A house by a lake with boats.

Osterville Vacation Rentals

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Our top choices for Osterville vacation rentals

The Club at New Seabury

The Club at New Seabury
3.5 star property
New Seabury
9.0 out of 10, Wonderful, (362 reviews)
"The condo had everything we needed, and was clean, however there were a lot of ants on the main floor, mostly in the kitchen. This should definitely be looked into and maybe some traps set. There was a washer/dryer which was great and room service each day to change towels."
Canada
Rylea
The price is CA $715
CA $818 total
includes taxes & fees
Jul 15 - Jul 16
The Club at New Seabury

3 Mi to Beaches: Peaceful Wareham Getaway

3 Mi to Beaches: Peaceful Wareham Getaway
3.0 star property
Wareham
The price is CA $220
CA $361 total
includes taxes & fees
Jul 23 - Jul 24
3 Mi to Beaches: Peaceful Wareham Getaway

Water Access 5-bed 2-bath Retreat

Water Access 5-bed 2-bath Retreat
2.0 star property
Hyannis
The price is CA $790
CA $1,562 total
includes taxes & fees
Jul 12 - Jul 13
Water Access 5-bed 2-bath Retreat

5 Mi to Beach: Cape Cod Getaway w/ Grill

5 Mi to Beach: Cape Cod Getaway w/ Grill
3.0 star property
Sandwich
The price is CA $351
CA $849 total
includes taxes & fees
Jul 20 - Jul 21
5 Mi to Beach: Cape Cod Getaway w/ Grill

Coastal Haven in West Dennis -15

Coastal Haven in West Dennis -15
2.5 star property
West Dennis
The price is CA $526
CA $1,151 total
includes taxes & fees
Jul 12 - Jul 13
Coastal Haven in West Dennis -15

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

1 Mi to Ferry: 'sea Street Cottage' in Hyannis
3.0 star property
Hyannis
8.0 out of 10, Very good, (1 review)
"The cottage is in a great location close to Main Street and the harbor. Easy parking at the cottage and it’s in a walkable area. Decor is cute and nautical, but it does feel like the cottage is missing a few things. It sleeps 4, but there is not enough seating for 4 in the living room. An additional comfortable chair would be nice. A stackable washer and dryer would also be great, but there is very little space for anything- we even had trouble finding spots for our luggage. The fridge door...
United States
Christa
The price is CA $285
CA $564 total
includes taxes & fees
Jul 21 - Jul 22
1 Mi to Ferry: 'sea Street Cottage' in Hyannis

Pet-friendly Wareham Retreat Near Onset Beach!

Pet-friendly Wareham Retreat Near Onset Beach!
3.0 star property
Wareham
The price is CA $220
CA $361 total
includes taxes & fees
Jul 12 - Jul 13
Pet-friendly Wareham Retreat Near Onset Beach!

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

Walk to Swift's Beach! Classic Cottage w/ Deck
3.0 star property
Wareham
10.0 out of 10, Exceptional, (1 review)
"3 of us had a great time in Wareham. The cottage was exactly as advertised and close to many beaches"
United States
Tracy
The price is CA $473
CA $945 total
includes taxes & fees
Aug 8 - Aug 9
Walk to Swift's Beach! Classic Cottage w/ Deck

3 Mi to Onset Beach & Village! Pet-friendly Apt

3 Mi to Onset Beach & Village! Pet-friendly Apt
3.0 star property
Wareham
The price is CA $220
CA $361 total
includes taxes & fees
Jul 13 - Jul 14
3 Mi to Onset Beach & Village! Pet-friendly Apt

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 CA $220
CA $361 total
includes taxes & fees
Jul 23 - Jul 24
3 Mi to Main Street: Newly Renovated Wareham Apt!
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Osterville. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.

It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.

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Frequently asked questions

Can I find vacation rentals in Osterville?

Yes, we give you a choice of vacation rentals in Osterville close to Stand Up & Paddle Cape Cod, or you can select a more remote option if you'd like a relaxing place to stay.

What are some of the best vacation rentals that Osterville has to offer?

Cape Cod's "Beach Rose": This vacation home rental outside of Osterville offers a patio, a selection of games, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family.

How many vacation rentals are there in Osterville?

With 59 Expedia vacation rentals, you're sure 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 larger area.

What’s a vacation rental in Osterville like?

Vacation rentals are private properties you can book for a short or long stay in Osterville. Vacation rentals offer amenities such as patios, hot tubs, and fire pits so you'll have everything you need. If you're concerned about cleanliness, vacation rentals can provide a sense of privacy away from public hotel elevators and lobbies bustling with people while still allowing you the experience of travel. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a great choice for a family trip.