45 Best Vacation Rentals in Osterville - Holiday Lettings - Cabins

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2,256 Vacation rentals

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

24

Osterville Vacation home rental

Cape Cod / Osterville

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets
Sit by the heated pool and relax after a day at Dowses beach or take a stroll to Osterville village. This classic Cape Cod home is situated in the heart of Wianno on a secluded and lushly landscaped approx. acre of land. Great deck for entertaining stretching along the …see more

from $1,072 / night

$7,500 / week

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from $1,072 / night

46

Vacation home in Osterville

Cape Cod / Osterville

9 1 1 night min

  • 9 bedrooms
  • Sleeps 1
  • 1 night min
  • Ask about children
  • Ask about pets
Quiet luxury on the waters edge. Feel at one with the sand, surf, and sun while luxuriating on your own beach area surrounded by private and lush 26 acres in this exclusive gated paradise that is Oyster Harbors. Complete with a tennis court, beach house, dock and beach …see more

from $3,571 / night

$25,000 / week

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from $3,571 / 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

43

Vacation home with swimming pool in Osterville

Cape Cod / Osterville

6 10 1 night min

  • 6 bedrooms
  • Sleeps 10
  • 1 night min
  • Swimming pool
  • Ask about children
  • Ask about pets
Robert Paul Properties Luxury collection rental home. The very best of old + new! 4500+ square feet of vintage Cape charm conscientiously updated for today’s lifestyles. 1930’s summer home on Nantucket Sound. Private beach with ocean views from every room. Modern amenit …see more

from $2,571 / night

$18,000 - $20,000 / week

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from $2,571 / 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

14

Vacation home in Osterville

Cape Cod / Osterville

2 4 1 night min

  • 2 bedrooms
  • Sleeps 4
  • 1 night min
  • Ask about children
  • Ask about pets
This is the most charming and updated cottage in the "village" that you will find! Just 1 block to all Osterville shops and restaurants. This stunning two bedroom gem is totally turn key with custom and designer details throughout. The pictures say it all! central air, …see more

from $228 / night

$1,600 / week

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from $228 / night

21

Vacation home in Osterville

Cape Cod / Osterville

8 20 1 night min

  • 8 bedrooms
  • Sleeps 20
  • 1 night min
  • Ask about children
  • Pet friendly
Cape Cod charm in every space of this home. This Osterville private compound has lots of living areas and expansive water views from both main home and boathouse. This Estate offers a beach, tennis court, hot tub and deep-water dock. Close to Osterville village and all …see more

from $1,214 / night

$8,500 - $17,000 / week

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from $1,214 / night

27

Osterville Vacation home rental

Cape Cod / Osterville

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
  • 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

24

Vacation home in Osterville

Cape Cod / Osterville

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Ask about children
  • Ask about pets
Charming three bedroom home in Osterville with an open floor plan. First floor master with an en-suite bath, spacious dining room, three-season glassed sun room overlooking a fully fenced yard. The two additional large bedrooms share the upstairs bathroom. This home als …see more

from $428 / night

$3,000 / week

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from $428 / night

27

Osterville Vacation home rental

Cape Cod / Osterville

4 9 1 night min

  • 4 bedrooms
  • Sleeps 9
  • 1 night min
  • Ask about children
  • Ask about pets
Exclusive Robert Paul Properties rental home in the sought after Wianno Circle neighborhood. New to rental market this home offers four bedrooms, two full bath and large spaces. Kitchen is newly renovated for 2018. There is a den with TV, living room, eat in kitchen tha …see more

from $428 / night

$3,000 / week

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from $428 / night

22

Osterville Vacation home rental

Cape Cod / Osterville

3 8 1 night min

  • 3 bedrooms
  • Sleeps 8
  • 1 night min
  • Ask about children
  • Pet friendly
Its always nice to be a short stroll to the village and not far from the beach. This Osterville rental home has these qualities and more. Large open concept kitchen and eating area with TV, formal living room and den with additional flat screen TV, couch and bunk bed …see more

