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5 Best Vacation Rentals in Osterville - Holiday Lettings - Cabins

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1,249 Vacation rentals

Vacation home in Osterville

Osterville house

3 bedrooms • 2 bathrooms • sleeps 8

from $172 / night

$1,200 / week

1 / 29

Osterville Vacation home rental

Osterville house

3 bedrooms • 4 bathrooms • sleeps 6

2 reviews

from $140 / night

$1,000 - $1,800 / week

1 / 17

Osterville Vacation home rental

Osterville house

4 bedrooms • 3 bathrooms • sleeps 8

from $1,140 / night

$7,975 / week

1 / 32

Vacation home in Osterville

Osterville house

3 bedrooms • 2 bathrooms • sleeps 8

from $373 / night

$2,605 / week

1 / 28

Home accommodation in Osterville

Osterville house

4 bedrooms • 2 bathrooms • sleeps 8

from $243 / night

$1,700 / week

1 / 25

Vacation home in Osterville

Osterville house

3 bedrooms • 3 bathrooms • sleeps 6

from $300 / night

$2,100 / week

1 / 18

Vacation home in Osterville

Osterville house

4 bedrooms • 2 bathrooms • sleeps 8

from $487 / night

$3,407 / week

1 / 16

Vacation home with swimming pool in Osterville

Osterville house

3 bedrooms • 2 bathrooms • sleeps 8

from $1,145 / night

$10,706 - $12,595 / week

1 / 65

Great rentals within 20 miles that match your search

Vacation home in West Yarmouth

West Yarmouth house

6 bedrooms • 3 bathrooms • sleeps 12

2 reviews

from $573 / night

$4,008 / week

1 / 25

Vacation home in Oak Bluffs

Oak Bluffs house

1 bedroom • 1 bathroom • sleeps 2

from $344 / night

$2,405 / week

1 / 4

Vacation private room in Oak Bluffs

Oak Bluffs private room

1 bedroom • 1 bathroom • sleeps 2

from $344 / night

$2,405 / week

1 / 6

Home rental in Falmouth

Falmouth house

7 bedrooms • 4 bathrooms • sleeps 16

from $736 / night

$5,153 / week

1 / 9

Home rental in Oak Bluffs

Oak Bluffs house

3 bedrooms • 2 bathrooms • sleeps 6

from $409 / night

$2,863 / week

1 / 13

Vacation home in Mashpee

Mashpee house

3 bedrooms • 3 bathrooms • sleeps 10

from $843 / night

$5,897 / week

1 / 13

Vacation home in Brewster

Brewster house

3 bedrooms • 2 bathrooms • sleeps 8

from $328 / night

$2,290 / week

1 / 4

Vacation condo in West Yarmouth

West Yarmouth condo

1 bedroom • 1 bathroom • sleeps 2

from $197 / night

$1,374 / week

1 / 5

Vacation home in Teaticket

Teaticket house

2 bedrooms • 1 bathroom • sleeps 5

from $225 / night

$1,575 / week

1 / 6

Yacht rental in Hyannis

Hyannis yacht

2 bedrooms • 2 bathrooms • sleeps 4

from $687 / night

$4,809 / week

1 / 4

New Seabury Vacation home rental

New Seabury house

3 bedrooms • 3 bathrooms • sleeps 10

from $802 / night

$5,611 / week

1 / 61

Vacation home in Barnstable

Barnstable house

3 bedrooms • 4 bathrooms • sleeps 8

from $1,309 / night

$9,160 / week

1 / 20

Vacation apartment with shared pool in Brewster

Brewster apartment

2 bedrooms • 2 bathrooms • sleeps 5

from $409 / night

$2,863 / week

1 / 3

Vacation home in Falmouth

Falmouth house

3 bedrooms • 2 bathrooms • sleeps 9

from $483 / night

$3,378 / week

1 / 16

Wareham Vacation home rental

Wareham house

1 bedroom • 1 bathroom • sleeps 2

from $164 / night

$1,145 / week

1 / 4

Falmouth Vacation studio rental

Falmouth studio

Studio • 1 bathroom • sleeps 4

from $373 / night

$2,605 / week

1 / 21

Hyannis Vacation condo rental

Hyannis condo

1 bedroom • 1 bathroom • sleeps 4

from $401 / night

$2,748 / week

1 / 19

Cottage rental in East Dennis

East Dennis cottage

1 bedroom • 1 bathroom • sleeps 2

from $201 / night

$1,140 / week

1 / 10

Vacation cottage in Barnstable

Barnstable cottage

2 bedrooms • 1 bathroom • sleeps 5

from $1,145 / night

$8,015 / week

1 / 15

Vacation cottage in Harwich Port

Harwich Port cottage

4 bedrooms • 5 bathrooms • sleeps 10

1 review

from $1,432 / night

$10,878 / week

1 / 17

Vacation home in West Yarmouth

West Yarmouth house

3 bedrooms • 2 bathrooms • sleeps 8

1 review

from $246 / night

$1,718 / week

1 / 11

Vacation home in Falmouth

Falmouth house

2 bedrooms • 1 bathroom • sleeps 7

5 reviews

from $172 / night

$1,145 / week

1 / 16

Vacation apartment in Edgartown

Edgartown apartment

1 bedroom • 1 bathroom • sleeps 2

1 review

from $287 / night

$2,061 / week

1 / 1

Vacation home rental

Oak Bluffs house

4 bedrooms • 2 bathrooms • sleeps 8

1 review

from $316 / night

$2,213 / week

1 / 28

Cotuit Vacation home rental

Cotuit house

6 bedrooms • 6 bathrooms • sleeps 8

from $636 / night

$4,449 / week

1 / 58

Vacation home in Oak Bluffs

Oak Bluffs house

6 bedrooms • 6 bathrooms • sleeps 10

from $1,718 / night

$12,023 / week

1 / 50

Vacation home in Waquoit

Waquoit house

3 bedrooms • 2 bathrooms • sleeps 5

from $355 / night

$2,485 / week

1 / 27

Vacation home in Oak Bluffs

Oak Bluffs house

2 bedrooms • 3 bathrooms • sleeps 8

from $582 / night

$4,072 / week

1 / 25

Vacation home rental

Hyannis house

3 bedrooms • 1 bathroom • sleeps 6

from $347 / night

$2,429 / week

1 / 24

Vacation home in Oak Bluffs

Oak Bluffs house

3 bedrooms • 3 bathrooms • sleeps 8

from $629 / night

$4,401 / week

1 / 27

Oak Bluffs Vacation home rental

Oak Bluffs house

5 bedrooms • 5 bathrooms • sleeps 10

from $757 / night

$5,298 / week

1 / 40

Vacation home in West Tisbury

West Tisbury house

4 bedrooms • 4 bathrooms • sleeps 8

from $244 / night

$1,708 / week

1 / 49