Osterville Vacation Rentals

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Our top choices for Osterville vacation rentals

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 CA $197
CA $499 total
includes taxes & fees
May 27 - May 28
1 Mi to Ferry: 'sea Street Cottage' in Hyannis

Sal's Place

Sal's Place
2.0 star property
Hyannis
The price is CA $1,012
CA $1,324 total
includes taxes & fees
May 21 - May 22
Sal's Place

The Club at New Seabury

The Club at New Seabury
3.5 star property
New Seabury
9.0 out of 10, Wonderful, (355 reviews)
"Our stay was great and Amy at the front desk is a god send she was absolutely the best."
United States
Jasmine
The Club at New Seabury

Brewster Green Resort

Brewster Green Resort
3.5 star property
Brewster
9.4 out of 10, Exceptional, (130 reviews)
"Mike is the best. Very clean environment and family welcome"
United States
Catherine
The price is CA $312
CA $357 total
includes taxes & fees
May 21 - May 22
Brewster Green Resort

The Cove at Yarmouth by Westgate Resorts

The Cove at Yarmouth by Westgate Resorts
3.0 star property
West Yarmouth
9.2 out of 10, Wonderful, (264 reviews)
"Clean rooms and pool. Great family resort."
United States
Julie
The price is CA $187
CA $214 total
includes taxes & fees
May 21 - May 22
The Cove at Yarmouth by Westgate Resorts

Coastal Haven in West Dennis -15

Coastal Haven in West Dennis -15
2.0 star property
West Dennis
The price is CA $468
CA $1,082 total
includes taxes & fees
May 22 - May 23
Coastal Haven in West Dennis -15

Wareham Cottage w/ Deck, Walk to Swift's Beach

Wareham Cottage w/ Deck, Walk to Swift's Beach
3.0 star property
Wareham
The price is CA $269
CA $747 total
includes taxes & fees
May 26 - May 27
Wareham Cottage w/ Deck, Walk to Swift's Beach

Walk to Beaches & Dining: Classic Cape Cod Cottage

Walk to Beaches & Dining: Classic Cape Cod Cottage
3.0 star property
Dennis Port
The price is CA $151
CA $601 total
includes taxes & fees
May 26 - May 27
Walk to Beaches & Dining: Classic Cape Cod Cottage

Bike to Beach: Centerville Home w/ Deck!

Bike to Beach: Centerville Home w/ Deck!
3.0 star property
Centerville
The price is CA $302
CA $870 total
includes taxes & fees
Jun 7 - Jun 8
Bike to Beach: Centerville Home w/ Deck!

Water Access 5-bed 2-bath Retreat

Water Access 5-bed 2-bath Retreat
2.0 star property
Hyannis
The price is CA $702
CA $1,456 total
includes taxes & fees
May 27 - May 28
Water Access 5-bed 2-bath Retreat
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.

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?

Steps to the Beach in East Falmouth, PET FRIENDLY & clubhouse heated pool. : This vacation home rental outside of Osterville is located near the beach and has a patio, a private yard, and a barbecue grill to put you at ease 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. You and your friends and family can relax into your vacation with amenities like a selection of books.

How many vacation rentals are there in Osterville?

With 69 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.