Osterville Rentals

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1,073 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

$522

OSTERVILLE VILLAGE NEWLY RENOVATED ON 6 ACRES CLOSE TO BEACHES

Osterville house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$1,026

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

Responds fast! avg. 2 hours 35 minutes

Price per night from

$273

Walk to Joshua Pond Beach & Downtown!

Osterville house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 6

Responds fast! avg. 2 hours 35 minutes

Price per night from

$224

Great rentals within 20 miles that match your search

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

$342

Charming 3 bdrm cottage - walk to beach

Dennis Port house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

Price per night from

$245

3 bedroom 2 bath Fully remodeled home

Falmouth house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$598

Charming 3 Bedroom Colonial In Popponesset

Mashpee house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 10

Price per night from

$839

Charming 2 bdrm 1 1/2 bath house

Dennis Port house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$193

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. 3 hours 57 minutes

Price per night from

$244

Quintessential Cape Cod

West Yarmouth house

  • 3 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$741

Charming Lambert's Cove Beach House

West Tisbury house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 8

Price per night from

$428

Great Place for a Cape Cod Vacation

Barnstable cottage

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

Price per night from

$1,140

Quaint 2 bdrm unit

Dennis Port house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 4

Price per night from

$227

Sweet Cottage in Woods Hole Village Steps to Beach

Woods Hole cottage

  • 3 bedrooms
  • 1 bathroom
  • sleeps 5

Price per night from

$428

Martha's Vineyard Rental

Edgartown house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$651

Ocean View Condo across from Beach with pool!

Dennis Port condo

  • 1 bedroom
  • 1 bathroom
  • sleeps 4

Responds fast! avg. 1 hour 56 minutes

Price per night from

$171

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

Price per night from

$393

Price per night from

$393

Solera Victorian charm, ocean view, steps to beach

Oak Bluffs cottage

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

Price per night from

$1,953

Seaside cottage

Falmouth cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$489

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

New Seabury house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

Price per night from

$371

3bd 2 bath steps to private association beach

Dennis Port house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

Price per night from

$619

Excellent location on Martha's Vineyard

Edgartown house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$627

In the Heart of Brewster. Min to Bay Beaches

Brewster house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 9

Price per night from

$490

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

Barnstable house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

Price per night from

$1,303

101 Ploughed Neck Rd

East Sandwich house

  • 2 bedrooms
  • 1 bathroom
  • sleeps 5

Price per night from

$249

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

$454

Beautiful vacation home for rent

Dennis house

  • 4 bedrooms
  • 4 bathrooms
  • sleeps 8

Price per night from

$521

2 BR Cape Cod Vacation Rental

Mashpee house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$1,628

4 Bedroom Cape with Swimming Pool

Dennis house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$598

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

$369

3 White Cap Path

Sandwich apartment

  • 1 bedroom
  • 2 bathrooms
  • sleeps 4

“Comfort, breezes, superb views” For older renters this is an ideal setting for walks, long views, easy access to the Canal, route 6a and Sandwich tourist offerings. There's nothing between you and the water - no traffic to negotiate, no noise, no crowds. Do you need a big-screen TV? You've got it.Lots of lounging space? Ditto. Nearness to a market? No problem. A fully-equipped kitchen? It's yours. This is a hidden jewel!

Price per night from

$285

9 Turtle Cove Rd

East Sandwich cottage

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$199

“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

$393

Charming 3br Getaway in Oak Bluffs

Oak Bluffs house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$342

Viewing 38 of 1,073
rentals in Osterville

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