Osterville Holiday Rentals

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Check prices for these dates

In two weeks
29 May - 31 May
In two months
10 Jul - 12 Jul
In three months
7 Aug - 9 Aug
In four months
4 Sept - 6 Sept

Our top choices for Osterville holiday rentals

Private beach nearby, beach bar

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 HK$1,814
HK$2,076 total
includes taxes & fees
17 May - 18 May
The Club at New Seabury
Interior

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 HK$1,119
HK$2,843 total
includes taxes & fees
14 May - 15 May
1 Mi to Ferry: 'sea Street Cottage' in Hyannis
Terrace/patio

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 HK$1,957
HK$2,999 total
includes taxes & fees
13 May - 14 May
Plymouth private ocean front oversized suite on the bluff of Cape Cod Bay
Living area

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 HK$2,370
HK$2,712 total
includes taxes & fees
29 May - 30 May
Brewster Green Resort
Indoor pool, seasonal outdoor pool

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, (264 reviews)
"Clean rooms and pool. Great family resort."
United States
Julie
The price is HK$1,089
HK$1,247 total
includes taxes & fees
13 May - 14 May
The Cove at Yarmouth by Westgate Resorts
Exterior detail

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 HK$1,801
HK$2,851 total
includes taxes & fees
3 Jun - 4 Jun
Charming Antique Boathouse Located Directly On Long Pond.
Exterior

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)
"This place is beautiful, so clean and close to great restaurants and a clean and beautiful beach. We went to celebrate a birthday and it was perfect! "
United States
Larisa
The price is HK$2,107
HK$4,277 total
includes taxes & fees
13 May - 14 May
The Seaview Suite: GREAT VIEWS, VERY CLOSE TO BEACH!
Exterior

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 HK$2,107
HK$4,093 total
includes taxes & fees
13 May - 14 May
Spacious and Bright , Very Close to Beach!
3 bedrooms, desk

Coastal Haven in West Dennis -15

Coastal Haven in West Dennis -15
2.0 star property
West Dennis
The price is HK$2,573
HK$6,041 total
includes taxes & fees
13 May - 14 May
Coastal Haven in West Dennis -15
Exterior

Sweet Memories- Cozy 2 bedroom cottage in West Yarmouth

Sweet Memories- Cozy 2 bedroom cottage in West Yarmouth
Yarmouth
The price is HK$1,761
HK$3,880 total
includes taxes & fees
19 May - 20 May
Sweet Memories- Cozy 2 bedroom cottage in West Yarmouth
Property grounds

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 HK$2,349
HK$4,847 total
includes taxes & fees
13 May - 14 May
Charming Beach Cottage, Steps To Beach; Ocean Views, Reasonably Priced
Interior

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 HK$1,534
HK$4,254 total
includes taxes & fees
17 May - 18 May
Wareham Cottage w/ Deck, Walk to Swift's Beach
Fridge, microwave, oven, stovetop

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 HK$5,480
HK$9,703 total
includes taxes & fees
13 May - 14 May
New construction! Craigville Beach, Main St, Playground, Ice cream/restaurants!!
Exterior

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 HK$2,466
HK$6,397 total
includes taxes & fees
13 May - 14 May
Family Cottage Close to Beach!!
Smart TV, fireplace, books

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 HK$2,544
HK$6,182 total
includes taxes & fees
14 May - 15 May
Classic Cape House Walking Distance to the Beach - Many recent upgrades
Smart TV, fireplace, books

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 HK$2,713
HK$6,250 total
includes taxes & fees
18 May - 19 May
Modern Beach & Pond Getaway; Heart of Cape Cod
Interior

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 HK$1,683
HK$3,692 total
includes taxes & fees
4 Jun - 5 Jun
WOW View! Waterfront Cottage. Private Beach, King Bed, Full Kitchen. Relax&Enjoy
Smart TV, DVD player

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 HK$3,523
HK$6,498 total
includes taxes & fees
13 May - 14 May
The Seashell Cove - Martha's Vineyard
Interior

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 HK$4,306
HK$9,488 total
includes taxes & fees
15 May - 16 May
MOST CHIC SPOT! Your Martha's Vineyard Getaway!
Interior

Beach Pass Included!

Beach Pass Included!
Barnstable
The price is HK$4,613
HK$6,023 total
includes taxes & fees
13 May - 14 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

Cape Sands Inn

Cape Sands Inn

10/10 Excellent
"Fast check in Clean Amenities useful Friendly staff"
Brittney 1-night trip
Posted 2 hours ago
Cape Sands Inn

Find out more about Osterville

Search for holiday rentals in Osterville on Expedia! You can easily find your home rentals, villas, holiday apartments in Osterville using one of the methods below:

  • View our selection of featured holiday rentals in Osterville
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  • Enter your travel dates to view the best deals on holiday rentals in Osterville while they last

Look no further and take a look at our great range of rental properties in Osterville!

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.