A house by a lake with boats.

Osterville Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

Our top choices for Osterville vacation rentals

A coastal hotel with multiple beachside rooms, a large covered area, and a beach with umbrellas.

1. The Club at New Seabury

The Club at New Seabury
3.5 star property
New Seabury
9.0 out of 10, Wonderful, (371 reviews)
"The New Seabury resort is beautiful & has excellent customer service. The 4/5 stars is because the unit we stayed in needs some updating. However, the layout, cleanliness, & location is good."
United States
Kathleen
$202 nightly
The price is $231
Oct 13 - Oct 14
Total with taxes and fees
The Club at New Seabury
A pool area with lounge chairs and flags.

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
$114 nightly
The price is $131
Oct 25 - Oct 26
Total with taxes and fees
The Cove at Yarmouth by Westgate Resorts
A compact living space with a kitchen, dining area, and seating area.

3. 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
$318 nightly
The price is $364
Oct 2 - Oct 3
Total with taxes and fees
1 Mi to Ferry: 'sea Street Cottage' in Hyannis
A beach with sand, flowers, and a clear sky.

4. Sal's Place

Sal's Place
2.0 star property
Hyannis
$590 nightly
The price is $658
Oct 1 - Oct 2
Total with taxes and fees
Sal's Place
A living room with teal walls, a brown leather sofa, a wooden coffee table, and a colorful rug.

5. Thompson House Cape Cod

Thompson House Cape Cod
3.0 star property
South Yarmouth
$965 nightly
The price is $1,105
Oct 10 - Oct 11
Total with taxes and fees
Thompson House Cape Cod
A hot tub with a tiled edge and a metal ladder, surrounded by a carpeted floor and wooden walls.

6. Brewster Green Resort

Brewster Green Resort
3.5 star property
Brewster
9.4 out of 10, Exceptional, (146 reviews)
"Very spacious rooms clean ,great location friendly staff,"
United States
Margaret
$199 nightly
The price is $228
Oct 1 - Oct 2
Total with taxes and fees
Brewster Green Resort
A living room with a leather sofa, a TV, a console table with decorative items, and a painting on the wall.

7. 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
$597 nightly
The price is $667
Oct 27 - Oct 28
Total with taxes and fees
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

Cape Sands Inn

Cape Sands Inn

10/10 Excellent
"Staff was excellent hotel clean"
Jerome 2-night trip
Posted 2 hours ago
Cape Sands Inn

Find out more about Osterville

Everything you need to know about Osterville vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Osterville vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. The list goes on, and on …and on.

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Osterville vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Osterville vacation rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Osterville. If you’re looking for a little peace, consider booking during the quieter low season months. For more hustle and bustle, you may prefer to visit Osterville in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $131 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Osterville rentals

At Expedia, we put the best Osterville vacation rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Osterville rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Osterville vacation.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Osterville. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

Explore a world of travel with Expedia

Frequently asked questions

Can I find vacation rentals in Osterville?

Yes, we give you a choice of vacation rentals in Osterville close to Stand Up & Paddle Cape Cod, or you can select a more remote option if you'd like a relaxing place to stay.

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

Stunning Oceanfront Home With Amazing Views ~ Private Beach! Ocean Beach Vista!: This vacation home rental outside of Osterville is located on the beach and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and an arcade game room.

How many vacation rentals are there in Osterville?

With 59 Expedia vacation rentals, you're sure 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 larger area.

What’s a vacation rental in Osterville like?

Vacation rentals are private properties you can book for a short or long stay in Osterville. Vacation rentals offer amenities such as patios, hot tubs, and fire pits so you'll have everything you need. If you're concerned about cleanliness, vacation rentals can provide a sense of privacy away from public hotel elevators and lobbies bustling with people while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great choice for a family trip.