A house by a lake with boats.

Osterville Holiday Rentals

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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
2 Mi to Dowses Beach! Couples Haven in Osterville

Peaceful Cottage in the Heart of Osterville Village Walk to Shops & Restaurants

Peaceful Cottage in the Heart of Osterville Village Walk to Shops & Restaurants
Barnstable
10.0 out of 10, Exceptional, (5 reviews)
"We had a great stay at the property, which was an ideal location - 5 minutes to the beach, playground, restaurants, etc. The fenced in yard made it very easy when having young children. The owner was very accommodating. I would recommended to future families. "
United States
Lauren G.
Peaceful Cottage in the Heart of Osterville Village Walk to Shops & Restaurants

3 Mi to Beaches: Peaceful Wareham Getaway

3 Mi to Beaches: Peaceful Wareham Getaway
3.0 star property
Wareham
The price is AU$365
includes taxes & fees
23 July - 24 July
3 Mi to Beaches: Peaceful Wareham Getaway

2-bedroom corporate apartment in delightful Plymouth with AC

2-bedroom corporate apartment in delightful Plymouth with AC
Plymouth
The price is AU$688
includes taxes & fees
21 July - 22 July
2-bedroom corporate apartment in delightful Plymouth with AC

Charming Antique Boathouse Located Directly On Long Pond.

Charming Antique Boathouse Located Directly On Long Pond.
Plymouth
9.8 out of 10, Exceptional, (116 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 AU$516
includes taxes & fees
22 July - 23 July
Charming Antique Boathouse Located Directly On Long Pond.

Beach Walks, Books & Bay Sunsets

Beach Walks, Books & Bay Sunsets
Brewster
The price is AU$1,456
includes taxes & fees
23 July - 24 July
Beach Walks, Books & Bay Sunsets

Walking distance to Private Beach! Charming Cottage North of Cape Cod.

Walking distance to Private Beach! Charming Cottage North of Cape Cod.
Wareham
9.6 out of 10, Exceptional, (14 reviews)
"Enjoyed the stay, would definitely come back!"
United States
Daniel W.
The price is AU$773
includes taxes & fees
10 Aug - 11 Aug
Walking distance to Private Beach! Charming Cottage North of Cape Cod.

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, (144 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 AU$535
includes taxes & fees
9 Aug - 10 Aug
Plymouth private ocean front oversized suite on the bluff of Cape Cod Bay

Oldest Town of Cape Cod In The Historic District

Oldest Town of Cape Cod In The Historic District
Sandwich
9.0 out of 10, Wonderful, (22 reviews)
"We enjoyed our two night stay."
United States
Lonnie W.
The price is AU$556
includes taxes & fees
28 July - 29 July
Oldest Town of Cape Cod In The Historic District

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)
"Great location & comfortable house for exploring Cape Cod & surrounding area"
United States
Linda
The price is AU$876
includes taxes & fees
20 July - 21 July
5 Mi to Beach: Cape Cod Getaway w/ Grill

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

The SandDollar Suite - Private Deck with Gorgeous Views of Onset Beach
Onset
9.6 out of 10, Exceptional, (11 reviews)
"Great location"
United States
Robert C.
The price is AU$824
includes taxes & fees
20 July - 21 July
The SandDollar Suite - Private Deck with Gorgeous Views of Onset Beach

1 Mi to Ferry: 'Sea Street Cottage' in Hyannis

1 Mi to Ferry: 'Sea Street Cottage' in Hyannis
Hyannis
8.8 out of 10, Excellent, (19 reviews)
"Perfect weekend getaway- super location. Cozy spot! Loved the area "
United States
Jill S.
The price is AU$525
includes taxes & fees
21 July - 22 July
1 Mi to Ferry: 'Sea Street Cottage' in Hyannis

Relaxing Cape Cod Cottage Getaway

Relaxing Cape Cod Cottage Getaway
Dennis
The price is AU$868
includes taxes & fees
4 Aug - 5 Aug
Relaxing Cape Cod Cottage Getaway

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, (25 reviews)
"Loved this property. "
United States
Carol S.
The price is AU$879
includes taxes & fees
11 Aug - 12 Aug
Adorable Cape Escape W/ Private Beach Access, Full Kitchen, & Perfect Location

Cape Cod Loft - Near Beaches & Canal

Cape Cod Loft - Near Beaches & Canal
Bourne
10.0 out of 10, Exceptional, (21 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 AU$457
includes taxes & fees
21 July - 22 July
Cape Cod Loft - Near Beaches & Canal

Private Cape Cod Cottage. Walk to Ellis Landing Beach!

Private Cape Cod Cottage. Walk to Ellis Landing Beach!
Brewster
10.0 out of 10, Exceptional, (43 reviews)
"Great location - privacy, comfy, and close to the beach!"
United States
Samantha K.
The price is AU$695
includes taxes & fees
21 July - 22 July
Private Cape Cod Cottage. Walk to Ellis Landing Beach!

Spacious and Bright , Very Close to Beach!

Spacious and Bright , Very Close to Beach!
Onset
9.8 out of 10, Exceptional, (26 reviews)
"Amazing location, clean, spacious suite, great communication with the host, overall a great experience! "
United States
Bernadette C.
The price is AU$793
includes taxes & fees
19 July - 20 July
Spacious and Bright , Very Close to Beach!

The Crab Cottage @ The Cape Cod Canal Compound LODGE

The Crab Cottage @ The Cape Cod Canal Compound LODGE
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 AU$1,974
includes taxes & fees
20 July - 21 July
The Crab Cottage @ The Cape Cod Canal Compound LODGE

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
9.8 out of 10, Exceptional, (116 reviews)
"perfect for couples, clean and pet friendly"
Canada
Jonathan
The price is AU$545
includes taxes & fees
10 Aug - 11 Aug
Stay in a TINY HOUSE!★0.4mi to Beach★Village★Restaurants★Pet Friendly ★ 2 bikes!

Charming West Yarmouth Cottage- Minutes to Beaches, Dining & Family Fun

Charming West Yarmouth Cottage- Minutes to Beaches, Dining & Family Fun
Yarmouth
10.0 out of 10, Exceptional, (2 reviews)
"Cute little cottage. Clean and pull out couch was very comfy! Great stay for a small group. Perfect location near a lot of very nice beaches. Would recommend Gray’s beach for sunset, parking is free!"
United States
Jessica Y.
The price is AU$815
includes taxes & fees
21 July - 22 July
Charming West Yarmouth Cottage- Minutes to Beaches, Dining & Family Fun
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$663 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?

Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs: This holiday home rental outside of Osterville is located in the city centre, and has a garden, a BBQ and air conditioning to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

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.