Search Holiday Rentals in Osterville

Start date: Check-in selected.
To Date
End date: Check-out

  • 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
9 Jan - 11 Jan
In two months
20 Feb - 22 Feb
In three months
20 Mar - 22 Mar
In four months
17 Apr - 19 Apr

Our top choices for Osterville holiday rentals

Private beach nearby, beach bar
The Club at New Seabury

The Club at New Seabury

The Club at New Seabury
3.5 star property
New Seabury
9.0 out of 10, Wonderful, (340)
"Very relaxing, loved the different clubs available; beach, pool, tennis, playground for the little ones, bars and food. Some shops were closed due to being off season, but still enjoyed our stay. Looking forward to booking again "
United States
Jose O.
The Club at New Seabury
On the beach, white sand
InnSeason Resorts Captain's Quarters

InnSeason Resorts Captain's Quarters

InnSeason Resorts Captain's Quarters
3.5 star property
Falmouth Heights
9.8 out of 10, Exceptional, (192)
"Great property! Would definitely stay again."
United States
Brad
The price is ฿4,635
฿5,305 total
includes taxes & fees
7 Jan - 8 Jan 2026
InnSeason Resorts Captain's Quarters
Indoor pool, outdoor pool
Brewster Green Resort

Brewster Green Resort

Brewster Green Resort
3.5 star property
Brewster
9.4 out of 10, Exceptional, (121)
"Loved your location. We were originally placed in one of the townhomes, but when the locks/key didn't work, we were upgraded to the stand-alone house #106, which was wonderful! We loved the entire house - kitchen was great and stocked perfectly and all the rooms were big and comfortable. We hope to be back again soon!"
United States
Kathleen
The price is ฿5,568
฿6,373 total
includes taxes & fees
25 Dec - 26 Dec
Brewster Green Resort
Indoor pool, outdoor pool, pool loungers
Sea Mist Resort

Sea Mist Resort

Sea Mist Resort
3.0 star property
Mashpee
8.6 out of 10, Excellent, (144)
"Just there for one night but very enjoyable stay."
United States
Shawna
The price is ฿4,457
฿5,101 total
includes taxes & fees
29 Dec - 30 Dec
Sea Mist Resort
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

Margaritaville Resort Cape Cod

Margaritaville Resort Cape Cod

10/10 Excellent
"Yes"
Kelsey 1-night trip
Posted 5 days ago
Margaritaville Resort Cape Cod

Find out more about Osterville

Search for holiday rentals in Osterville on Expedia! You can easily find your home rentals, villas, holiday apartments in Osterville using one of the methods below:

  • View our selection of featured holiday rentals in Osterville
  • Use the map to find apartments and other holiday homes in the Osterville neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Osterville while they last

Look no further and take a look at our great range of rental properties in Osterville!

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 53 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.