Osterville Rentals

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915 Houses

271 Westwind Cir

Osterville house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 6

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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

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Price per night from

$523

OSTERVILLE VILLAGE NEWLY RENOVATED ON 6 ACRES CLOSE TO BEACHES

Osterville house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$1,031

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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Price per night from

$224

Great rentals within 20 miles that match your search

Popponesset Beach-Mashpee, MA. 4 minute walk to pristine beach.

New Seabury house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

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Price per night from

$373

3bd 2 bath steps to private association beach

Dennis Port house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

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Price per night from

$622

Excellent location on Martha's Vineyard

Edgartown house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$630

In the Heart of Brewster. Min to Bay Beaches

Brewster house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

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Price per night from

$493

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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Price per night from

$456

Beautiful vacation home for rent

Dennis house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$524

2 BR Cape Cod Vacation Rental

Mashpee house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

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Price per night from

$1,637

4 Bedroom Cape with Swimming Pool

Dennis house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$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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Price per night from

$344

Charming 3 Bedroom Colonial In Popponesset

Mashpee house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

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Price per night from

$843

Renovated Cape Cod Home -10 Minutes To Beaches & Ctr

Hyannis Port house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 7

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Price per night from

$370

Magnificent Contemporary on Exclusive Point

Falmouth house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

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Price per night from

$916

2 min walk to the beach - 30 Union Wharf#3

Dennis Port condo

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$287

28-2 Greyneck Road Harwich MA

West Harwich condo

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

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Price per night from

$516

Charming 2 bdrm 1 1/2 bath house

Dennis Port house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

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Price per night from

$194

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

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Price per night from

$245

Nice clean house 1/4 mile walk to Sesuit Harbor!

Dennis house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

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Price per night from

$516

Quintessential Cape Cod

West Yarmouth house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

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Price per night from

$745

Great Place for a Cape Cod Vacation

Barnstable cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

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Price per night from

$1,145

Quaint 2 bdrm unit

Dennis Port house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

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Price per night from

$228

Sweet Cottage in Woods Hole Village Steps to Beach

Woods Hole cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 5

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Price per night from

$430

Ocean View Condo across from Beach with pool!

Dennis Port condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 26 minutes

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Price per night from

$172

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Price per night from

$395

Chatham Beach Chic 5⭐ -5 min Walk to Beach! Cape Escape Hear the waves at Night!

South Chatham house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 10

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Price per night from

$395

Solera Victorian charm, ocean view, steps to beach

Oak Bluffs cottage

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

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Price per night from

$1,963

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!

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Price per night from

$370

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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Price per night from

$264

“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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Price per night from

$395

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Price per night from

$733

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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Price per night from

$264

Charming 3br Getaway in Oak Bluffs

Oak Bluffs house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

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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

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Price per night from

$229

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