Osterville Rentals

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1,081 Houses

271 Westwind Cir

Osterville house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

Price per night from

$221

Walk To Joshua Pond & Main St. 2 Bedroom Cottage, Central Cape Location

Osterville apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

Price per night from

$523

OSTERVILLE VILLAGE NEWLY RENOVATED ON 6 ACRES CLOSE TO BEACHES

Osterville house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$1,032

236B Smoke Valley Road 153791

Osterville house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

Price per night from

$464

Contemporary Gem with Private Pool!

Osterville house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$402

Walk to Joshua Pond Beach & Downtown!

Osterville house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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

Price per night from

$631

Connors Cottage

West Hyannisport house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

Price per night from

$201

In the Heart of Brewster. Min to Bay Beaches

Brewster house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

Price per night from

$493

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

Barnstable house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

Price per night from

$1,311

Price per night from

$782

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.

Price per night from

$457

Beautiful vacation home for rent

Dennis house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Price per night from

$524

2 BR Cape Cod Vacation Rental

Mashpee house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$1,639

4 Bedroom Cape with Swimming Pool

Dennis house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$602

Waterfront, Quiet 3 BR Cape-Walk to Beach

Falmouth house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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

Price per night from

$344

3 bedroom 2 bath Fully remodeled home

Falmouth house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$316

Charming 3 Bedroom Colonial In Popponesset

Mashpee house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

Price per night from

$844

Contemporary 4 Bedroom House One Mile to Beach

New Seabury house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 7

Price per night from

$831

Renovated Cape Cod Home -10 Minutes To Beaches & Ctr

Hyannis Port house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 7

Price per night from

$371

103 North Shore Blvd unit 3

East Sandwich apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$158

173C North Shore Blvd

East Sandwich cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

“Great cottage! Clean, updated, cair, laundry, outside shower. Hi” This is a wonderful a very comfortable cottage. Great for a family of up to 5. Very modern, hardwood floors, central air, laundry, storage space for bikes, fishing equipment, etc. Quick walk to a very quiet beach. The low tides are awesome! Surrounding cottages are very nice. The town of East Sandwich is very quiet. Great restaurants, ice cream, antiques, etc.

Price per night from

$211

34 Salt Marsh Rd

East Sandwich cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

“Perfect Cape Vacation Experience” This was a waterfront property with marsh across the street, on a quiet private beach. The photos are very true to life, and the house was well equipped with pots and pans, cups, even bug spray. There were great views from the house, and it was truly relaxing to see and hear the waves from anywhere on the property. The rental company was excellent - key was ready for us, linens and chairs waiting on the porch when we arrived. Very close to 6a - grocery, restaurants, ice cream :) - but also remote location without any public traffic in the neighborhood. I could not have asked for a better house or location for our Cape vacation - we will be returning next year!

Price per night from

$371

Beachland I

East Sandwich cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

“Clean, good location, family friendly” We loved being so close to bay. Very family friendly. Very clean. Would come here again. Our only complaint is the "trundle bed" was not a true trundle with another twin bed under. It was drawers. Thank goodness we brought an extra air mattress!!

Price per night from

$171

Oceanside 1

East Sandwich cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Peaceful” Beauifully decorated very clean house. Great location. Tiny but all we needed! Very quiet area.

Price per night from

$133

Oceanside 3

East Sandwich cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

“Quintessential Cape Cod beach house - yes, the one in your dream” I stayed at this adorable beach house in august of 2011, my first time to beautiful Cape Cod. I could not have imagined it more perfectly; this little cottage is nestled right in the sand, bare foot steps on the beach. Its the perfect size for a couples retreat or a small family. You will feel worlds away from reality in this cozy and comfortable cottage. We enjoyed a fire on the beach, a stroll into East Sandwich for breakfast, many hours lounging in the sun and playing in the sand-bottomed surf. I still dream of this house, and it will always hold a special place in my traveling memories, for it was far too perfect for words. Thank you Jay and Gretchen for sharing your slice of heaven!

Price per night from

$115

89-2 Salt Marsh Rd

East Sandwich cottage

  • 2 bedrooms
  • 3 bathrooms
  • sleeps 6

“A piece of heaven!” This was our second year renting this house. It is airy, comfortable,and it's proximity to the beach is ideal. We really enjoyed the upstairs deck and the living room upstairs. The kitchen is well equipped. We grill a lot and had to fill the propane tank on the grill for the second time this year. That might be something to check before renters arrive. Location is close to shopping, laundry facilities, and restaurants. We didn't leave much because we loved it there. We enjoyed playing games on the beach, and taking daily runs, walks on the road and beach. Plenty of games, puzzles, etc. in the house which our kids took advantage of. We rented kayaks from Ride away Kayaks and they were great- delivered them and picked them up. We kayaked every day. Overall, one of our best vacations. Sand Dollar Realty was great to work with. Very professional, organized, and made arrival and departure very smooth.

Price per night from

$211

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.

Price per night from

$230

18 Great Hill Rd.

Sandwich house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$172

Quarterboard 4

East Sandwich cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$121

Dune Tootin Unit 1

East Sandwich cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

“Life is good!!” We had three generations traveling with us. These cottages were perfect. We had our privacy and we could be together when we wanted. They were well equipped. Location was wonderful. Time just went too fast!!!

Price per night from

$215

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

Oak Bluffs house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 19

Price per night from

$6,880

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.

Price per night from

$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.

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!!!

Price per night from

$396

Price per night from

$734

Beautiful Home - Great Price, Wi Fi, Flat Screen

Yarmouth house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$201

Viewing 38 of 1,081
rentals in Osterville

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