Osterville Holiday Rentals

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Our top choices for Osterville holiday rentals

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, (3 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 NZ$673
includes taxes & fees
22 Feb - 23 Feb
WOW View! Waterfront Cottage. Private Beach, King Bed, Full Kitchen. Relax&Enjoy

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 NZ$1,124
includes taxes & fees
21 Feb - 22 Feb
Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!

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 NZ$479
includes taxes & fees
22 Feb - 23 Feb
Make this charming, modern retreat your home away from home!!

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 NZ$973
includes taxes & fees
21 Feb - 22 Feb
Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail

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 NZ$552
includes taxes & fees
23 Feb - 24 Feb
Cottage Oasis by Lake with Kayaks, Fire Pit & a Huge Yard

Big Sandy Beachcomber

Big Sandy Beachcomber
Ponds of Plymouth
9.6 out of 10, Exceptional, (13 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 NZ$641
includes taxes & fees
24 Feb - 25 Feb
Big Sandy Beachcomber

The Club at New Seabury

The Club at New Seabury
3.5 star property
New Seabury
9.0 out of 10, Wonderful, (352 reviews)
"Everything was superb, accommodations, check in service, check out service!!"
United States
Dianna
The price is NZ$314
includes taxes & fees
4 Mar - 5 Mar
The Club at New Seabury

Amazing Onset Getaway in the Starfish Suite

Amazing Onset Getaway in the Starfish Suite
Onset
9.6 out of 10, Exceptional, (25 reviews)
"The property was very nice and in a great location."
United States
Judith H.
The price is NZ$691
includes taxes & fees
23 Feb - 24 Feb
Amazing Onset Getaway in the Starfish Suite

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 NZ$838
includes taxes & fees
21 Feb - 22 Feb
Cozy Large Home in Harwich with Patio near Wequassett Resort

< 2 Mi to Beach: Cozy Cottage w/ Patio on Cape Cod

< 2 Mi to Beach: Cozy Cottage w/ Patio on Cape Cod
3.0 star property
Hyannis
< 2 Mi to Beach: Cozy Cottage w/ Patio on Cape Cod

The Nantucket Room Unit - #2

The Nantucket Room Unit - #2
Harwich port
9.8 out of 10, Exceptional, (51 reviews)
"amazing location and cute place to stay!"
United States
Adriana A.
The price is NZ$320
includes taxes & fees
22 Feb - 23 Feb
The Nantucket Room Unit - #2

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 NZ$625
includes taxes & fees
21 Feb - 22 Feb
Plymouth private ocean front oversized suite on the bluff of Cape Cod Bay

Spacious and Bright , Very Close to Beach!

Spacious and Bright , Very Close to Beach!
Onset
9.6 out of 10, Exceptional, (22 reviews)
"Amazing location, clean, spacious suite, great communication with the host, overall a great experience! "
United States
Bernadette C.
The price is NZ$631
includes taxes & fees
22 Feb - 23 Feb
Spacious and Bright , Very Close to Beach!

Quaint condo near private beach access with fireplace - close to dining

Quaint condo near private beach access with fireplace - close to dining
Dennis Port
9.0 out of 10, Wonderful, (63 reviews)
"Very nice location and the unit was clean and comfortable. "
United States
Jeanne M.
The price is NZ$615
includes taxes & fees
25 Feb - 26 Feb
Quaint condo near private beach access with fireplace - close to dining

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 NZ$893
includes taxes & fees
26 Feb - 27 Feb
Modern Beach & Pond Getaway; Heart of Cape Cod

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 NZ$1,315
includes taxes & fees
21 Feb - 22 Feb
Family Cottage Close to Beach!!

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)
"Wonderful stay, had everything we needed, Joy was very receptive to our messages. Thanks so much!"
United States
Alex K.
The price is NZ$332
includes taxes & fees
28 Feb - 1 Mar
Near Old Silver Beach Falmouth/Two bedroom , private bathroom and kitchenette

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 NZ$596
includes taxes & fees
22 Feb - 23 Feb
Ocean Edge Cape Cod 2 Bed 2 Bath, Golf & Free Resort Access - Brewster, MA

Falmouth Oasis

Falmouth Oasis
Falmouth
The price is NZ$811
includes taxes & fees
22 Feb - 23 Feb
Falmouth Oasis

Steps from Marina, beach, restaurants!

Steps from Marina, beach, restaurants!
Wareham
9.8 out of 10, Exceptional, (12 reviews)
"Beautiful space, wonderful location, amazing host. If I could give 100 stars I would! "
United States
Jaimie
The price is NZ$560
includes taxes & fees
23 Feb - 24 Feb
Steps from Marina, beach, restaurants!
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, 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 NZ$240 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?

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.