Osterville Rentals

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267 Houses

271 Westwind Cir

Osterville house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

Match: Garden

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Price per night from

$221

OSTERVILLE VILLAGE NEWLY RENOVATED ON 6 ACRES CLOSE TO BEACHES

Osterville house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Garden

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Price per night from

$1,032

Contemporary Gem with Private Pool!

Osterville house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Garden

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Price per night from

$402

Walk to Joshua Pond Beach & Downtown!

Osterville house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Match: Garden

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Price per night from

$224

Great rentals within 20 miles that match your search

Excellent location on Martha's Vineyard

Edgartown house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Garden

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Price per night from

$631

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

Barnstable house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Garden

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Price per night from

$1,311

Barnstable Village Private Pool

Barnstable house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 3

“Great place to stay” The home was clean and well maintained. The pool was a huge hit with my niece and the rest of the family. We were in a great location, close to a beach, some shops and restaurants.

Match: Garden

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Price per night from

$457

Beautiful vacation home for rent

Dennis house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Match: Garden

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Price per night from

$524

Waterfront, Quiet 3 BR Cape-Walk to Beach

Falmouth house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Garden

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Price per night from

$631

High End-suite style cottage 5 min bike ride to amazing Craigville Beach.

Centerville cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Match: Garden

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Price per night from

$344

Renovated Cape Cod Home -10 Minutes To Beaches & Ctr

Hyannis Port house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 7

Match: Garden

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Price per night from

$371

41 Cranberry Trail

East Sandwich house

  • 5 bedrooms
  • 4 bathrooms
  • sleeps 10

“most relaxing getaway ever.” My friends and I needed a break from the city this spring and this house served us incredibly well. It's spacious and, even with a house full of people, offers an incredible amount of privacy. The large kitchen is perfect for cooking group meals, and a back deck and side-yard tennis court make for ample opportunities to soak up the nature. Set on a private drive, the house is just a 5-minute walk to the beach, past beautiful cranberry bogs. Even though we were there in the early spring rather than prime beach-going weather, our time spent outdoors was time well spent--quiet, calm, and relaxing. We can't wait to go back.

Match: Garden

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Price per night from

$230

Heated Pool, AC, WiFi, Sleeps 18, 2 mi to beach!

Oak Bluffs house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 19

Match: Garden

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Price per night from

$6,880

Waterfront home - Spectacular Sunsets

Bourne house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 9

“Peace & Tranquility” I have stayed here 4+ times, and I come home relaxed and rejuvenated. It's centrally located in the middle of the western cape, the sunsets are perfect, we usually have meals out on the expansive deck, we bring our kayaks, watch the shipping entering the canal, walk/run/bike the canal path(both sides), cook or grill fresh seafood from local stores, enjoy the wine tastings at the Belfry, jump over to the vineyard for the day, and did I mention the sunsets? The home is roomy, light and airy, plenty of parking, just perfect for us.

Match: Garden

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Price per night from

$631

“Great time!!” This wonderful home was great for our Cape vacation! The home is beautiful and the owner's pride and love for their home shows throughout the property. The owners were excellent to work with, very professional and very responsive to inquiries. The house is beautifully decorated and extremely well stocked with everything we needed to make our vacation perfect. We appreciated all the amenities - inside and out, the huge rear deck was one of our favorite places to relax and enjoy the quiet area and the beautiful landscaping, we could even hear the waves at night. The location was very convenient to restaurants, shops and beaches and is centrally located to exploring anywhere on the Cape. We are looking forward to calling this our "home away from home" again!!!

Match: Garden

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Price per night from

$396

Beautiful Home - Great Price, Wi Fi, Flat Screen

Yarmouth house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Garden

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Price per night from

$201

Cape Cod 2 BD cottage (June $1200wk) private beach in W. Hyannisport

West Hyannisport house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Our family enjoyed a memorable reunion week in this beach neighb” We spent the week walking to aves, swimming at Squaw Island, golfing, tennis, and dining out at some great restaurants. This beach house has central air, a new gas grill and outdoor shower. All musts for our vacation rental requests. Nice quiet area with great Cape Cod experiences. The house is clean and comfortable. Great master bed. Near boats to the vineyard and Nantucket. We plan on another family reunion vacation at this beach house again this summer.

Match: Garden

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Price per night from

$264

Charming 3br Getaway in Oak Bluffs

Oak Bluffs house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Garden

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Price per night from

$344

Dennis Port walk to beach!

Dennis Port house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 7

“Adorable beachy cottage” Wonderful little cottage. Comfortable slept 4 of us, all the conveniences of home but must bring your own linens/towels/washcloths. Great location, walk to beach, good restaurants. Fireplace provided good heat.

