Osterville Holiday Rentals

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Holiday Rentals in Osterville

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

2.0 star property
West Brewster
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 AU$1,045
includes taxes & fees
9 Dec - 10 Dec
Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!

Secluded-Entire 2nd floor Suite with Private Bath

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 AU$250
includes taxes & fees
29 Nov - 30 Nov
Secluded-Entire 2nd floor Suite with Private Bath

The Club at New Seabury

3.5 star property
Mashpee
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 AU$261
includes taxes & fees
25 Nov - 26 Nov
The Club at New Seabury

2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill

Dennis
10.0 out of 10, Exceptional, (176)
"Excellent property, super clean and location is perfect! "
United States
Karen B.
The price is AU$489
includes taxes & fees
1 Dec - 2 Dec
2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill

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

2.0 star property
Dennis
9.0 out of 10, Wonderful, (2)
"Very cute cottage. Very clean and grounds well manicured. "
United States
Anonymous traveller
The price is AU$533
includes taxes & fees
30 Nov - 1 Dec
Cottage Oasis by Lake with Kayaks, Fire Pit & a Huge Yard

Stylish 2nd floor Ocean Edge condo

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 AU$666
includes taxes & fees
25 Nov - 26 Nov
Stylish 2nd floor Ocean Edge condo

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

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 AU$658
includes taxes & fees
25 Nov - 26 Nov
The Seaview Suite: GREAT VIEWS, VERY CLOSE TO BEACH!

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

Wareham
9.6 out of 10, Exceptional, (5)
"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 AU$486
includes taxes & fees
30 Nov - 1 Dec
Make this charming, modern retreat your home away from home!!

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

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 AU$538
includes taxes & fees
1 Dec - 2 Dec
Ocean Edge Cape Cod 2 Bed 2 Bath, Golf & Free Resort Access - Brewster, MA

The Cove At Yarmouth

3.0 star property
West Yarmouth
9.2 out of 10, Wonderful, (243)
"Great place to stay. Clean, friendly and accommodating!"
United States
Mike
The price is AU$200
includes taxes & fees
25 Nov - 26 Nov
The Cove At Yarmouth

The SandDollar Suite - Private Deck with Gorgeous Views of Onset Beach

Onset
9.4 out of 10, Exceptional, (9)
"Great location"
United States
Robert C.
The price is AU$658
includes taxes & fees
30 Nov - 1 Dec
The SandDollar Suite - Private Deck with Gorgeous Views of Onset Beach

Oldest Town of Cape Cod In The Historic District

Sandwich
9.0 out of 10, Wonderful, (17)
"The house was a great cozy place to stay. Ed was pleasant and offer tips on where to go and what to see. We had a great time. "
United States
Justin V.
The price is AU$615
includes taxes & fees
25 Nov - 26 Nov
Oldest Town of Cape Cod In The Historic District

Steps from Marina, beach, restaurants!

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 AU$368
includes taxes & fees
25 Nov - 26 Nov
Steps from Marina, beach, restaurants!

Cozy Spacious Home Walk to the Beach & 1 Mile to Downtown Hyannis

Barnstable
8.6 out of 10, Excellent, (8)
"This was an amazing property and our host was awesome and checked in to make sure everything was going well. Would definitely stay here again! Thank you! "
United States
Kim
The price is AU$813
includes taxes & fees
30 Nov - 1 Dec
Cozy Spacious Home Walk to the Beach & 1 Mile to Downtown Hyannis

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

Dennis Port
9.0 out of 10, Wonderful, (62)
"Clean, beautiful, great location "
United States
Jennifer B.
The price is AU$449
includes taxes & fees
30 Nov - 1 Dec
Quaint condo near private beach access with fireplace - close to dining

The Nantucket Room Unit - #2

Harwich port
9.8 out of 10, Exceptional, (49)
"amazing location and cute place to stay!"
United States
Adriana A.
The price is AU$453
includes taxes & fees
25 Nov - 26 Nov
The Nantucket Room Unit - #2

Beach, Breeze & Bunk Beds. FamilyFun Steps to the Shore. Dog-Friendly, GameWall.

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.

Modern & Comfy Family Oasis ~ Games, Backyard, BBQ

Dennis
9.2 out of 10, Wonderful, (7)
"Five star because hosts were very responsive and truly went out of their way to make sure our stay was comfortable and enjoyable. Mid cape location is perfect for all the beaches we visit and biking we do. "
United States
Mark L.
The price is AU$880
includes taxes & fees
2 Dec - 3 Dec
Modern & Comfy Family Oasis ~ Games, Backyard, BBQ

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

West Brewster
9.6 out of 10, Exceptional, (50)
"House was perfect for our family reunion! "
United States
Gregg H.
The price is AU$811
includes taxes & fees
30 Nov - 1 Dec
Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail

Spacious and Bright , Very Close to Beach!

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 AU$658
includes taxes & fees
1 Dec - 2 Dec
Spacious and Bright , Very Close to Beach!
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 favourite 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 depend 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 AU$200 per night. Entering your travel dates in the search wizard might find you 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 68 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.