A house by a lake with boats.

Osterville Holiday Rentals

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Our top choices for Osterville holiday rentals

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 NZ$418
includes taxes & fees
8 Sept - 9 Sept
The Club at New Seabury

2. 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 NZ$339
includes taxes & fees
24 Sept - 25 Sept
The Cove at Yarmouth by Westgate Resorts

3. Sal's Place

Sal's Place
2.0 star property
Hyannis
The price is NZ$1,274
includes taxes & fees
7 Sept - 8 Sept
Sal's Place

4. 1 Mi to Ferry: 'sea Street Cottage' in Hyannis

1 Mi to Ferry: 'sea Street Cottage' in Hyannis
3.0 star property
Hyannis
8.0 out of 10, Very good, (1 review)
"The cottage is in a great location close to Main Street and the harbor. Easy parking at the cottage and it’s in a walkable area. Decor is cute and nautical, but it does feel like the cottage is missing a few things. It sleeps 4, but there is not enough seating for 4 in the living room. An additional comfortable chair would be nice. A stackable washer and dryer would also be great, but there is very little space for anything- we even had trouble finding spots for our luggage. The fridge door...
United States
Christa
The price is NZ$618
includes taxes & fees
2 Oct - 3 Oct
1 Mi to Ferry: 'sea Street Cottage' in Hyannis

5. Brewster Green Resort

Brewster Green Resort
3.5 star property
Brewster
9.4 out of 10, Exceptional, (142 reviews)
"Clean, good activities for the kids and pools were nice"
United States
Jim
The price is NZ$426
includes taxes & fees
24 Sept - 25 Sept
Brewster Green Resort

6. 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 NZ$875
includes taxes & fees
8 Sept - 9 Sept
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.
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Top Osterville Hotel Reviews

Find out more about Osterville

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Osterville holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Osterville. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Osterville. Seeing all the best attractions is bound to make you fall in love with Osterville. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Osterville short-term rentals, that won’t be hard to do.

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.

What are some of the best holiday rentals that Osterville has to offer?

Cape Cod's "Beach Rose": This holiday home rental outside of Osterville offers a patio, a selection of games and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family.

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.