Responds fast! avg. 1 hour 26 minutes

Match: Garden

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Price per night from

$230

Responds fast! avg. 24 minutes

Match: Garden

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Price per night from

$287

“A thoroughly enjoyably experience!” Dave was wonderful to work with and offered advise on where some of the best areas to kayak might be found... saw several ospreys and other wildlife. The cottage has all new appliances and was clean. Sitting on the waterfront in the morning with coffee and the afternoon with a toddy was a great way to start and end each day.

Match: Garden

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Price per night from

$344

Falmouth Heights steps to Beaches...Clean and Comfortable

Falmouth house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Garden

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Price per night from

$574

Classic, Quiet, Private Dennisport Cottage

Dennis Port cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

“Perfect Cape Cod Vacation Cottage” We just returned from our week-long stay at this beautiful, immaculately clean cottage. We fell in love with it online, and it certainly did not disappoint! I can honestly say that there was not one thing lacking from this home. Everything we needed was included; just bring some food and a bathing suit and have a great time! The cottage was the perfect size for our family of four, and the family and friends that joined us on the beach for a day all loved the coziness and décor as much as we did. The ocean is a short walk away, but we bought a parking pass for the week, and were happy that we did. Although we did not explore as many different beaches as we thought we might, it was so convenient to have the pass and be able to pack all our things in the car, drive down to Inman Beach, and have the option to make quick (5 minute) trips back to the house for extra drinks/snacks, bathroom breaks, etc. Parking was never an issue at Inman, so there was no concern about losing a spot. Also, don’t miss out on picking up some steamers from George’s Fish Market. We ate them on the back deck after long days on the beach – perfect and delicious! We can’t wait to return next summer, thank you Lynn and Mark for sharing your home with us!

Match: Garden

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Price per night from

$287

Walk to Beach from 4 Bedroom Falmouth Village Home

Falmouth house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Garden

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Price per night from

$516

Unique & Private 3 Bedroom Brewster Home

Brewster house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Garden

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Price per night from

$328

Cape Cod -Falmouth - Beachfront Olde Cape Cod Charm

Falmouth house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 9

Match: Garden

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Price per night from

$501

Crows Nest @ Captain Alexander's Hideaway

West Harwich house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

“Great place to stay and play” A great place to stay for a vacation on Cape Cod. The rooms were comfortable and of good size. There was a relaxing atmosphere and all the comforts of home. Plenty of games and videos for adults and kids and a large screen TV. Parking was ample and easy to come and go. The kitchen was more than expected. The back yard and spacious rear deck and furnishings made outdoor meals and barbecuing a pleasure. I especially liked the covered outdoor shower (with hotwater) to wash away beach sand and ocean salt. Speaking of ocean salt, the beach is just a short walk away.

Match: Garden

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Price per night from

$115

Expansive Cape Get Away - The Grey Whale Awaits!

Cotuit house

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 24

Match: Garden

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Price per night from

$1,310

Great Location, Beautiful Home

Oak Bluffs house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Match: Garden

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Price per night from

$738

Walk to Multiple Beaches and Downtown

Wareham house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

Match: Garden

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Price per night from

$77

Ocean, lake, harbor & parkview Vineyard cottage w/AC and auto ferry tics

Oak Bluffs cottage

  • 6 bedrooms
  • 3 bathrooms
  • sleeps 10

Match: Garden

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Price per night from

$1,147

Private Home with 2 MBRs on Private Road and Beach

Barnstable house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 8

Match: Garden

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Price per night from

$574

Immaculate SeaView Beach House in S.Yarmouth

South Yarmouth house

  • 5 bedrooms
  • 2 bathrooms
  • sleeps 10

Match: Garden

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Price per night from

$573

Captain's Quarters @ Captain Alexander's Hideaway

West Harwich house

  • 1 bathroom
  • sleeps 2

Match: Garden

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Price per night from

$115

Two Wing Cottage - escape with family and friends

Harwich Port cottage

  • 4 bedrooms
  • 5 bathrooms
  • sleeps 10

Match: Garden

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Price per night from

$1,434

Home Away From Home

South Dennis cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

“South Dennis House” The house we rented was perfect for my family. My girls were happy they each had their own bed! The house had everything we needed. We enjoyed the short travel time to all of the Dennis area beaches. The owners were very friendly and helpful. We had a wonderful time.

Responds fast! avg. 2 hours 18 minutes

Match: Garden

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Price per night from

$246

Charming Lambert's Cove Beach House

West Tisbury house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Match: Garden

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Price per night from

$430

Great Place for a Cape Cod Vacation

Barnstable cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

Match: Garden

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Price per night from

$1,147

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