50 Best Vacation Rentals in Osterville - Holiday Lettings - Cabins

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55 Vacation rentals

22

Osterville Vacation home rental

Cape Cod / Osterville

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
  • Ask about pets
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 beds f …see more

from $415 / night

$2900 / week

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from $415 / night

13

Home rental in Osterville

Cape Cod / Osterville

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights 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. Additional amenities inclu …see more

from $379 / night

$2651 / week

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from $379 / night

26

Vacation home with swimming pool in Osterville

Cape Cod / Osterville

6 10 7 nights min

  • 6 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets
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 amenities include heated pool, full A/C, updated eat-in kitc …see more

from $2572 / night

$18000 - $20000 / week

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from $2572 / night

26

Vacation home in Osterville

Cape Cod / Osterville

5 12 7 nights min

  • 5 bedrooms
  • Sleeps 12
  • 7 nights min
  • Ask about children
  • Ask about pets
Less than a mile to heart of downtown Osterville and 1.5 miles to Dowses Beach, this location is perfect! This lovely, light and bright home is filled with Cape Cod style! Large open kitchen and dining room as well as a den with two bedrooms on the first floor and a ful …see more

from $715 / night

$5000 / week

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from $715 / night

21

Vacation home in Osterville

Cape Cod / Osterville

8 20 7 nights min

  • 8 bedrooms
  • Sleeps 20
  • 7 nights min
  • Ask about children
  • Ask about pets
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 $2358 / night

$16500 / week

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from $2358 / night

21

Vacation home in Osterville

Cape Cod / Osterville

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Ask about children
  • Ask about pets
Located in the prestigious gated community of Oyster Harbors. This Cape Cod rental home features a newly renovated kitchen with all new appliances, first floor master suite, two staircases leading to four more bedrooms and two full baths. There is a one bedroom apartmen …see more

from $715 / night

$5000 / week

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from $715 / night

53

Home accommodation in Osterville

Cape Cod / Osterville

6 13 7 nights min

  • 6 bedrooms
  • Sleeps 13
  • 7 nights min
  • Ask about children
  • Ask about pets
This wonderful Osterville home overlooking Neck Pond is a great private getaway. Located across from the Wianno Golf Club, this is an ideal location. Not far from the village and Dowses Beach. The house, set on a private acre, has a lovely porch, six bedrooms and four b …see more

from $643 / night

$4500 / week

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from $643 / night

21

Vacation home in Osterville

Cape Cod / Osterville

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
  • Ask about pets
Do you have allergies? If so, then this Osterville rental home is the perfect home for you. This house is completely scent free. Walk to Main Street to Osterville village and it is only 1.5 miles from Dowses Beach. This home has a well-appointed kitchen that opens to a …see more

from $715 / night

$5000 / week

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from $715 / night

24

Vacation home in Osterville

Cape Cod / Osterville

3 8 7 nights min

  • 3 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
  • Ask about pets
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 $143 / night

$1000 - $2250 / week

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from $143 / night

24

Vacation home in Osterville

Cape Cod / Osterville

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights 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 $400 / night

$2800 / week

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from $400 / 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 $200 / night

$1400 - $2360 / week

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from $200 / 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 $300 / night

$2100 / week

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from $300 / night

16

Home rental in Osterville

Cape Cod / Osterville

6 10 7 nights min

  • 6 bedrooms
  • Sleeps 10
  • 7 nights min
  • Ask about children
  • Ask about pets
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 $643 / night

$4500 / week

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from $643 / night

52

Osterville Vacation home rental

Cape Cod / Osterville

10 20 7 nights min

  • 10 bedrooms
  • Sleeps 20
  • 7 nights min
  • Ask about children
  • Ask about pets
Beachfront Estate custom built in 2005 with path to a private beach. This home has glorious ocean views from most all of the rooms and there is a dune path to your own private beach on Nantucket Sound just past the cottage. New for 2017: heated pool! The main home has s …see more

from $2786 / night

$19500 / week

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from $2786 / 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

