Osterville Rentals

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775 Houses

271 Westwind Cir

Osterville house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

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$220

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

Osterville apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

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$523

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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Price per night from

$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

Cliff Cottage By The Pond

Dennis house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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$148

In the Heart of Brewster. Min to Bay Beaches

Brewster house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

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$493

Raised Split Ranch Single House in South Dennis

Dennis house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$401

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$781

101 Ploughed Neck Rd

East Sandwich house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

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$250

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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Price per night from

$1,637

100 Wing Blvd East

East Sandwich house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

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Price per night from

$320

4 Bedroom Cape with Swimming Pool

Dennis house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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$602

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

99B North Shore Blvd

East Sandwich cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

“Wonderful” Our stay at north shore Blvd was wonderful. The view was spectactular, the location was great and the house was very nice. There was a small issue of previous damage with the refrigerator drawer, but we called the office right away and reported it to them. Would I rent this location again? Absolutely!!! : )

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$279

Oceanside B

East Sandwich cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 6

“outstanding” the house is great, always a pleasure to stay here. the office staff at sand dollar are always pleasant and handled any concerns i had positively which made are trip that much more enjoyable. be back next year.

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$214

99 North Shore Blvd

East Sandwich house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Ideal family cottage” We have stayed in tis cottage for the past few years and it is ideal for our family set up (mother downstairs us and kids upstairs) and is a good value for the price. Although not ocean front it's close enough that it doesn't bother us. We needed to call Sand Dollar because there was no propane tank and they made sure to bring us one the next day. The back entrance was totally overgrown with shrubs and bushes and could not be used-they brought us small pruning shears but they weren't big enough to do the job so hopefully was taken care of for the next renters coming in. The cottage was very clean upon chek in. Overall a very nice vacation and we plan to stay here again next summer.

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$200

14 Captain Crocker

East Sandwich house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

“Loved it!” We loved this house. It's right on the beach, it's private, and the sunsets are beautiful (and different each night). We loved being able to let our kids play on the beach while we watched them from the deck with our coffee. Not having to lug everything but the kitchen sink down to the beach was a huge bonus. If we needed to use the restroom, get a snack, or take a break from the sun, the house was right there. We would definitely stay here again.

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$340

343 Phillips Rd

Sagamore Beach cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 5

“Beautiful ocean front cottage” Just a small walk to a private beach. You do not have to sit in hours of traffic to go over the bridge to enjoy being at the cape.

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$270

14 Benedict Rd

Bourne house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

“Never Bored in Bourne” This three bedroom home on a tree lined secluded lot offers spectacular views! A large deck facing lush, green tidal pools offer relaxing views. Kitchen/Dining area with loads of counter space allow for lots of family cooking and dining. We had a great time !

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Price per night from

$214

177A North Shore Blvd

East Sandwich cottage

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

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Price per night from

$171

93 Phillips Rd

Sagamore Beach house

  • 7 bedrooms
  • 3 bathrooms
  • sleeps 15

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Price per night from

$357

115 North Shore Blvd

East Sandwich house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

“Good place for families” Very nice place, great beachfront and waterside deck. Good spot for families, if the kids are not too little. (The lack of railings on the deck might be a worry for very small kids.) Centrally located if you want to take day trips to Martha's Vineyard, Plymouth, Boston and the outer Cape like we did. The house is showing some minor signs of wear and tear as a rental. For the extra $50 or $100 it might add to the rent, I'd prefer to have it professionally cleaned between visits rather than relying on the guests to do it. (I don't mind cleaning up after myself, but you can't rely on the previous guests to meet any kind of standard.) It would have been nice to have an empty cupboard for our week's groceries. Instead, the cupboards were full of packaged foods left behind and way more dishes and glasses than you could ever need. All minor complaints meant mainly for management company and owner to consider.

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$420

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.

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$132

3 Clark St

Sandwich farmhouse

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

“clean comfortable and close to the beach” I cant say enough about the summer home. We will be going again and again. It is so comfortable, clean and close to the beach and boardwalk. Thank you owners and sand dollar realty for a great vacation!

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$210

165 North Shore Blvd

East Sandwich cottage

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

“Love the Two-Family Capability of This Property!” We stayed here the last week of June and it was fantastic! Our family of four (with two small sons) stayed in the side cabin while my in-laws stayed in the larger home. It couldn't have been more perfect. Both homes were immaculate and well-stocked (dishes, pots, pans, flatware) so we were able to cook full meals during our stay. Our favorite part of our week was the amazing beach. Our boys waited each day for the sandbars to appear, and then would spend hours playing ball and wading in the cold bay water. We appreciate the owners sharing their lovely property with us and would be honored to stay there again in the future!

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$310

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.

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$210

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.

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$229

62 Knott Ave

Sandwich cottage

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

“good family fun!!!” Th service from Sand dollar Realty was great! They took care of every thing from check in/out times, where to pick up house keys, directions to thier office, to the vacation rental and a host of resources for us to explore. They went to great lengths to reduce as much stress as possible to help make our vacation a wonderful experiance. We absolutely loved the home! It was perfect for our family of five. We were very comfortable, the home was immaculate, had all the ameneties of any home, great layout, and plenty of space. We were pleasantly surprised upon arrival to see aC in the windows. That was a bonus for us because it was not mentioned in the amenities on the web site. It was a great relief because my wife is 7 months pregnant. There were plenty of cookware, utensils, all the appliances worked super, and extra bed blankets. The location and local amenities were perfect. Everything was with in a very short walking, riding, or driving distance. We walked and road our bikes to the beaches, board walk,(Awsome!!), and Cape Cod Canal. There were great resturaunts, Ice cream shops, grocer stores, bait shops, and banks all with in minutes. What we liked best. It felt like we were at our very own beach house. We felt relaxed, comfortable, had no worries, or stress. The owners left great welcoming gifts and information on sights, places to eat and local atractions. We loved the location, house, the towns histoy, local shops, board walk and the marsh at low tide. What we liked least. The shower head is to low. I had to squat to get under it and I'm just barely 6ft tall. A hand held shower head might be good option. Also the TV was small. I'm guessing 15 - 19inch screen. Overall, we had a great time and wished we could have stayed longer. We would like to thank Sand Dollar Realty for all their support and assistance with making the stay worry free. We would also like to thank the home owners for sharing their home with us.

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$257

40 Ploughed Neck Rd

East Sandwich house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$540

18 Great Hill Rd.

Sandwich house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$171

Quarterboard 4

East Sandwich cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$120

9 Turtle Cove Rd

East Sandwich cottage

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$200

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

Oak Bluffs house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 19

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Price per night from

$6,870

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