Osterville Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
20 Mar - 22 Mar
In two months
1 May - 3 May
In three months
29 May - 31 May
In four months
26 Jun - 28 Jun

Our top choices for Osterville holiday rentals

Sun-loungers, beach towels

Make this charming, modern retreat your home away from home!!

Make this charming, modern retreat your home away from home!!
Wareham
9.8 out of 10, Exceptional, (6 reviews)
"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.
The price is HK$1,049
HK$2,290 total
includes taxes & fees
3 Mar - 4 Mar
Make this charming, modern retreat your home away from home!!
Smart TV, books

Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!

Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!
West Brewster
10.0 out of 10, Exceptional, (25 reviews)
"Lovely house with nice location."
United States
amy d.
The price is HK$997
HK$5,395 total
includes taxes & fees
4 Mar - 5 Mar
Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!
Property grounds

Cottage Oasis by Lake with Kayaks, Fire Pit & a Huge Yard

Cottage Oasis by Lake with Kayaks, Fire Pit & a Huge Yard
Dennis
8.8 out of 10, Excellent, (3 reviews)
"Very cute cottage. Very clean and grounds well manicured. "
United States
Anonymous traveller
The price is HK$931
HK$2,434 total
includes taxes & fees
3 Mar - 4 Mar
Cottage Oasis by Lake with Kayaks, Fire Pit & a Huge Yard
Dining

Big Sandy Beachcomber

Big Sandy Beachcomber
Ponds of Plymouth
9.6 out of 10, Exceptional, (14 reviews)
"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 HK$1,039
HK$3,074 total
includes taxes & fees
3 Mar - 4 Mar
Big Sandy Beachcomber
Outdoor dining

Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail

Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail
West Brewster
9.6 out of 10, Exceptional, (50 reviews)
"House was perfect for our family reunion! "
United States
Gregg H.
The price is HK$1,033
HK$4,616 total
includes taxes & fees
3 Mar - 4 Mar
Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail
Pool

Cozy Large Home in Harwich with Patio near Wequassett Resort

Cozy Large Home in Harwich with Patio near Wequassett Resort
Harwich
9.8 out of 10, Exceptional, (11 reviews)
"Host was very responsive and the house provided everything we needed. Great location! "
United States
Ashley M.
The price is HK$1,174
HK$3,977 total
includes taxes & fees
8 Mar - 9 Mar
Cozy Large Home in Harwich with Patio near Wequassett Resort
Interior

Near Old Silver Beach Falmouth/Two bedroom , private bathroom and kitchenette

Near Old Silver Beach Falmouth/Two bedroom , private bathroom and kitchenette
Falmouth
8.2 out of 10, Very good, (24 reviews)
"My husband and I had a great weekend stay! The location was perfect. We walked to a coffee shop for breakfast and then took our bikes down the beautiful Shining Sea Trail to Woods Hole for the day. We did not need to drive at all. Listing was accurate, and check in was easy. Shared bathroom was well managed. The hosts were very kind and made sure we had everything we needed."
United States
Elizabeth V.
The price is HK$1,400
HK$2,382 total
includes taxes & fees
6 Mar - 7 Mar
Near Old Silver Beach Falmouth/Two bedroom , private bathroom and kitchenette
Smart TV, fireplace

Coastal Haven in West Dennis

Coastal Haven in West Dennis
Dennis
10.0 out of 10, Exceptional, (3 reviews)
"Overall the property was perfect. Great location, super clean and plenty of room for our family of 4. The only negative I can say is that the property is a duplex and that’s not mentioned in the listing. Overall great spot and would stay there again!"
United States
Edward R.
The price is HK$1,873
HK$4,604 total
includes taxes & fees
3 Mar - 4 Mar
Coastal Haven in West Dennis
Fridge, microwave, oven, stovetop

Cozy Riverfront Stay in Wareham

Cozy Riverfront Stay in Wareham
Wareham
10.0 out of 10, Exceptional, (3 reviews)
"Perfect for wedding guests. Spacious, clean and great viewWould definitely stay again"
United States
Karleen L.
The price is HK$1,027
HK$3,008 total
includes taxes & fees
3 Mar - 4 Mar
Cozy Riverfront Stay in Wareham
Exterior

Spacious and Bright , Very Close to Beach!

