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Our top choices for Osterville holiday rentals

The Club at New Seabury

The Club at New Seabury
3.5 star property
New Seabury
9.0 out of 10, Wonderful, (355 reviews)
"Our stay was great and Amy at the front desk is a god send she was absolutely the best."
United States
Jasmine
The price is £196
includes taxes & fees
14 May - 15 May
The Club at New Seabury

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

1 Mi to Ferry: 'sea Street Cottage' in Hyannis
3.0 star property
Hyannis
The price is £268
includes taxes & fees
14 May - 15 May
1 Mi to Ferry: 'sea Street Cottage' in Hyannis

Plymouth private ocean front oversized suite on the bluff of Cape Cod Bay

Plymouth private ocean front oversized suite on the bluff of Cape Cod Bay
Plymouth
10.0 out of 10, Exceptional, (132 reviews)
"Beautiful room and view, hosts were communicative and check in/out were easy. Would definitely stay here again!"
United States
Alexander L.
The price is £282
includes taxes & fees
10 May - 11 May
Plymouth private ocean front oversized suite on the bluff of Cape Cod Bay

Brewster Green Resort

Brewster Green Resort
3.5 star property
Brewster
9.4 out of 10, Exceptional, (130 reviews)
"Mike is the best. Very clean environment and family welcome"
United States
Catherine
The price is £193
includes taxes & fees
21 May - 22 May
Brewster Green Resort

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, (263 reviews)
"Clean rooms and pool. Great family resort."
United States
Julie
The price is £118
includes taxes & fees
11 May - 12 May
The Cove at Yarmouth by Westgate Resorts

Charming Antique Boathouse Located Directly On Long Pond.

Charming Antique Boathouse Located Directly On Long Pond.
Plymouth
9.8 out of 10, Exceptional, (112 reviews)
"The hosts were very accommodating. Our arrival was late, and it was easy to get into the boathouse."
United States
Mark P.
The price is £268
includes taxes & fees
3 Jun - 4 Jun
Charming Antique Boathouse Located Directly On Long Pond.

The Seaview Suite: GREAT VIEWS, VERY CLOSE TO BEACH!

The Seaview Suite: GREAT VIEWS, VERY CLOSE TO BEACH!
Onset
9.8 out of 10, Exceptional, (28 reviews)
"The Seaview suite was great! Clean and nicely appointed. Great views from the deck. "
United States
Lauren M.
The price is £396
includes taxes & fees
9 May - 10 May
The Seaview Suite: GREAT VIEWS, VERY CLOSE TO BEACH!

Spacious and Bright , Very Close to Beach!

Spacious and Bright , Very Close to Beach!
Onset
9.6 out of 10, Exceptional, (23 reviews)
"Amazing location, clean, spacious suite, great communication with the host, overall a great experience! "
United States
Bernadette C.
The price is £396
includes taxes & fees
13 May - 14 May
Spacious and Bright , Very Close to Beach!

Coastal Haven in West Dennis -15

Coastal Haven in West Dennis -15
2.0 star property
West Dennis
The price is £577
includes taxes & fees
16 May - 17 May
Coastal Haven in West Dennis -15

Sweet Memories- Cozy 2 bedroom cottage in West Yarmouth

Sweet Memories- Cozy 2 bedroom cottage in West Yarmouth
Yarmouth
The price is £413
includes taxes & fees
31 May - 1 Jun
Sweet Memories- Cozy 2 bedroom cottage in West Yarmouth

Charming Beach Cottage, Steps To Beach; Ocean Views, Reasonably Priced

Charming Beach Cottage, Steps To Beach; Ocean Views, Reasonably Priced
New Seabury
8.6 out of 10, Excellent, (91 reviews)
"This was the perfect home for our weekend getaway! Joyce was wonderful to work with. Perfect location and beautiful home, just what we needed!"
United States
Courtney R.
The price is £459
includes taxes & fees
9 May - 10 May
Charming Beach Cottage, Steps To Beach; Ocean Views, Reasonably Priced

Wareham Cottage w/ Deck, Walk to Swift's Beach

Wareham Cottage w/ Deck, Walk to Swift's Beach
3.0 star property
Wareham
The price is £401
includes taxes & fees
17 May - 18 May
Wareham Cottage w/ Deck, Walk to Swift's Beach

New construction! Craigville Beach, Main St, Playground, Ice cream/restaurants!!