from $414 / night

$2,900 / week

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from $414 / night

(1) Excellent 

19

Vacation home in Osterville

Cape Cod / Osterville

4 8 1 night min

  • 4 bedrooms
  • Sleeps 8
  • 1 night min
  • Ask about children
  • Pet friendly
Close to Osterville village and Joshua's Pond, this charming rental home has four bedrooms including a master suite with full bath on second level and three bedrooms and a full bath on first floor. Living room, family room and eat-in kitchen. There is a spacious deck of …see more

from $271 / night

$1,900 / week

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from $271 / night

37

Vacation home with swimming pool in Osterville

Cape Cod / Osterville

5 10 1 night min

  • 5 bedrooms
  • Sleeps 10
  • 1 night min
  • Swimming pool
  • Ask about children
  • Ask about pets
Robert Paul Properties Luxury collection rental home. Unique opportunity to enjoy panoramic views of Cotuit and North Bay from this stunning home located in prestigious Oyster Harbors on the aptly named Sand Point. With an eye towards preserving the Cape Cod charm of t …see more

from $2,000 / night

$14,000 - $20,000 / week

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from $2,000 / night

24

Vacation home in Osterville

Cape Cod / Osterville

3 8 1 night min

  • 3 bedrooms
  • Sleeps 8
  • 1 night min
  • Ask about children
  • Pet friendly
You get home from one of the beaches the complimentary beach pass allows you to visit, then washing off the sand in your enclosed outdoor shower. Relax on the sun splashed outdoor deck with your guests while enjoying a cold refreshing beverage and a delicious meal prepa …see more

from $214 / night

$1,500 - $2,250 / week

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from $214 / night

(1) Excellent 

28

Home rental in Osterville

Cape Cod / Osterville

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
  • 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

13

Home rental in Osterville

Cape Cod / Osterville

3 6 1 night min

  • 3 bedrooms
  • Sleeps 6
  • 1 night min
  • Ask about children
  • Ask about pets
In desirable Wianno Circle location of Osterville. Close to Dowses Beach and village. Great location for this three bedroom, two full bath home. Deck, large yard with gas grill and patio set. New for 2017: central air. Beach pass is provided. …see more

from $385 / night

$2,700 / week

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from $385 / 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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from $643 / night

(2) Very Good 

49

Osterville Vacation home rental

Cape Cod / Osterville

11 20 1 night min

  • 11 bedrooms
  • Sleeps 20
  • 1 night min
  • Ask about children
  • Ask about pets
Welcome to Lands End where wonderful old world charm meets the beach out the back door. This 11 bedroom home with a private beach is perfect for a large gathering. Offering a tennis court and basketball hoop, a beach house on the sand with an enclosed outdoor shower, …see more

from $1,357 / night

$9,500 - $12,500 / week

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from $1,357 / night

26

Vacation home in Osterville

Cape Cod / Osterville

5 12 1 night min

  • 5 bedrooms
  • Sleeps 12
  • 1 night min
  • Ask about children
  • Ask about pets
Less than a mile to the heart of Osterville and one mile to Dowses Beach, this location is perfect! This lovely, light and bright home is filled with Cape Cod style! Large open kitchen and dining area as well as a comfortable den with TV. Three bedrooms on the first f …see more

from $357 / night

$2,500 - $5,000 / week

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from $357 / night

(1) Excellent 

22

Vacation home in Osterville

Cape Cod / Osterville

4 10 1 night min

  • 4 bedrooms
  • Sleeps 10
  • 1 night min
  • Ask about children
  • Ask about pets
Enjoy sunsets from this charming Cape Cod rental overlooking West Bay. A deeded path meanders down to the Bay for easy access to the water. This four bedroom, 3.5 bath home is perfectly located in the heart of Wianno and within walking distance to Osterville village wit …see more

from $571 / night

$4,000 / week

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from $571 / night

35

Vacation home in Osterville

Cape Cod / Osterville

12 15 1 night min

  • 12 bedrooms
  • Sleeps 15
  • 1 night min
  • Ask about children
  • Ask about pets
Cape Cod charm at its best and most elegant. Exquisite Ocean front home with private beach making for an ideal vacation. There are 12 bedrooms and large open areas for gathering. Kitchen, pantry, dining room and sitting room overlooking the water with pool table. Th …see more

