10 Best Vacation Rentals in Osterville - Holiday Lettings - Cabins

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2,393 Vacation rentals

27

Osterville Vacation home rental

Cape Cod / Osterville

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Air conditioning
BEAUTIFUL SEAPUIT HOME IN OSTERVILLE NEAR VILLAGE EXQUISITE home on almost three acres in Osterville s coveted "Seapuit" enclave (which fronts North Bay) ~ A gracious & comfortable gem with 3 bedrooms (sleeps six plus a love seat/sofa bed in the Den) 3 .5 baths~each bed …see more

from $415 / night

$2,900 / week

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from $415 / night

20

Vacation home in Osterville

Cape Cod / Osterville

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Private garden
Desired location on Cape Cod! It's always nice to be a short stroll to the village with it's shops and great restaurants and not far from the beach. This Osterville rental home has these qualities and more. Walk into a large Living room with TV, eat in Kitchen with …see more

from $300 / night

$2,100 / week

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from $300 / night

12

Vacation home in Osterville

Cape Cod / Osterville

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Child friendly
  • Air conditioning
  • Pet friendly
Welcome to what we affectionately refer to as "The Black Pearl," a vintage home located in one of the Cape's most coveted locations. Oyster Harbors is a private island only accessible to residents, club members & guests! A deep water dock with access to fast water in m …see more

from $3,572 / night

$25,000 / week

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Responds fast!
avg. 42 minutes

from $3,572 / night

(1) Excellent 

28

Home rental in Osterville

Cape Cod / Osterville

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Child friendly
  • Air conditioning
SOUTH of RTE. 28 ~ OSTERVILLE !! BEACH PASS! Come enjoy this NEWLY REMODELED bright & sunny vacation home on a quiet street in lovely Osterville Woods! Quick access to beautiful Dowses Beach on Nantucket Sound (BEACH PASS PROVIDED ) Joshua s "cystal clear" Pond & the ch …see more

from $222 / night

$1,550 - $1,700 / week

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from $222 / night

24

Vacation home in Osterville

Cape Cod / Osterville

3 9 Min stay varies

  • 3 bedrooms
  • Sleeps 9
  • Min stay varies
  • Child friendly
  • Air conditioning
  • Private garden
Picturesque, completely renovated 8 room seaside home is surrounded by stunning blue hydrangeas & roses. Just 1.5 blocks to Osterville center & walk/bike to harbor and beach; Light and airy with a nautical theme and open floor plan. Gourmet kitchen. The space This new …see more

from $400 / night

$2,800 / week

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from $400 / night

4

Vacation home in Osterville

Cape Cod / Osterville

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Child friendly
  • Air conditioning
Oyster Harbors Classic Cape Retreat & Guest Cottage- Located on Oyster Harbors, a private island in a gated community with 24 hour security, one of Osterville's premier neighborhoods. This 1926 home features a newly renovated kitchen ( 2016) with all new appliances. Als …see more

from $643 / night

$4,500 / week

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Responds fast!
avg. 6 minutes

from $643 / night

23

Vacation home in Osterville

Cape Cod / Osterville

3 7 7 nights min

  • 3 bedrooms
  • Sleeps 7
  • 7 nights min
  • Nearest beach 0.32 mi
  • Child friendly
  • Air conditioning
Elf Hill Cottage is comprised of two double bedrooms, a third bedroom with two twin beds and a daybed for a child, two full bathrooms, a living room, dining room and sun room. There is an automatic garage. The house has been freshly painted, has hardwood floors upstai …see more

from $206 / night

$1,440 - $2,420 / week

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from $206 / night

29

Vacation home in Osterville

Cape Cod / Osterville

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly
  • Air conditioning
Quick drive to Beautiful Dowses BEACH! BEACH PASS PROVIDED! Newly remodeled lovely vacation home!! LOVELY NEWLY remodeled Open Concept three bedroom, 1.5 bath ranch with central A/C, Wi-Fi, and a beautifully appointed new kitchen that includes a large breakfast bar,din …see more

from $186 / night

$1,300 / week

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from $186 / night

28

Vacation home in Osterville

Cape Cod / Osterville

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly
Guests are sure to enjoy a memorable vacation in this family friendly 3 bedroom/2 bath residence. The property has Central Air Conditioning, washer/drier, and owners provide Beach Pass. The master bedroom has a king-sized bed, and the remaining bedrooms are furnished …see more

from $325 / night

$2,275 / week

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from $325 / night

32

Osterville Vacation home rental

Cape Cod / Osterville

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Child friendly
This stunning waterfront home sits on a small bluff overlooking Cotuit Bay, Sampson's Island (Deadneck), and Martha's Vineyard on a clear day. Easy access to its own private beach and a deep water dock can accommodate boat 40+ feet with electrical hook-up. There are kay …see more

from $995 / night

$6,965 / week

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from $995 / night