New construction! Craigville Beach, Main St, Playground, Ice cream/restaurants!!
Barnstable
10.0 out of 10, Exceptional, (31 reviews)
"It was a great stay and clean home. Recommend people to stay here"
United States
Charbel T.
The price is £913
includes taxes & fees
9 May - 10 May
New construction! Craigville Beach, Main St, Playground, Ice cream/restaurants!!

Family Cottage Close to Beach!!

Family Cottage Close to Beach!!
Harwichport
9.8 out of 10, Exceptional, (75 reviews)
"Everything was exactly as described - they provided beach towels and chairs which we used - the property was perfect for our stay"
United States
John N.
The price is £608
includes taxes & fees
9 May - 10 May
Family Cottage Close to Beach!!

Classic Cape House Walking Distance to the Beach - Many recent upgrades

Classic Cape House Walking Distance to the Beach - Many recent upgrades
Chatham
9.8 out of 10, Exceptional, (20 reviews)
"Mary was a wonderful host. The house was clean, close to beach and communication was wonderful! A great, relaxing stay!!"
United States
Kathleen T.
The price is £585
includes taxes & fees
10 May - 11 May
Classic Cape House Walking Distance to the Beach - Many recent upgrades

Modern Beach & Pond Getaway; Heart of Cape Cod

Modern Beach & Pond Getaway; Heart of Cape Cod
South Yarmouth
10.0 out of 10, Exceptional, (15 reviews)
"Great location and very comfortable rental home. Everything you need is included and the house is well stocked and clean!"
United States
Dennis S.
The price is £585
includes taxes & fees
10 May - 11 May
Modern Beach & Pond Getaway; Heart of Cape Cod

WOW View! Waterfront Cottage. Private Beach, King Bed, Full Kitchen. Relax&Enjoy

WOW View! Waterfront Cottage. Private Beach, King Bed, Full Kitchen. Relax&Enjoy
Sandwich
10.0 out of 10, Exceptional, (4 reviews)
"We really enjoyed our stay at this property. The view was amazing and had our own private beach to lounge at!"
United States
Sean H.
The price is £349
includes taxes & fees
4 Jun - 5 Jun
WOW View! Waterfront Cottage. Private Beach, King Bed, Full Kitchen. Relax&Enjoy

The Seashell Cove - Martha's Vineyard

The Seashell Cove - Martha's Vineyard
Katama
9.8 out of 10, Exceptional, (26 reviews)
"Nice and clean house, good location on the island, nice neighborhood "
United States
Eric C.
The price is £609
includes taxes & fees
10 May - 11 May
The Seashell Cove - Martha's Vineyard

MOST CHIC SPOT! Your Martha's Vineyard Getaway!

MOST CHIC SPOT! Your Martha's Vineyard Getaway!
Oak Bluffs
10.0 out of 10, Exceptional, (7 reviews)
"Our kids and their friends had so much fun in the beautifully finished basement. Easy access to beach and ferry, would love to go back every year, the host was wonderful."
United States
Swathanthra M.
The price is £891
includes taxes & fees
9 May - 10 May
MOST CHIC SPOT! Your Martha's Vineyard Getaway!

Beach Pass Included!

Beach Pass Included!
Barnstable
The price is £567
includes taxes & fees
9 May - 10 May
Beach Pass Included!
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 £118 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?

Eazy Breezy Beach Home: This holiday home rental outside of Osterville offers a fireplace, a patio and air conditioning to help you feel perfectly comfortable in your new surroundings. It has 4 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 69 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.