from $1,285 / night

$9,000 - $12,500 / week

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from $1,285 / night

29

Vacation home with swimming pool in Osterville

Cape Cod / Osterville

7 14 1 night min

  • 7 bedrooms
  • Sleeps 14
  • 1 night min
  • Swimming pool
  • Ask about children
  • Ask about pets
Robert Paul Properties Luxury collection rental home. Enter the private drive towards your Cape Cod rental home. This stunning seven-bedroom home has a lot to offer for your summer vacation. Walk into the foyer to large open floor plan including, eat in Gourmet kitche …see more

from $857 / night

$6,000 - $12,000 / week

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from $857 / night

(1) Excellent 

28

Home rental in Osterville with swimming pool

Cape Cod / Osterville

6 12 1 night min

  • 6 bedrooms
  • Sleeps 12
  • 1 night min
  • Swimming pool
  • Ask about children
  • Pet friendly
Robert Paul Properties Luxury collection rental home. Welcome to Osterville! This spacious newly renovated rental property is located in the gated community of Oyster Harbors with a heated pool, water view of West Bay and private dock. Drink your coffee on the terrace o …see more

from $3,571 / night

$25,000 / week

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from $3,571 / night

16

Home rental in Osterville

Cape Cod / Osterville

6 10 1 night min

  • 6 bedrooms
  • Sleeps 10
  • 1 night min
  • Ask about children
  • Pet friendly
Great home located between Dowses Beach and Osterville village. There are six bedrooms and four full baths and central air for your comfort. The first level offers a large formal dining room, well-equipped kitchen with a casual eating area, comfortable living room, two …see more

from $428 / night

$3,000 - $4,500 / week

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from $428 / 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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avg. 42 minutes

from $3,572 / night

(1) Excellent 

18

Vacation home with swimming pool in Osterville

Cape Cod / Osterville

5 12 1 night min

  • 5 bedrooms
  • Sleeps 12
  • 1 night min
  • Swimming pool
  • Ask about children
  • Ask about pets
Robert Paul Properties Luxury collection rental home. This beautiful five bedroom home is nestled on a private three acre lot in the desirable area of Seapuit, close to Osterville village center. The exterior is highlighted by lush landscaping and a stunning heated swi …see more

from $1,214 / night

$8,500 - $11,500 / week

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from $1,214 / night

23

Vacation home with swimming pool in Osterville

Cape Cod / Osterville

4 10 1 night min

  • 4 bedrooms
  • Sleeps 10
  • 1 night min
  • Swimming pool
  • Ask about children
  • Ask about pets
Charming Cape Cod home in the heart of the village! Lovely brand new to rental market home with resort heated pool and stunning area in back yard. Home has first floor bedroom, living room, powder room, kitchen, and dining room, The 2nd floor features two charmin …see more

from $500 / night

$3,500 - $7,000 / week

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from $500 / night

(1) Excellent 

27

Osterville Vacation home accommodation

Cape Cod / Osterville

5 8 1 night min

  • 5 bedrooms
  • Sleeps 8
  • 1 night min
  • Ask about children
  • Ask about pets
Cape Cod waterfront home in Osterville. Magnificent sun-filled summer home with a private deep water dock on East Bay and a short walk from both beautiful Dowses Beach and from Osterville village for easy access to fine dining and quaint shops. A private retreat that of …see more

from $1,214 / night

$8,500 - $11,000 / week

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from $1,214 / night

19

Vacation home in Osterville

Cape Cod / Osterville

4 8 1 night min

  • 4 bedrooms
  • Sleeps 8
  • 1 night min
  • Ask about children
  • Ask about pets
Bright, lovely secluded home on almost three acres in prestigious Seapuit enclave of large estate homes. Main house has three bedrooms (each with private bath). Meticulously maintained with beautiful landscaping, serenity, and privacy. Royal Barry Wills inspired home is …see more

from $500 / night

$3,500 - $4,500 / week

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from $500 / night

34

Osterville Vacation home rental

Cape Cod / Osterville

3 1 1 night min

  • 3 bedrooms
  • Sleeps 1
  • 1 night min
  • Ask about children
  • Ask about pets
Exclusive Robert Paul Properties rental home. This Osterville rental home has it all. Close to Dowses beach, close to village and Sand Pond is in the back of the home and Joshua's Pond is across the street. The first floor has a great open floor plan with living room, d …see more

