A house by a lake with boats.

Search Holiday Rentals in Osterville

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
11 Sep - 13 Sep
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Osterville holiday rentals

Private beach nearby, beach bar

1. The Club at New Seabury

The Club at New Seabury
3.5 star property
New Seabury
9.0 out of 10, Wonderful, (367 reviews)
"Overall, very good. Pool and beach area were not the most convenient to access. Short drive required."
United States
Grayson
The price is 5.280.394 ₫
6.043.411 ₫ total
includes taxes & fees
7 Sept - 8 Sept
The Club at New Seabury
Front of property

2. Holly Tree Resort

Holly Tree Resort
3.0 star property
West Yarmouth
9.2 out of 10, Wonderful, (409 reviews)
"Was really good place"
United States
Philip
The price is 6.994.393 ₫
8.005.083 ₫ total
includes taxes & fees
30 Aug - 31 Aug
Holly Tree Resort
Indoor pool, seasonal outdoor pool

3. The Cove at Yarmouth by Westgate Resorts

The Cove at Yarmouth by Westgate Resorts
3.0 star property
West Yarmouth
9.2 out of 10, Wonderful, (268 reviews)
"P Indoor pool and hot tub loved and the outdoor Shack was great"
United States
BELKIS
The price is 4.553.655 ₫
5.211.660 ₫ total
includes taxes & fees
24 Sept - 25 Sept
The Cove at Yarmouth by Westgate Resorts
House (3 Bedrooms) | Interior

4. Bike to Beach: Centerville Home w/ Deck!

Bike to Beach: Centerville Home w/ Deck!
3.0 star property
Centerville
Bike to Beach: Centerville Home w/ Deck!
Miscellaneous

5. Sal's Place

Sal's Place
2.0 star property
Hyannis
The price is 16.976.050 ₫
22.563.260 ₫ total
includes taxes & fees
20 Sept - 21 Sept
Sal's Place
Private beach

6. Edgewater Beach Resort

Edgewater Beach Resort
3.5 star property
Dennis Port
9.0 out of 10, Wonderful, (338 reviews)
"Great place! Everything was lovely"
United States
Susan
The price is 7.294.478 ₫
8.348.531 ₫ total
includes taxes & fees
30 Aug - 31 Aug
Edgewater Beach Resort
Indoor spa tub

7. Brewster Green Resort

Brewster Green Resort
3.5 star property
Brewster
9.4 out of 10, Exceptional, (141 reviews)
"Clean, good activities for the kids and pools were nice"
United States
Jim
The price is 5.719.623 ₫
6.546.109 ₫ total
includes taxes & fees
24 Sept - 25 Sept
Brewster Green Resort
Cottage (2 Bedrooms) | Interior

8. Walk to Swift's Beach! Classic Cottage w/ Deck

Walk to Swift's Beach! Classic Cottage w/ Deck
3.0 star property
Wareham
10.0 out of 10, Exceptional, (1 review)
"3 of us had a great time in Wareham. The cottage was exactly as advertised and close to many beaches"
United States
Tracy
The price is 5.171.166 ₫
13.448.949 ₫ total
includes taxes & fees
30 Aug - 31 Aug
Walk to Swift's Beach! Classic Cottage w/ Deck
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Osterville Hotel Reviews

Uncommoner Hotel by Reverie Boutique Collection

Uncommoner Hotel by Reverie Boutique Collection

8/10 Good
"Friendly, helpful staff and very clean and beautifully decorated rooms."
Paul 2-night trip
Posted 1 hour ago
Uncommoner Hotel by Reverie Boutique Collection

Frequently asked questions

Can I find holiday rentals in Osterville?

Yes, there are holiday rentals in Osterville close to Stand Up & Paddle Cape Cod, or you can select a more secluded option if you're looking for a relaxing stay.

How many holiday rentals are there in Osterville?

With 59 Expedia holiday rentals, you're guaranteed to find just the right place for your Osterville stay.

What’s there to see and do in Osterville?

Cape Cod Beaches and Dowses Beach are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Stand Up & Paddle Cape Cod. Public Beach and Main Street are a couple of places you'll find in the wider area.

What’s a holiday rental in Osterville like?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Osterville. Holiday rentals offer extras like WiFi and washers and dryers so you'll have a home away from home. If you're concerned about cleanliness, a holiday rental can offer a sense of privacy away from public hotel lifts and lobbies packed with people while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great option for a family trip or a small group gathering.