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Osterville Rentals

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1,547 Houses

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

Osterville house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$171

271 Westwind Cir

Osterville house

3 bedrooms / 4 bathrooms / sleeps 6

Price per night from

$141

Waterfront Home in Oyster Harbors - beach + dock

Osterville house

4 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$1,144

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

Osterville house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$375

Osterville Home - 2 1/2 Miles to Craigville Beach!

Osterville house

4 bedrooms / 2 bathrooms / sleeps 8

Responds fast! avg. 14 minutes

Price per night from

$243

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

Osterville house

4 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$486

OSTERVILLE CHARMER IN THE VILLAGE! 142484

Osterville house

3 bedrooms / 3 bathrooms / sleeps 6

Price per night from

$300

Beautifully Updated Home | Backyard Oasis, New Pool & Firepit | Near Beach

Osterville house

4 bedrooms / 4 bathrooms / sleeps 12

Price per night from

$505

Great rentals within 20 miles that match your search

Chappy Wind Farm

Edgartown house

3 bedrooms / 3 bathrooms / sleeps 8

Price per night from

$388

Jewel by the Sea

West Yarmouth house

6 bedrooms / 3 bathrooms / sleeps 12

Price per night from

$648

Private Twin Room in Cozy Cottage

Oak Bluffs house

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$390

Guest Room in a Cozy Cottage

Oak Bluffs private room

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$390

Private Carriage House Loft. Waterfront. Dog friendly. Private.

Wareham barn

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$195

X-Large Cape Cod Beach House

Falmouth house

7 bedrooms / 4 bathrooms / sleeps 16

Responds fast! avg. 42 minutes

Price per night from

$835

Oak Bluffs Home walk to town

Oak Bluffs house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$464

Cape Cod Beach House Dogs are ok but we need to discuss before booking.

Wareham house

5 bedrooms / 4 bathrooms / sleeps 10

Price per night from

$1,113

Charming 3 Bedroom Colonial In Popponesset

Mashpee house

3 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$956

Unique & Private 3 Bedroom Brewster Home

Brewster house

3 bedrooms / 2 bathrooms / sleeps 8

Price per night from

$372

Charming Cape Cod Cottage/ Walk to Beach/Canal

Sandwich house

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$61

Yarmouth on Cape Code on Labor Day weekend

West Yarmouth condo

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$222

Bayside Beach house in Maravista, walk to beach

Teaticket house

2 bedrooms / 1 bathroom / sleeps 5

Price per night from

$255

Price per night from

$316

Fabulous Cape Cod House With Great Water Views

West Yarmouth house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$650

Sunset Charter on Private Trawler Yacht 42'-

Hyannis yacht

2 bedrooms / 2 bathrooms / sleeps 4

Price per night from

$779

MY POPPY HEAVEN

New Seabury house

3 bedrooms / 3 bathrooms / sleeps 10

Price per night from

$909

2 BR Cape Cod Vacation Rental

Mashpee house

2 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$1,856

Luxurious & Spacious Waterfront Home on Swimmable Private Beach. Pet OK.

Barnstable house

3 bedrooms / 4 bathrooms / sleeps 8

Price per night from

$1,484

High-end Brewster ,Mass. Bay view town home

Brewster apartment

2 bedrooms / 2 bathrooms / sleeps 5

Price per night from

$464

Cape Cod timeshare condo rental, Mashpee Ma. (SeaMist)

Mashpee condo

1 bedroom / 2 bathrooms / sleeps 4

Price per night from

$233

Charming Cape Home/Walk to Beach

Falmouth house

3 bedrooms / 2 bathrooms / sleeps 9

Price per night from

$547

Price per night from

$186

Cape Cod Charm in Falmouth Village

Falmouth studio

Studio / 1 bathroom / sleeps 4

Price per night from

$422

Private Katama neighborhood with association beach

Edgartown house

3 bedrooms / 2 bathrooms / sleeps 6

Price per night from

$974

Cotuit Cottage overlooking the harbor

Cotuit house

2 bedrooms / 1 bathroom / sleeps 4

Price per night from

$416

Luxury Home - Steps to Sandy Beach

South Yarmouth house

4 bedrooms / 3 bathrooms / sleeps 7

“Lifestyles of the Rich and Famous” Every inch of this beautiful house is impressive beyond words. The kitchen is spectacular. Unbelievable views, and fenced in yard. Great for kids playing. Walk across street to beach. Easy location. This house was "higher end" than our usual summer vacation - and I felt like I was staying in a mansion. Don't miss out on your morning coffee on the deck! The children and teens really loved this spot as well.

Price per night from

$1,789

1st Floor Oceanfront Condo with Private Beach & Panoramic Views

Hyannis condo

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$443

The Outback E Dennis/Brewster 1 bedroom 2 Guests Only 2019 availability

East Dennis cottage

1 bedroom / 1 bathroom / sleeps 2

Price per night from

$222

$225/Night Bargain deal at Cape Cod Resort. BARGAIN DEAL

Dennis Port condo

1 bedroom / 1 bathroom / sleeps 4

Price per night from

$285

Viewing 38 of 1,547
rentals in Osterville

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