from $557 / night

$3,900 / week

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from $557 / night

(1) Excellent 

64

Osterville Vacation home rental

Cape Cod / Osterville

10 22 1 night min

  • 10 bedrooms
  • Sleeps 22
  • 1 night min
  • Ask about children
  • Ask about pets
Robert Paul Properties Luxury collection rental home. Located in desirable Osterville Village and just a few yards from the warm waters of Nantucket sound is your own private beach. This 4 acre luxury rental home also has a heated pool and hot tub. There is a main home …see more

from $1,714 / night

$12,000 - $23,500 / week

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from $1,714 / 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

28

Vacation home in Osterville

Cape Cod / Osterville

5 10 1 night min

  • 5 bedrooms
  • Sleeps 10
  • 1 night min
  • Ask about children
  • Ask about pets
This wonderful Osterville lodge overlooking Neck Pond is a great private get-away. Located across from the Wianno Golf Club, this is an ideal location. Less than a mile from the village and a mile to Dowses Beach. The house, set on a private acre, has a lovely porch, fi …see more

from $642 / night

$4,500 / week

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from $642 / night

32

Vacation home in Osterville

Cape Cod / Osterville

4 8 1 night min

  • 4 bedrooms
  • Sleeps 8
  • 1 night min
  • Ask about children
  • Ask about pets
Best of both worlds, close to Dowses Beach and walk to Osterville village. First floor has large open space with eat-in kitchen, dining area, fire placed living room, half bath, laundry and master bedroom with king bed ensuite. Walk up to the second floor for three m …see more

from $357 / night

$2,500 - $5,000 / week

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from $357 / night

12

Vacation home in Osterville

Cape Cod / Osterville

3 5 1 night min

  • 3 bedrooms
  • Sleeps 5
  • 1 night min
  • Ask about children
  • Ask about pets
This rental is as cute as a button. Located between Dowses Beach and the village. A truly hidden gem! There are three bedrooms and one full bath. The first level has a queen bedroom, dining/living area, kitchen and full bath. There are two bedrooms upstairs. One with a …see more

from $357 / night

$2,500 / week

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from $357 / night

18

Vacation home in Osterville

Cape Cod / Osterville

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
  • 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 and a beautifully appointed new kitchen that includes a large breakfast bar,dining area …see more

from $186 / night

$1,300 / week

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from $186 / night

15

Osterville Vacation home rental

Cape Cod / Osterville

3 5 1 night min

  • 3 bedrooms
  • Sleeps 5
  • 1 night min
  • Ask about children
  • Ask about pets
Spectacular three bedroom Nantucket style cottage, fronting for 500' on the waters of Warrens Cove. This pristine, year-around home has been newly renovated with meticulous detail. The property has two decks, expansive waterviews, overlooking a 40 foot fishing pier adeq …see more

from $428 / night

$3,000 - $4,100 / week

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from $428 / night

25

Vacation home in Osterville

Cape Cod / Osterville

3 8 1 night min

  • 3 bedrooms
  • Sleeps 8
  • 1 night min
  • Ask about children
  • Pet friendly
Wonderful Osterville location just steps to the Marina is known as the "Windmill House." This stunning 3 bedroom, 3 bath home is nicely appointed with a soaring two story living room with fireplace, flat screen TV, and French doors to a private patio. There is a 1st flo …see more

from $614 / night

$4,300 / week

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from $614 / night

(3) Excellent 

31

Home rental in Osterville

Cape Cod / Osterville

4 8 1 night min

  • 4 bedrooms
  • Sleeps 8
  • 1 night min
  • Ask about children
  • Pet friendly
Lovely four bedroom, two bath rental home in the heart of Osterville. Short stroll to village and not far from Dowses Beach with a beach pass provided. Two bedrooms, living room, dining room and sitting area on the first level as well as a full bath. Second level has t …see more

from $271 / night

$1,900 - $2,800 / week

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from $271 / night