Osterville Rentals

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1,080 Houses

271 Westwind Cir

Osterville house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

Price per night from

$220

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

$1,031

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

Cliff Cottage By The Pond

Dennis house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$148

Excellent location on Martha's Vineyard

Edgartown house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$630

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

$1,309

Raised Split Ranch Single House in South Dennis

Dennis house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$401

Price per night from

$781

101 Ploughed Neck Rd

East Sandwich house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

Price per night from

$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.

Price per night from

$456

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

$1,637

Glendon Beach Cottage #95 100 yds to the beach

Dennis house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

“Long Weekend” Great location to beach and local places to eat and drink. Easy access to the rest of the Cape. Pet friendly was a plus. The only downer was it stated it slept 6 but only room for 4, this made for some unhappy campers

Responds fast! avg. 8 minutes

Price per night from

$201

100 Wing Blvd East

East Sandwich house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

Price per night from

$320

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

$630

58 Carman Ave

Sandwich house

  • 4 bedrooms
  • 1 bathroom
  • sleeps 8

Price per night from

$240

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

$315

Charming 3 Bedroom Colonial In Popponesset

Mashpee house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

Price per night from

$843

Contemporary 4 Bedroom House One Mile to Beach

New Seabury house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 7

Price per night from

$829

Renovated Cape Cod Home -10 Minutes To Beaches & Ctr

Hyannis Port house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 7

Price per night from

$370

Beachland 12

East Sandwich cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

“Perfect for our Family!” We have stayed in many cottages in East Sandwich and this one is by far our favorite. The view off the back deck is beautiful. It was wonderful having coffee out there in the morning. Also, the breeze you get coming off the marsh is wonderful. The cottage was clean and bright and was perfect for our family of 4! We can't wait to come back and stay again and again and again!

Price per night from

$150

131 North Shore Blvd Unit 7

East Sandwich apartment

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Price per night from

$170

Beachland H

East Sandwich cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

“It was great to be near the beach.” Lovely cottage that was perfect for a family of four. The kids enjoyed being able to walk to the beach. The cottage had everything (kitchen stuff, beach chair, BBQ, etc.). The town of Sandwich is a quiet location.

Price per night from

$114

Beachland K

East Sandwich cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$150

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!!! : )

Price per night from

$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.

Price per night from

$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.

Price per night from

$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.

Price per night from

$340

5 Captain Crocker

East Sandwich cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 7

Price per night from

$857

103 North Shore Blvd unit 3

East Sandwich apartment

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$157

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.

Price per night from

$270

Viewing 38 of 1,080
rentals in Osterville

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