Spacious and Bright , Very Close to Beach!
Onset
9.6 out of 10, Exceptional, (22 reviews)
"This is a really lovely spot, spacious common area (kitchen & living room), and nice bedrooms with comfortable beds, and a fabulous location across from the beach. We were in town for a wedding & rented two units in the building for extended family, which worked out really well. Everything was as pictured; note is that one bedroom is only accessed through the bathroom or another bedroom, but that was not a problem for us. The host was easy to communicate with and very responsive to questions...
United States
Alice S.
The price is HK$1,120
HK$2,990 total
includes taxes & fees
8 Mar - 9 Mar
Spacious and Bright , Very Close to Beach!
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)
"Property needs a refresh."
United States
Paul B.
The price is HK$2,347
HK$4,862 total
includes taxes & fees
3 Mar - 4 Mar
Charming Beach Cottage, Steps To Beach; Ocean Views, Reasonably Priced
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, (129 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$1,956
HK$2,997 total
includes taxes & fees
3 Mar - 4 Mar
Plymouth private ocean front oversized suite on the bluff of Cape Cod Bay
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, (12 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$1,296
HK$4,276 total
includes taxes & fees
12 Mar - 13 Mar
Modern Beach & Pond Getaway; Heart of Cape Cod
Beach nearby

Ocean Edge Cape Cod 2 Bed 2 Bath, Golf & Free Resort Access - Brewster, MA

Ocean Edge Cape Cod 2 Bed 2 Bath, Golf & Free Resort Access - Brewster, MA
Brewster
10.0 out of 10, Exceptional, (42 reviews)
"Great place!"
United States
Michael P.
The price is HK$1,753
HK$3,036 total
includes taxes & fees
3 Mar - 4 Mar
Ocean Edge Cape Cod 2 Bed 2 Bath, Golf & Free Resort Access - Brewster, MA
Interior

Gorgeous Home 1 mile to Beach, by Cape Cod Bikepath

Gorgeous Home 1 mile to Beach, by Cape Cod Bikepath
Dennis
The price is HK$1,557
HK$4,315 total
includes taxes & fees
6 Mar - 7 Mar
Gorgeous Home 1 mile to Beach, by Cape Cod Bikepath
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$2,464
HK$6,393 total
includes taxes & fees
3 Mar - 4 Mar
Family Cottage Close to Beach!!
Outdoor dining

The Secret Hide-Out Waterfront Cottage w/ Kayaks and Fire Pit

The Secret Hide-Out Waterfront Cottage w/ Kayaks and Fire Pit
Wareham
The price is HK$2,077
HK$3,849 total
includes taxes & fees
4 Mar - 5 Mar
The Secret Hide-Out Waterfront Cottage w/ Kayaks and Fire Pit
Interior

Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
Falmouth
10.0 out of 10, Exceptional, (212 reviews)
"This beautiful well-appointed home was the perfect spot for a girlfriend’s getaway. Walkable to the shops and restaurants, nice big rooms for chats, and a great kitchen island to congregate around for breakfast. We loved our time here!"
United States
Annemarie G.
The price is HK$923
HK$3,429 total
includes taxes & fees
3 Mar - 4 Mar
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
Outdoor dining

Cape Cod Villa pond front vacation home, retreat, spa, venue, film location

Cape Cod Villa pond front vacation home, retreat, spa, venue, film location
Harwich - Brewster Border
10.0 out of 10, Exceptional, (6 reviews)
"Lovely property with attentive hosts "
United States
marian t.
The price is HK$5,070
HK$9,464 total
includes taxes & fees
3 Mar - 4 Mar
Cape Cod Villa pond front vacation home, retreat, spa, venue, film location
Interior

Eazy Breezy Beach Home

Eazy Breezy Beach Home
Dennis
8.0 out of 10, Very good, (5 reviews)
"A great place! Cute and clean with all the comforts of home...and more!"
United States
Kristen D.
The price is HK$1,619
HK$2,606 total
includes taxes & fees
3 Mar - 4 Mar
Eazy Breezy Beach Home
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

Iris Hotel Cape Cod

Iris Hotel Cape Cod

10/10 Excellent
"The room was clean, comfortable, nice, and the staff very helpful, friendly, and most accommodating ! The breakfast muffins were outstanding ! "
Lewis 2-night trip
Posted 3 days ago
Iris Hotel Cape Cod

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
  • Use the map to find apartments and other holiday homes in the Osterville neighbourhood you prefer
  • 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?

Coastal chic meets French Provençal in this newly renovated oceanfront home. : This holiday home rental outside of Osterville is located on the beach, and has a fireplace, a balcony and a BBQ to put you at ease 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 can relax into your holiday with a garden and a selection of games.

How many holiday rentals are there in Osterville?

With 63 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.