$1550 - $1700 / week

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from $222 / night

26

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 $1072 / night

$7500 / week

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from $1072 / night

12

Vacation home accommodation

Cape Cod / Osterville

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights min
  • Ask about children
  • Ask about pets
Wonderful location! Close to Dowses Beach and not far from Main Street, also close to Wianno Golf Course and Crystal Lake! This lovely two bedroom, one bath home sits on a quiet village lane. Enjoy casual elegance and an open floor plan with wood floors, living room and …see more

from $415 / night

$2900 / week

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from $415 / night

25

Home rental in Osterville

Cape Cod / Osterville

2 6 7 nights min

  • 2 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
  • Ask about pets
This brand new home is stunning! Just built with luxury touches and all on one level. Large open floor plan with comfortable living room that opens to the gourmet kitchen, dining area and half bath. King master with en-suite bath with soaking tub and steam shower. Secon …see more

from $572 / night

$4000 / week

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from $572 / night

14

Vacation home in Osterville

Cape Cod / Osterville

2 4 7 nights min

  • 2 bedrooms
  • Sleeps 4
  • 7 nights 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 little two bedroom gem is totally turn key with custom and designer details throughout. The pictures say it all! centra …see more

from $229 / night

$1600 / week

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from $229 / night

41

Vacation home in Osterville

Cape Cod / Osterville

9 15 7 nights min

  • 9 bedrooms
  • Sleeps 15
  • 7 nights 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 $3572 / night

$25000 / week

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from $3572 / night

26

Home accommodation in Osterville

Cape Cod / Osterville

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Ask about children
  • Ask about pets
Where else can you stroll to the Osterville village, North Bay and Wianno Golf Course? There are six bedrooms and three full and one half baths. Lush landscaping to the mahogany deck with gazebo overlooking this private backyard to the well thought out kitchen with ever …see more

from $858 / night

$6000 / week

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from $858 / night

35

Home rental in Osterville

Cape Cod / Osterville

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
  • Ask about pets
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 tw …see more

from $400 / night

$2800 / week

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from $400 / night

19

Osterville Vacation home rental

Cape Cod / Osterville

5 8 7 nights min

  • 5 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
  • Ask about pets
Private gated community rental home surrounded by water in prestigious Oyster Harbors. This Shingle Cottage style home was built in 2004 and comes with a sandy beach area as well as amazing attention to details. Over 3100 square feet with grand entry and open floor plan …see more

from $1215 / night

$8500 - $12000 / week

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from $1215 / night

28

Osterville Vacation home accommodation

Cape Cod / Osterville

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights 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 $1215 / night

$8500 / week

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from $1215 / night

37

Vacation home with swimming pool in Osterville

Cape Cod / Osterville

5 10 7 nights min

  • 5 bedrooms
  • Sleeps 10
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets
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 the property, owner and builder created a home that offe …see more

from $2858 / night

$20000 / week

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from $2858 / night

12

Vacation home in Osterville

Cape Cod / Osterville

3 5 7 nights min

  • 3 bedrooms
  • Sleeps 5
  • 7 nights 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 $358 / night

$2500 / week

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from $358 / night

15

Vacation home with swimming pool in Osterville

Cape Cod / Osterville

5 12 7 nights min

  • 5 bedrooms
  • Sleeps 12
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets
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 swimming pool and pool house with kitchenette and shower. …see more

from $1643 / night

$11500 / week

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from $1643 / night

25

Vacation home with swimming pool in Osterville

Cape Cod / Osterville

7 14 7 nights min

  • 7 bedrooms
  • Sleeps 14
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets
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 kitchen, with second additional kitchen nearby, formal dining …see more

from $1643 / night

$11500 / week

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from $1643 / night

28

Home rental in Osterville with swimming pool

Cape Cod / Osterville

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Ask about pets
Welcome to Osterville! Spacious newly renovated luxury rental property 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 or take a swim in the heated pool. Make plans to take your boat …see more

from $3572 / night

$25000 / week

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from $3572 / night

18

Vacation home in Osterville

Cape Cod / Osterville

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
  • Air conditioning
OSTERVILLE VILLLAGE NEAR SEAVIEW AVE. BEACH & DOWSES BEACH!! Seaview Avenue/ Wianno area of Osterville! Open concept Cape/ close to the small but beautiful Seaview Ave BEACH, Dowses Beach, or go to all of the many town of Barnstable public beaches, as Barnstable BEACH …see more

from $243 / night

$1700 - $1900 / week

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from $243 / night

35

Vacation home in Osterville

Cape Cod / Osterville

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
  • Ask about pets
This home has been totally renovated from top to bottom for the rental season. There are four bedrooms, a master suite on the first level and three bedrooms upstairs. Three full baths and TV room in lower level. Sun porch with flat screen and office area. Great outside …see more

from $758 / night

$5301 / week

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from $758 / 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 $272 / night

