amagansett house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Property type

from $1,088 / night

$4,008 / week

1 / 6

Great rentals within 20 miles that match your search

Vacation villa in Harwich Center

Harwich Center villa

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

1 filter does not match: Private outdoor pool (heated)

from $550 / night

$3,848 / week

1 / 26

Great rentals within 20 miles that match your search

Vacation villa in Newport

Newport villa

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Private outdoor pool (heated)

from $360 / night

$2,519 / week

1 / 4

Great rentals within 20 miles that match your search

Vacation home in West Harwich

West Harwich house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Property type

from $516 / night

$1,145 - $3,435 / week

1 / 40

Great rentals within 20 miles that match your search

Vacation home in Nantucket

Nantucket house

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

1 filter does not match: Property type

from $3,435 / night

$22,671 / week

1 / 33

Great rentals within 20 miles that match your search

Vacation home with swimming pool in East Hampton

East Hampton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Property type

from $343 / night

$2,397 / week

1 / 13

Great rentals within 20 miles that match your search

Vacation home with golf nearby in Falmouth

Falmouth house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 10

1 filter does not match: Property type

from $687 / night

$4,580 / week

1 / 17

Great rentals within 20 miles that match your search

Vacation home in Montauk

Montauk house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 9

1 filter does not match: Property type

from $687 / night

$8,588 - $17,862 / week

1 / 78

Great rentals within 20 miles that match your search

Vacation home in Worcester

Worcester house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 5

1 filter does not match: Property type

from $172 / night

$1,203 / week

1 / 20

Great rentals within 20 miles that match your search

Vacation villa accommodation

Norwich villa

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

1 filter does not match: Private outdoor pool (heated)

from $172 / night

$1,203 / week

1 / 24

Great rentals within 20 miles that match your search

Vacation home in East Hampton

East Hampton house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

1 filter does not match: Property type

from $1,374 / night

$9,618 / week

1 / 20

Great rentals within 20 miles that match your search

Vacation log cabin in Ogunquit

Ogunquit log cabin

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

1 filter does not match: Property type

from $360 / night

$2,517 / week

1 / 22

Great rentals within 20 miles that match your search

Vacation cottage with shared pool in Newbury

Newbury cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

1 filter does not match: Property type

from $127 / night

$1,957 - $2,383 / week

1 / 42

Great rentals within 20 miles that match your search

Vacation home in East Hampton

East Hampton house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

1 filter does not match: Property type

from $659 / night

$4,609 / week

1 / 15