Osterville Vacation Rentals

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Our top choices for Osterville vacation rentals

Condo resort in New Seabury

The Club at New Seabury
3.5 star property
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.
$128 nightly
The price is $146
Dec 30 - Dec 31
Total with taxes and fees
The Club at New Seabury
7.4 out of 10, Good, (6)
"Cozy clean property that allows pets. Outdoor fire pit area was great and perfectly private. I also loved that the property had a private beach area with lounge chairs. I used the grill and had brunch on the patio table. So nice to enjoy the water from so many parts of the property. Area is quiet and a 7 min walk to Onset Center where you can grab icecream or on some weekdays there’s an even in town. Close to plazas for other needs."
United States
l E.
$501 nightly
The price is $519
Jan 4 - Jan 5, 2026
Total with taxes and fees
The Crab Cottage@The Compound Beach Resort Habitat

Aparthotel in Falmouth Heights

InnSeason Resorts Captain's Quarters
3.5 star property
9.8 out of 10, Exceptional, (192)
"Great property! Would definitely stay again."
United States
Brad
$134 nightly
The price is $153
Jan 1 - Jan 2, 2026
Total with taxes and fees
InnSeason Resorts Captain's Quarters
2.0 star property
$177 nightly
The price is $180
Jan 4 - Jan 5, 2026
Total with taxes and fees
The Bunk Room @ The Compound ~Fish-Hunt-Breakfast
9.8 out of 10, Exceptional, (11)
"Host was very responsive and the house provided everything we needed. Great location! "
United States
Ashley M.
$468 nightly
The price is $518
Jan 9 - Jan 10, 2026
Total with taxes and fees
Cozy Large Home in Harwich with Patio near Wequassett Resort
9.4 out of 10, Exceptional, (9)
"Great location"
United States
Robert C.
$345 nightly
The price is $385
Dec 26 - Dec 27
Total with taxes and fees
The SandDollar Suite - Private Deck with Gorgeous Views of Onset Beach
9.8 out of 10, Exceptional, (7)
"Great location, walk to beach. Close to restaurants and pirate's cove mini golf. Beds were comfy. In-house laundry was convenient. Great outdoor shower. "
United States
Amanda W.
$485 nightly
The price is $537
Dec 25 - Dec 26
Total with taxes and fees
Charming House by the Beach with Patio, Grill, FirePit
2.0 star property
9.0 out of 10, Wonderful, (2)
"Very cute cottage. Very clean and grounds well manicured. "
United States
Anonymous traveler
$316 nightly
The price is $350
Jan 5 - Jan 6, 2026
Total with taxes and fees
Cottage Oasis by Lake with Kayaks, Fire Pit & a Huge Yard
2.0 star property
10.0 out of 10, Exceptional, (25)
"Lovely house with nice location."
United States
amy d.
$628 nightly
The price is $719
Jan 16 - Jan 17, 2026
Total with taxes and fees
Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!

Aparthotel in Brewster

Brewster Green Resort
3.5 star property
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
$179 nightly
The price is $205
Dec 25 - Dec 26
Total with taxes and fees
Brewster Green Resort
9.6 out of 10, Exceptional, (177)
"Fenced in yard was perfect and close walk to both beach and restaurants."
United States
Mike Kayla B.
$306 nightly
The price is $350
Dec 26 - Dec 27
Total with taxes and fees
Dennisport : Dog Friendly with a fenced in large yard. 1/2 mile from beach
9.0 out of 10, Wonderful, (17)
"We really loved this place and I "
United States
Valerie D.
$356 nightly
The price is $407
Dec 25 - Dec 26
Total with taxes and fees
Oldest Town of Cape Cod In The Historic District
9.8 out of 10, Exceptional, (28)
"The space was perfect for our needs. The beds were comfortable, the rooms were very clean. If needed, we would definitely come back to this rental."
United States
Lynn
$345 nightly
The price is $385
Jan 1 - Jan 2, 2026
Total with taxes and fees
The Seaview Suite: GREAT VIEWS, VERY CLOSE TO BEACH!

Vacation Home in Ponds of Plymouth

Big Sandy Beachcomber
9.6 out of 10, Exceptional, (12)
"Our stay was perfect! The house was clean and the host very responsive throughout! Would definitely stay again!"
United States
Ben L.
$385 nightly
The price is $430
Jan 5 - Jan 6, 2026
Total with taxes and fees
Big Sandy Beachcomber
9.8 out of 10, Exceptional, (24)
"Location was unbelievable-right next to beach"
United States
Terry B.
$379 nightly
The price is $423
Dec 26 - Dec 27
Total with taxes and fees
Amazing Onset Getaway in the Starfish Suite
9.6 out of 10, Exceptional, (5)
"Great stay. Clean, comfortable, and exactly as listed. Perfect location with a great backyard to grill or sit by the fire pit. Check-in was easy and the host was very responsive. Would definitely book again!!"
United States
Laura D.
$276 nightly
The price is $308
Jan 1 - Jan 2, 2026
Total with taxes and fees
Make this charming, modern retreat your home away from home!!
9.8 out of 10, Exceptional, (178)
"Great location, clean property!"
United States
Lisa B.
$273 nightly
The price is $313
Dec 28 - Dec 29
Total with taxes and fees
2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill
8.0 out of 10, Very Good, (7)
"Love the place but felt like would of been better if the owner wasn’t around not that they where bad or annoying just didn’t feel like we was like away felt like we was being watched but besides that loved it Wish barbecue was working and speaker in house was weird set up but besides that it was amazing"
United States
Oscar B.
$650 nightly
The price is $691
Dec 28 - Dec 29
Total with taxes and fees
The Mermaid Cottage @ The Compound Beach Resort Habitat
10.0 out of 10, Exceptional, (5)
"Small cottage, but spacious vaulted ceilings and a great backyard hang out space with the hot tub. Close walk to public beach or parking nearby."
United States
Greg E.
$384 nightly
The price is $439
Jan 11 - Jan 12, 2026
Total with taxes and fees
Gold Anchor Cottage - private hot tub getaway!

Aparthotel in Mashpee

Sea Mist Resort
3.0 star property
8.6 out of 10, Excellent, (144)
"Just there for one night but very enjoyable stay."
United States
Shawna
$127 nightly
The price is $146
Dec 29 - Dec 30
Total with taxes and fees
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.
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Top Osterville Hotel Reviews

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 $146 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.

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?

Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs: This vacation home rental outside of Osterville is located in the city center and has a patio, a garden, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave.

How many vacation rentals are there in Osterville?

With 53 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.