Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

Apartments
Bungalows
Cottages
Estates
Homes
Studios
Barns
Boats
Cabins
Castles
Chalets
Condos
Farmhouses
Hotels
Lodges
Townhomes
Villas
Yachts

Location Type

Even More Filters

Features

Managed By

Cancel Clear Filters Apply Filters
Use filters to narrow your search results!

Osterville Vacation Rentals(45)

45 Results
7 night minimum stay
  • 4 BR,
  • 2 BA,
  • Sleeps 11
(3)
$8,250
per month
31 night minimum stay
  • 4 BR,
  • 2 BA,
  • Sleeps 7
$2,900 - $3,900
per week
7 night minimum stay
  • 3 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 8
(4)
3 - 14 night minimum stay
  • 5 BR,
  • 5 BA,
  • Sleeps 12
1 Review
7 night minimum stay
  • 4 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
1 Review
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 10
1 Review
7 night minimum stay
  • 5 BR,
  • 3 BA,
  • Sleeps 8
2 Reviews
7 night minimum stay
  • 3 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 11
7 night minimum stay
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
$229 - $250
per night
3 - 7 night minimum stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
2 night minimum stay
  • 1 BR,
  • 1 BA,
  • Sleeps 2
(9)
7 night minimum stay
  • 2 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 4
3 - 7 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 8
(5)
7 night minimum stay
  • 6 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
1 Review
7 night minimum stay
  • 3 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 10
7 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 5
1 Review
14 night minimum stay
  • 4 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 8
2 Reviews
7 night minimum stay
  • 3 BR,
  • 1 BA,
  • Sleeps 6
2 - 7 night minimum stay
  • 2 BR,
  • 1 BA,
  • Sleeps 4
(4)
3 - 7 night minimum stay
  • 5 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 10
1 Review
7 night minimum stay
  • 4 BR,
  • 2 BA,
  • Sleeps 12
1 Review
7 night minimum stay
  • 4 BR,
  • 2 BA,
  • Sleeps 8
$1,000 - $2,600
per week
7 night minimum stay
  • 4 BR,
  • 2 BA,
  • 1 HF BA,
  • Sleeps 8
7 night minimum stay
  • 4 BR,
  • 3 BA,
  • Sleeps 8
6 night minimum stay
  • 6 BR,
  • 4 BA,
  • 1 HF BA,
  • Sleeps 14
  • 3 BR,
  • 4 BA,
  • Sleeps 10
7 night minimum stay
  • 2 BR,
  • 2 BA,
  • Sleeps 5
(5)
16 more choices from the HomeAway Network
4 - 7 night minimum stay
  • Studio,
  • 1 BA,
  • Sleeps 2
(7)
Advertisement
 

Recent Osterville Reviews

Beautiful and spacious Osterville/Cape home

5 of 5
A great home for a wonderful vacation. Located in the town of Osterville, the home is a short walk to the downtown area of shops, restaurants and stores. Fancy's market has a nice little selection of groceries, wine and beer. Better yet, order some sandwiches and deli salads to take home or on a picnic. You also have access to the nearby resident beach that is a long walk or short ride from the home. Hyannis is a very scenic 10 minute drive . Plenty of shops and restaurants there to explore, The home is very comfortable for a larger group, There is a nice and spacious family/living room at the front of the house and a separate television room off the large dining room. The five bedrooms were perfect for a varied crowd. My parents stayed in the separate second master. Our daughter attends college in Boston so she had two friends come down and stay with us on separate days. We cooked in two nights, which was a breeze since the kitchen is well stocked with just about any pot, pan or utensil you need. The outdoor grill was great and is hooked up to city gas. It was clean and the grill utensils were new. Great fire pit outside and the s'mores couldn't have been better. Everyone of our group loved the experience; from 12 to 74. As for the owners, Kristen and Rich, they could not have been more helpful and accommodating. Everything was as promised. I mentioned to Kristen that we were there to celebrate our daughter's 21st birthday. The first thing we see as we all enter the Kitchen is a bouquet of flowers with a happy birthday note for our daughter. First class all the way. I recommend a stay here if you have a chance. If I get a chance to go back to the Cape, that's where I'll be.
  • Submitted: Aug 7, 2014
  • Stayed: Jul 2014

perfect in every way

5 of 5
we were 3 couples enjoying an adult week on the Cape. the town itself is quaint and has great restaurants. we ate at a place called Wimpys, not to be missed. the house has everything you would need including a hot tub which we could not get the golfing husbands out of. Everthing from china to mattresses was tops. we walked to the beach which we had to ourselves since it was september and it was a beautiful place for watching the sunset. the owner was responsive to our requests and the property was spotless.
  • Submitted: Jan 22, 2014
  • Stayed: Sep 2013

Delightful decor and charmingly comfortalbe

5 of 5
This is a gem of a rental for a family that prizes exceptional comfort in a style that suggests a New England version of "Southern Living." Having spent many years in Osterville, my husband and I were delighted to see the pictures of this lovely home with its tasteful décor and sunlit rooms. The owner attended to our every need; he offered useful suggestions and local lore gained from his many years in the area. We were amazed at the spaciousness of every room. The master bedroom, with its walk-in closet, and the guest bedrooms are not only lovely, but also each has its own full bathroom. Although the weather in early June was rainy, with so many rooms, we found our family and ourselves entirely comfortable. Strolling the charming main street, as we often had many years ago, we found the new library a delightful and useful attraction. However, the best of the town hadn’t changed -nestled between salt-water bays, Osterville offers not only charm but a beach and a lovely golf course. For anyone who is hoping to rent an enchanting, spacious home in one of the Cape’s most charming towns, this is a wonderful choice.
  • Submitted: Oct 1, 2013
  • Stayed: Jun 2013