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Our top choices for Osterville holiday rentals

2 Mi to Dowses Beach! Couples Haven in Osterville

2 Mi to Dowses Beach! Couples Haven in Osterville
Osterville
The price is £258
includes taxes & fees
20 Jul - 21 Jul
2 Mi to Dowses Beach! Couples Haven in Osterville

3 Mi to Main Street: Newly Renovated Wareham Apt!

3 Mi to Main Street: Newly Renovated Wareham Apt!
3.0 star property
Wareham
The price is £192
includes taxes & fees
24 Jun - 25 Jun
3 Mi to Main Street: Newly Renovated Wareham Apt!

Ocean View Room @ Beach Resort / Habitat *HOT TUB*

Ocean View Room @ Beach Resort / Habitat *HOT TUB*
Cape Cod
The price is £232
includes taxes & fees
29 Jun - 30 Jun
Ocean View Room @ Beach Resort / Habitat *HOT TUB*

Walk to Swift's Beach! Classic Cottage w/ Deck

Walk to Swift's Beach! Classic Cottage w/ Deck
Wareham
9.8 out of 10, Exceptional, (6 reviews)
"The cottage was clean comfortable and quiet. We loved sitting out on the back deck. The beach was a short walk and very beautiful. We enjoyed our stay."
United States
Marylyn P.
The price is £416
includes taxes & fees
30 Jun - 1 Jul
Walk to Swift's Beach! Classic Cottage w/ Deck

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, (51 reviews)
"We loved the house. Simple and comfortable, exactly what we needed to relax. thank you."
United States
Michael M.
The price is £520
includes taxes & fees
29 Jun - 30 Jun
Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail

Charming studio in tranquil Falmouth with AC

Charming studio in tranquil Falmouth with AC
Falmouth
The price is £182
includes taxes & fees
29 Jun - 30 Jun
Charming studio in tranquil Falmouth with AC

The Crab Cottage@The Compound Beach Resort Habitat

The Crab Cottage@The Compound Beach Resort Habitat
Cape Cod
8.0 out of 10, Very good, (8 reviews)
"Cozy clean property that allows pets. Outdoor fire pit area was great and perfectly private. I also loved that the property had a private beach area with lounge chairs. I used the grill and had brunch on the patio table. So nice to enjoy the water from so many parts of the property. Area is quiet and a 7 min walk to Onset Center where you can grab icecream or on some weekdays there’s an even in town. Close to plazas for other needs."
United States
l E.
The price is £702
includes taxes & fees
30 Jun - 1 Jul
The Crab Cottage@The Compound Beach Resort Habitat

Dennis Beach House - Walk to Beach - Pet Friendly

Dennis Beach House - Walk to Beach - Pet Friendly
Dennis
8.0 out of 10, Very good, (10 reviews)
"Very cozy and quite neighborhood felt right at home."
United States
John S.
The price is £521
includes taxes & fees
25 Jun - 26 Jun
Dennis Beach House - Walk to Beach - Pet Friendly

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, (139 reviews)
"Adorable place with beautiful views tucked away in a quiet neighborhood. The hosts made us feel welcome and very accommodating. We didn’t want to leave! "
United States
Robine T.
The price is £289
includes taxes & fees
24 Jun - 25 Jun
Plymouth private ocean front oversized suite on the bluff of Cape Cod Bay

Stay in a TINY HOUSE!★0.4mi to Beach★Village★Restaurants★Pet Friendly ★ 2 bikes!

Stay in a TINY HOUSE!★0.4mi to Beach★Village★Restaurants★Pet Friendly ★ 2 bikes!
Dennis
9.6 out of 10, Exceptional, (116 reviews)
"perfect for couples, clean and pet friendly"
Canada
Jonathan
The price is £245
includes taxes & fees
25 Jun - 26 Jun
Stay in a TINY HOUSE!★0.4mi to Beach★Village★Restaurants★Pet Friendly ★ 2 bikes!

Ocean Edge Resort ground-floor condo with access to pools, hot tub, & tennis

Ocean Edge Resort ground-floor condo with access to pools, hot tub, & tennis
Brewster
9.0 out of 10, Wonderful, (20 reviews)
"Facility was excellent"
United States
Joe K.
The price is £416
includes taxes & fees
25 Jun - 26 Jun
Ocean Edge Resort ground-floor condo with access to pools, hot tub, & tennis

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 £274
includes taxes & fees
28 Jun - 29 Jun
1 Mi to Ferry: 'sea Street Cottage' in Hyannis

Adorable Cape Escape W/ Private Beach Access, Full Kitchen, & Perfect Location

Adorable Cape Escape W/ Private Beach Access, Full Kitchen, & Perfect Location
Dennis Port
9.0 out of 10, Wonderful, (24 reviews)
"Loved this property. "
United States
Carol S.
The price is £366
includes taxes & fees
25 Jun - 26 Jun
Adorable Cape Escape W/ Private Beach Access, Full Kitchen, & Perfect Location

Quaint & Clean Cape Cod Loft

Quaint & Clean Cape Cod Loft
Bourne
10.0 out of 10, Exceptional, (19 reviews)
"Really good place to stay close to Cape Cod and enjoy to visit the place ! Beautiful neighborhood and beautiful loft! Will come back for sure"
Canada
Olivier S.
The price is £238
includes taxes & fees
24 Jun - 25 Jun
Quaint & Clean Cape Cod Loft

5 Mi to Beach: Cape Cod Getaway w/ Grill

5 Mi to Beach: Cape Cod Getaway w/ Grill
Sandwich
9.6 out of 10, Exceptional, (37 reviews)
"Clean, quiet, and comfortable. Lots of towels, a basket of toiletries if you forgot something, and WiFi works great. Plenty of parking and nice back yard. Thank you for the enjoyable stay."
United States
Andrew S.
The price is £451
includes taxes & fees
28 Jun - 29 Jun
5 Mi to Beach: Cape Cod Getaway w/ Grill

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, (92 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 £469
includes taxes & fees
24 Jun - 25 Jun
Charming Beach Cottage, Steps To Beach; Ocean Views, Reasonably Priced

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, (66 reviews)
"Great location and very nice apartment"
United States
Phil M.
The price is £486
includes taxes & fees
6 Jul - 7 Jul
Quaint condo near private beach access with fireplace - close to dining

Mermaid House @ The Compound Beach Resort Habitat

Mermaid House @ The Compound Beach Resort Habitat
Cape Cod
8.4 out of 10, Very good, (8 reviews)
"Love the place but felt like would of been better if the owner wasn’t around not that they where bad or annoying just didn’t feel like we was like away felt like we was being watched but besides that loved it Wish barbecue was working and speaker in house was weird set up but besides that it was amazing"
United States
Oscar B.
The price is £593
includes taxes & fees
28 Jun - 29 Jun
Mermaid House @ The Compound Beach Resort Habitat

Spacious and Bright , Very Close to Beach!

Spacious and Bright , Very Close to Beach!
Onset
9.6 out of 10, Exceptional, (25 reviews)
"Amazing location, clean, spacious suite, great communication with the host, overall a great experience! "
United States
Bernadette C.
The price is £368
includes taxes & fees
24 Jun - 25 Jun
Spacious and Bright , Very Close to Beach!

2-bedroom corporate apartment in delightful Plymouth with AC

2-bedroom corporate apartment in delightful Plymouth with AC
Plymouth
The price is £328
includes taxes & fees
24 Jun - 25 Jun
2-bedroom corporate apartment in delightful Plymouth with AC
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 £274 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. 

Explore a world of travel with Expedia

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 61 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.