Osterville Rentals

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810 Houses

271 Westwind Cir

Osterville house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

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$220

236B Smoke Valley Road 153791

Osterville house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

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$464

Contemporary Gem with Private Pool!

Osterville house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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$402

Walk to Joshua Pond Beach & Downtown!

Osterville house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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$224

Great rentals within 20 miles that match your search

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$781

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.

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$456

2 BR Cape Cod Vacation Rental

Mashpee house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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$1,637

4 Bedroom Cape with Swimming Pool

Dennis house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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$589

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

Centerville cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

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$344

3 bedroom 2 bath Fully remodeled home

Falmouth house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$315

Charming 3 Bedroom Colonial In Popponesset

Mashpee house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

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$843

Contemporary 4 Bedroom House One Mile to Beach

New Seabury house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 7

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$829

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

Oak Bluffs house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 19

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$6,870

Vineyard Haven Guest House - Sleeps 4, A/C, Walk to Town

Vineyard Haven house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

“great stay in Vineyard Haven” We enjoyed staying in David's guest house. It was clean, well situated (a short walk from downtown Vineyard Haven), and made for a relaxing few days on the Vineyard. David was easy to reach and very responsive to any of our needs. I would highly recommend you stay at the guesthouse.

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$264

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.

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$630

“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!!!

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$395

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$733

Beautiful Home - Great Price, Wi Fi, Flat Screen

Yarmouth house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$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.

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$264

Charming 3br Getaway in Oak Bluffs

Oak Bluffs house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$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

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$229

High-end Brewster ,Mass. Bay view town home

Brewster apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

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$409

Clean, comfortable ranch with lots of amenities

Oak Bluffs house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

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$544

Responds fast! avg. 24 minutes

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$287

Falmouth Heights steps to Beaches...Clean and Comfortable

Falmouth house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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$573

Oak Bluffs Contemporary Summer Home

Oak Bluffs house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$360

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!

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$287

Walk to Beach from 4 Bedroom Falmouth Village Home

Falmouth house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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$516

Former Chatham Bed and Breakfast

Chatham b&b

  • 6 bedrooms
  • 5 bathrooms
  • sleeps 12

“Classic cape cod experience” Beautiful property well located on the cape non commercial sector. Tastefully appointed overall fantastic.

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$638

Unique & Private 3 Bedroom Brewster Home

Brewster house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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$328

Cape Cod -Falmouth - Beachfront Olde Cape Cod Charm

Falmouth house

  • 5 bedrooms
  • 3 bathrooms
  • sleeps 9

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$500

Cape Cod 2 BR Condo at the Beach August 5-12 !

Dennis Port hotel apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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$245

Timeshare rental Cove at Yarmouth, Cape Cod, MA

West Yarmouth hotel apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

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$184

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.

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$115

Expansive Cape Get Away - The Grey Whale Awaits!

Cotuit house

  • 7 bedrooms
  • 5 bathrooms
  • sleeps 24

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$1,308

Great Location, Beautiful Home

Oak Bluffs house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$737

Walk to Multiple Beaches and Downtown

Wareham house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

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$77

Ocean, lake, harbor & parkview Vineyard cottage w/AC

Oak Bluffs cottage

  • 6 bedrooms
  • 3 bathrooms
  • sleeps 10

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Price per night from

$1,145

Viewing 38 of 810
rentals in Osterville

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