Osterville Rentals

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1,070 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

$1,030

236B Smoke Valley Road 153791

Osterville house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 5

Price per night from

$486

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

Solera Victorian charm, ocean view, steps to beach

Oak Bluffs cottage

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 9

Price per night from

$1,960

Seaside cottage

Falmouth cottage

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 4

Price per night from

$491

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

New Seabury house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

Price per night from

$372

3bd 2 bath steps to private association beach

Dennis Port house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 7

“Beautiful Location” Loved the house and will stay again in this location House was decorated beautifully. Very clean and a the beach was clean and lovely . Short distance to shops , restaurants and activities

Price per night from

$621

Antique Captain's Home in the Heart of Dennisport

Dennis Port house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 6

Responds fast! avg. 3 hours 14 minutes

Price per night from

$115

Cape Cod Charm in Falmouth Village

Falmouth studio

  • Studio
  • 1 bathroom
  • sleeps 4

Price per night from

$372

Excellent location on Martha's Vineyard

Edgartown house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$629

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

Responds fast! avg. 17 minutes

Price per night from

$492

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

Barnstable house

  • 3 bedrooms
  • 4 bathrooms
  • sleeps 8

Price per night from

$1,307

Price per night from

$780

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

$523

2 BR Cape Cod Vacation Rental

Mashpee house

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$1,635

4 Bedroom Cape with Swimming Pool

Dennis house

  • 4 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$588

Waterfront, Quiet 3 BR Cape-Walk to Beach

Falmouth house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 8

Price per night from

$629

High End-suite style cottage 5 min bike ride to amazing Craigville Beach.

Centerville cottage

  • 1 bedroom
  • 1 bathroom
  • sleeps 2

Responds fast! avg. 19 minutes

Price per night from

$343

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

$842

Contemporary 4 Bedroom House One Mile to Beach

New Seabury house

  • 4 bedrooms
  • 3 bathrooms
  • sleeps 7

Price per night from

$828

Renovated Cape Cod Home -10 Minutes To Beaches & Ctr

Hyannis Port house

  • 3 bedrooms
  • 1 bathroom
  • sleeps 7

Price per night from

$370

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

$370

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

Oak Bluffs house

  • 5 bedrooms
  • 5 bathrooms
  • sleeps 19

Price per night from

$6,862

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

$263

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

$629

“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

$395

Price per night from

$732

Beautiful Home - Great Price, Wi Fi, Flat Screen

Yarmouth house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$201

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.

Price per night from

$263

Charming 3br Getaway in Oak Bluffs

Oak Bluffs house

  • 3 bedrooms
  • 2 bathrooms
  • sleeps 6

Price per night from

$343

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 21 minutes

Price per night from

$229

High-end Brewster ,Mass. Bay view town home

Brewster apartment

  • 2 bedrooms
  • 2 bathrooms
  • sleeps 5

Price per night from

$409

Viewing 38 of 1,070
rentals in Osterville

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