Osterville Holiday Rentals

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Holiday Rentals in Osterville

Holly Tree Resort

3.0 star property
9.0 out of 10, Wonderful, (355)
"Excellent place to stay, near great restaurants and shopping."
Holly Tree Resort

Edgewater Beach Resort, a VRI resort

3.5 star property
8.8 out of 10, Excellent, (286)
"All around a great place to stay!"
The price is AU$372
includes taxes & fees
23 Oct - 24 Oct
Edgewater Beach Resort, a VRI resort

Brewster Green Resort

3.5 star property
9.4 out of 10, Exceptional, (111)
"I only stayed for a night, but I found the property comfortable and quiet and I enjoyed the hot tub."
The price is AU$287
includes taxes & fees
2 Oct - 3 Oct
Brewster Green Resort

The Club at New Seabury

3.5 star property
9.0 out of 10, Wonderful, (334)
"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 "
The Club at New Seabury

Riverview Resort

3.0 star property
9.2 out of 10, Wonderful, (163)
"Overall everything was great. Rooms are clean. Very quiet. The upper outside deck requires repair but my understanding is owners association is aware and addressing. I think its our fourth time there. Keep going back. Only thing is we wished there was an outdoor pool. Would be great on those warm sunny days."
The price is AU$326
includes taxes & fees
22 Oct - 23 Oct
Riverview Resort

InnSeason Resorts Captain's Quarters

3.5 star property
9.8 out of 10, Exceptional, (181)
"Great location and helpful staff"
InnSeason Resorts Captain's Quarters

The Cove at Yarmouth by VRI Americas

3.5 star property
9.2 out of 10, Wonderful, (318)
"Clean, friendly staff and enjoyed the Loft Shack which is perfectly located adjacent to the outdoor pool. "
The Cove at Yarmouth by VRI Americas

Coastal chic meets French Provençal in this newly renovated oceanfront home.

10.0 out of 10, Exceptional, (85)
"Great stay! "
The price is AU$1,460
includes taxes & fees
30 Sept - 1 Oct
Coastal chic meets French Provençal in this newly renovated oceanfront home.

Sea Mist Resort

3.0 star property
8.6 out of 10, Excellent, (136)
"Great resort with suites, very cosy with great amenities, close to excellent beach and shopping."
The price is AU$345
includes taxes & fees
10 Oct - 11 Oct
Sea Mist Resort

Steps to the beach with an ocean view,

10.0 out of 10, Exceptional, (130)
"The house is a perfect place to stay. Close to the beach and the town of Hyannis. An ideal location for discovering the Cape Cod area. We felt relaxed and comfortable when we were there."
Steps to the beach with an ocean view,

Steps to the Ocean! Perfect Location!!!

10.0 out of 10, Exceptional, (225)
"Perfect for a couple and two kids"
Steps to the Ocean! Perfect Location!!!

*Oceanfront Beach Home*

10.0 out of 10, Exceptional, (82)
"Salt Eire was a lovely, cozy home. The beach views were phenomenal. The gas fireplace was perfect for a winter visit! The hosts supplied everything we could possibly need. It was a wonderful weekend getaway. "
*Oceanfront Beach Home*

Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs

6.4 out of 10, (30)
"The weather was perfect and our crew made the best of our trip."
Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs

Cape Cod Oceanfront Condo with Ocean View & Private Sandy Beach! [in Building A]

9.6 out of 10, Exceptional, (136)
"Great location by the beach. We loved staying here!"
The price is AU$929
includes taxes & fees
13 Oct - 14 Oct
Cape Cod Oceanfront Condo with Ocean View & Private Sandy Beach! [in Building A]

Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View

9.4 out of 10, Exceptional, (88)
"The location of this property cannot be beat! Our second time staying here."
The price is AU$858
includes taxes & fees
1 Oct - 2 Oct
Walking Distance From Oak Bluffs Ferry Terminal with 180 Degree Ocean View

Cape Cod Bay Home w/ Deck + Private Beach Access

9.6 out of 10, Exceptional, (33)
"I wanted to celebrate my daughter’s completion of her doctoral program with a dream vacation. My sister and two nieces joined us. The home was absolutely beautiful and the ocean view was amazing! We just couldn’t be more pleased with our stay! "
Cape Cod Bay Home w/ Deck + Private Beach Access

Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.

9.4 out of 10, Exceptional, (91)
"Close to buses, restaurants and ferries. 10/10, we would stay again."
The price is AU$770
includes taxes & fees
1 Oct - 2 Oct
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.

Oceanfront Escape house on SeaView Beach, Dog-Friendly!

9.8 out of 10, Exceptional, (121)
"We had a wonderful time on the Cape visiting with family from out of state. It was their first time on the Cape, and the location couldn't have been better! The host was kind and helpful. We would definitely stay here again. "
Oceanfront Escape house on SeaView Beach, Dog-Friendly!

Steps to a private beach in a classic Cape cottage. Pet-friendly!

8.8 out of 10, Excellent, (26)
"Quaint, quiet on the off season, great outdoor shower with plenty of hot water! Perfect beach getaway! "
Steps to a private beach in a classic Cape cottage. Pet-friendly!

Beach front, fenced yard, dogs welcome, central air, fire pit, 3 kayaks, hot tub

10.0 out of 10, Exceptional, (110)
"Great outdoor spaces. Loved the kayaks, beach and fire pit. Our 2 year old grandson loved the outdoor shower. Our dog had a ball chasing squirrels in the fenced backyard. We would definitely stay again. Close to everything in Falmouth including Woodneck beach, our low tide favorite. "
Beach front, fenced yard, dogs welcome, central air, fire pit, 3 kayaks, hot tub
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

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$287 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 patio, a garden and a BBQ 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 71 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.