$1900 - $4500 / week

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from $272 / night

(1) Excellent 

22

Osterville Vacation home rental

Cape Cod / Osterville

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Beach/lakeside relaxation
  • Nearest beach 2 mi
  • Child friendly
Bright & lovely, recently decorated/furnished home on almost 3 acres in Osterville's coveted SEAPUIT enclave on North Bay. Main House has Central A/C and 3 ensuite bedrooms. The 4th BR is in the STUDIO COTTAGE, available as an OPTION for additional $700 per week (summer …see more

from $415 / night

$2900 - $3901 / week

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from $415 / night

(1) Very Good 

48

Osterville Vacation home rental

Cape Cod / Osterville

11 20 7 nights min

  • 11 bedrooms
  • Sleeps 20
  • 7 nights min
  • Ask about children
  • Ask about pets
Wonderful old world charm! 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, a deck for watching the magnificent Cape Cod sunsets or simply …see more

from $1786 / night

$12500 / week

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from $1786 / night

19

Osterville Vacation home rental

Cape Cod / Osterville

3 6 7 nights min

  • 3 bedrooms
  • Sleeps 6
  • 7 nights min
  • Ask about children
  • Ask about pets
This quaint affordable old world charm Osterville rental home is not far from the village and close to Dowses Beach. There are three bedrooms: 1. king bed 2. king bed and 3. queen bed. Two full baths and one half bath. Relax on the back deck with gas grill and nice priv …see more

from $258 / night

$1801 / week

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from $258 / night

(1) Excellent 

14

Vacation cottage in Osterville

Cape Cod / Osterville

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Lovely 2 Bedroom home on a quiet street in the desirable Wianno area of Osterville, Cape Cod or Osterville Village. (This is the section nearest to Dowses' Beach! You can't find a rental for this price this close to the beach in Osterville!!) The house is bright, c …see more

from $160 / night

$1050 - $1599 / week

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from $160 / night

29

Home rental in Osterville

Cape Cod / Osterville

3 10 7 nights min

  • 3 bedrooms
  • Sleeps 10
  • 7 nights min
  • Ask about children
  • Ask about pets
Imagine morning coffee on the second floor deck overlooking Crosby’s boat yard or relax on the front porch. Wonderful home close to village, Dowses Beach and all Osterville has to offer. There are three bedrooms [ and a bonus sleeping area bedroom ]and a guest cottage. …see more

from $929 / night

$6500 / week

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from $929 / night

21

Vacation home in Osterville

Cape Cod / Osterville

4 9 7 nights min

  • 4 bedrooms
  • Sleeps 9
  • 7 nights min
  • Ask about children
  • Ask about pets
New construction with 9 foot ceilings. This stunning Osterville rental home has spared no detail in comfort and luxury. Gourmet kitchen and seating area overlooks great back yard with seating on deck and fire pit. First floor en-suite master with queen bed, fireplace li …see more

from $986 / night

$6900 / week

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from $986 / night

22

Vacation home in Osterville

Cape Cod / Osterville

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights min
  • Ask about children
  • Ask about pets
Just a few steps to Osterville village center! Well-appointed and comfortable. New custom second floor master suite has been added. Spacious deck overlooking golf and Bay! This home backs up to the 6th hole of the Wianno Golf Course and is only a few houses away to Bay …see more

from $715 / night

$5000 / week

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from $715 / night

33

Vacation home in Osterville

Cape Cod / Osterville

4 8 7 nights min

  • 4 bedrooms
  • Sleeps 8
  • 7 nights 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, and master bedroom with king bed and full bath. Walk up to the second floor for three more b …see more

from $715 / night

$5000 / week

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from $715 / night

1