Holiday Rentals in Osterville

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Holiday Rentals in Osterville

Condo resort in Mashpee

3.5 star property
9.0 out of 10, Wonderful, (338)
"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 price is €145
includes taxes & fees
1 Dec - 2 Dec
The Club at New Seabury

Condo in Dennis Port

9.0 out of 10, Wonderful, (62)
"Clean, beautiful, great location "
United States
Jennifer B.
The price is €251
includes taxes & fees
30 Nov - 1 Dec
Quaint condo near private beach access with fireplace - close to dining

Aparthotel in West Yarmouth

3.0 star property
9.2 out of 10, Wonderful, (243)
"Great place to stay. Clean, friendly and accommodating!"
United States
Mike
The price is €127
includes taxes & fees
30 Nov - 1 Dec
The Cove at Yarmouth by Westgate Resorts

Apartment in Wareham

9.8 out of 10, Exceptional, (12)
"Beautiful space, wonderful location, amazing host. If I could give 100 stars I would! "
United States
Jaimie
The price is €208
includes taxes & fees
1 Dec - 2 Dec
Steps from Marina, beach, restaurants!

Apartment in Barnstable

10.0 out of 10, Exceptional, (1)
"Great, very close to downtown hyannis. Charming and a nice owner. "
United States
sam s.
The price is €141
includes taxes & fees
2 Dec - 3 Dec
Secluded-Entire 2nd floor Suite with Private Bath

Holiday Home in Dennis

10.0 out of 10, Exceptional, (176)
"Excellent property, super clean and location is perfect! "
United States
Karen B.
The price is €276
includes taxes & fees
3 Dec - 4 Dec
2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill

Holiday Home in Dennis

10.0 out of 10, Exceptional, (2)
"A great place! Cute and clean with all the comforts of home...and more!"
United States
Kristen D.
The price is €289
includes taxes & fees
28 Dec - 29 Dec
Eazy Breezy Beach Home

Holiday Home in West Brewster

2.0 star property
10.0 out of 10, Exceptional, (24)
"Beautiful, well appointed home ideally situated for exploring all the Cape has to offer from the Canal to Provincetown. Very enjoyable and relaxing vacation venue."
United States
Art T.
The price is €590
includes taxes & fees
9 Dec - 10 Dec
Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!

Holiday Home in Dennis

2.0 star property
9.0 out of 10, Wonderful, (2)
"Very cute cottage. Very clean and grounds well manicured. "
United States
Anonymous traveller
The price is €298
includes taxes & fees
30 Nov - 1 Dec
Cottage Oasis by Lake with Kayaks, Fire Pit & a Huge Yard

Condo in Harwich port

9.8 out of 10, Exceptional, (49)
"amazing location and cute place to stay!"
United States
Adriana A.
The price is €258
includes taxes & fees
30 Nov - 1 Dec
The Nantucket Room Unit - #2

Apartment in Onset

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
The price is €372
includes taxes & fees
30 Nov - 1 Dec
The Seaview Suite: GREAT VIEWS, VERY CLOSE TO BEACH!

Apartment in Brewster

9.8 out of 10, Exceptional, (9)
"Great property. It looks like it was recently renovated and done really well. Convenient to the beaches and restaurants, and golf. We love Brewster. "
United States
Garret J.
The price is €376
includes taxes & fees
30 Nov - 1 Dec
Stylish 2nd floor Ocean Edge condo

Holiday Home in Wareham

10.0 out of 10, Exceptional, (5)
"This property is just as described, even better in person. Very cute and clean, with everything you could possibly need during your stay. Great location and very quiet neighborhood. Definitely recommend. "
United States
Dayna F.
Beach, Breeze & Bunk Beds. FamilyFun Steps to the Shore. Dog-Friendly, GameWall.

Holiday Home in Plymouth

10.0 out of 10, Exceptional, (129)
"Numerous options of comfortable seating to enjoy great open ocean view. "
United States
Jen
The price is €337
includes taxes & fees
30 Nov - 1 Dec
Plymouth private ocean front oversized suite on the bluff of Cape Cod Bay

Holiday Home in Bass River

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.
The price is €537
includes taxes & fees
1 Dec - 2 Dec
Charming House by the Beach with Patio, Grill, FirePit

Holiday Home in West Brewster

9.6 out of 10, Exceptional, (50)
"House was perfect for our family reunion! "
United States
Gregg H.
The price is €457
includes taxes & fees
30 Nov - 1 Dec
Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail

Holiday Home in Ponds of Plymouth

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.
The price is €346
includes taxes & fees
1 Dec - 2 Dec
Big Sandy Beachcomber

Apartment in Onset

9.6 out of 10, Exceptional, (22)
"Amazing location, clean, spacious suite, great communication with the host, overall a great experience! "
United States
Bernadette C.
The price is €371
includes taxes & fees
1 Dec - 2 Dec
Spacious and Bright , Very Close to Beach!

Holiday Home in Dennis

10.0 out of 10, Exceptional, (16)
"Perfect location for Mayflower and Corporation beach , lovely house and yard for small family gatherings . "
United States
Nancy R.
The price is €636
includes taxes & fees
7 Dec - 8 Dec
Comfy Cape Home: Close to Mayflower Beach, golf course, and Downtown

Condo in Brewster

10.0 out of 10, Exceptional, (41)
"My son was playing in Massachusetts Open Golf Tournament- location and property were perfect. - definitely visit again. "
United States
Sal S.
The price is €303
includes taxes & fees
1 Dec - 2 Dec
Ocean Edge Cape Cod 2 Bed 2 Bath, Golf & Free Resort Access - Brewster, MA
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 holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Osterville holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Osterville holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Osterville holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Osterville holiday rentals we have selected for you start as low as €145 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Osterville rentals

At Expedia, we put the best Osterville holiday 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 holiday.

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 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?

Newly Renovated Near Amazing Sunset Beach: This holiday home rental outside of Osterville offers a patio, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games.

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.