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Holiday Houses in Osterville

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1,781 Holiday homes

271 Eel River Road

Osterville house

8 bedrooms / 8 bathrooms / sleeps 20

from £1,436 / night

£10,052 - £12,565 / week

44 Sunset Lane

Osterville house

3 bedrooms / 3 bathrooms / sleeps 6

from £329 / night

£2,298 / week

71 Sand Point Road

Osterville house

5 bedrooms / 5 bathrooms / sleeps 10

from £2,052 / night

£14,360 / week

146 Hollingsworth Road

Osterville house

4 bedrooms / 3 bathrooms / sleeps 8

1

from £257 / night

£1,795 / week

14 Indian Trail

Osterville house

5 bedrooms / 5 bathrooms / sleeps 8

from £2,052 / night

£14,360 / week

48 Pine Lane

Osterville house

3 bedrooms / 2 bathrooms / sleeps 8

from £257 / night

£1,795 - £2,298 / week

77 Robbins Street

Osterville house

5 bedrooms / 3 bathrooms / sleeps 12

1

from £359 / night

£2,513 - £3,016 / week

92 Concord Lane

Osterville house

3 bedrooms / 2 bathrooms / sleeps 8

from £180 / night

£1,257 / week

77 Spice Lane

Osterville house

3 bedrooms / 3 bathrooms / sleeps 6

1

from £329 / night

£2,298 / week

FANTASTIC GET-A-WAY in OSTERVILLE W/BEACH PASS! 134586

Osterville house

3 bedrooms / 2 bathrooms / sleeps 8

from £123 / night

£862 / week

86 Leonard Road

Osterville house

4 bedrooms / 5 bathrooms / sleeps 8

from £770 / night

£5,385 / week

206 East Bay Road

Osterville house

5 bedrooms / 5 bathrooms / sleeps 8

1

from £1,538 / night

£10,770 / week

405 Sea View Avenue

Osterville house

10 bedrooms / 12 bathrooms / sleeps 22

3

from £1,949 / night

£13,642 - £17,950 / week

94 Waterfield Road

Osterville house

4 bedrooms / 2 bathrooms / sleeps 8

2

from £195 / night

£1,365 / week

12 Cockachoiset Lane

Osterville house

3 bedrooms / 3 bathrooms / sleeps 8

from £513 / night

£3,590 / week

17 Indian Trail

Osterville house

9 bedrooms / 9 bathrooms / sleeps 1

1

from £3,077 / night

£21,540 / week

44 Wianno Circle

Osterville house

4 bedrooms / 2 bathrooms / sleeps 8

from £513 / night

£3,590 / week

31 Parker Road

Osterville house

4 bedrooms / 4 bathrooms / sleeps 10

from £513 / night

£3,590 - £5,385 / week

344 Bridge Street

Osterville house

4 bedrooms / 5 bathrooms / sleeps 9

1

from £769 / night

£5,385 / week

Waterfront Home in Oyster Harbors - beach + dock

Osterville house

4 bedrooms / 3 bathrooms / sleeps 8

from £935 / night

£6,544 / week

271 Westwind Cir

Osterville house

3 bedrooms / 4 bathrooms / sleeps 6

2

from £101 / night

£718 - £1,293 / week

340 Grand Island Drive

Osterville house

6 bedrooms / 6 bathrooms / sleeps 12

from £1,538 / night

£10,770 / week

Newly Renovated Osterville Home. Minutes from Beach, Lake, and Center of Town.

Osterville house

3 bedrooms / 2 bathrooms / sleeps 8

from £283 / night

£1,975 / week

154 Scudder Road

Osterville house

4 bedrooms / 4 bathrooms / sleeps 8

1

from £564 / night

£3,949 - £4,452 / week

532 Wianno Avenue

Osterville house

5 bedrooms / 4 bathrooms / sleeps 10

1

from £667 / night

£4,667 - £6,103 / week

OSTERVILLE CHARMER IN THE VILLAGE! 142484

Osterville house

3 bedrooms / 3 bathrooms / sleeps 6

from £216 / night

£1,508 / week

Ideal Osterville Family Vacation Home w/AC, KIng Beds and Ocean/ Pond Beach Pass

Osterville house

4 bedrooms / 2 bathrooms / sleeps 8

from £372 / night

£2,601 / week

Osterville Home - 2.5 Mi. to Craigville Beach

Osterville house

4 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 45 minutes

from £175 / night

£1,220 / week

394 Old Mill Road

Osterville house

3 bedrooms / 2 bathrooms / sleeps 6

from £185 / night

£1,293 - £1,580 / week

236 Smoke Valley Road, #B

Osterville house

3 bedrooms / 3 bathrooms / sleeps 5

from £257 / night

£1,795 - £3,590 / week

154 Hollingsworth

Osterville house

4 bedrooms / 4 bathrooms / sleeps 7

from £513 / night

£3,590 / week

22 Sea View Avenue

Osterville house

4 bedrooms / 5 bathrooms / sleeps 10

from £1,538 / night

£10,770 - £12,206 / week

166 North Bay Road

Osterville house

7 bedrooms / 10 bathrooms / sleeps 10

from £1,795 / night

£12,565 / week

30 Oakdale Path

Osterville house

5 bedrooms / 7 bathrooms / sleeps 10

from £1,897 / night

£13,283 / week

235 Bridge Street

Osterville house

4 bedrooms / 4 bathrooms / sleeps 8

from £564 / night

£3,949 / week

Great rentals within 20 miles that match your search

Chappy Wind Farm

Edgartown house

3 bedrooms / 3 bathrooms / sleeps 8

from £281 / night

£1,965 / week

Historic Landmark Colonial in Heart of Edgartown

Edgartown house

4 bedrooms / 3 bathrooms / sleeps 8

from £940 / night

£6,577 / week

Ocean Front - Beautiful ocean views from all rooms

New Seabury condo

2 bedrooms / 3 bathrooms / sleeps 6

Responds fast! avg. 1 hour 1 minutes

from £336 / night

£2,349 / week

Jewel by the Sea

West Yarmouth house

6 bedrooms / 3 bathrooms / sleeps 12

2

from £470 / night

£3,289 / week

Private Twin Room in Cozy Cottage

Oak Bluffs house

1 bedroom / 1 bathroom / sleeps 2

from £283 / night

£1,977 / week

Viewing 40 of 1,781
rentals in Osterville