Osterville Vacation Rentals

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Nov 19 - Nov 20
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Nov 20 - Nov 21
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Nov 21 - Nov 23
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Nov 28 - Nov 30

Vacation Rentals in Osterville

Front of property
Holly Tree Resort

Aparthotel in West Yarmouth

3.0 star property
9.0 out of 10, Wonderful, (367)
"We had a great stay!"
United States
Shelly
Holly Tree Resort
BBQ/picnic area
Edgewater Beach Resort, a VRI resort

Aparthotel in Dennis Port

3.5 star property
8.8 out of 10, Excellent, (291)
"Room was clean and the staff was great"
United States
Linda
Edgewater Beach Resort, a VRI resort
Private beach nearby, beach bar
The Club at New Seabury

Condo resort in Mashpee

3.5 star property
9.0 out of 10, Wonderful, (338)
"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 "
United States
Jose O.
$147 nightly
The price is $168
Nov 20 - Nov 21
Total with taxes and fees
The Club at New Seabury
Indoor pool, outdoor pool
Brewster Green Resort

Aparthotel in Brewster

3.5 star property
9.4 out of 10, Exceptional, (119)
"Super clean and a really large space! "
United States
Linda
$159 nightly
The price is $182
Nov 20 - Nov 21
Total with taxes and fees
Brewster Green Resort
5 bedrooms, desk, iron/ironing board, travel crib
Coastal chic meets French Provençal in this newly renovated oceanfront home.

Vacation Home in East Falmouth

10.0 out of 10, Exceptional, (88)
"Great stay! "
United States
Michael M.
$833 nightly
The price is $953
Dec 16 - Dec 17
Total with taxes and fees
Coastal chic meets French Provençal in this newly renovated oceanfront home.
Indoor pool, outdoor pool, sun loungers
Sea Mist Resort

Aparthotel in Mashpee

3.0 star property
8.6 out of 10, Excellent, (140)
"Just there for one night but very enjoyable stay."
United States
Shawna
Sea Mist Resort
Sundeck
Riverview Resort

Aparthotel in Bass River

3.0 star property
9.2 out of 10, Wonderful, (169)
"The room was big and very clean. The hotel is quaint and quiet. It does not have an elevator which could be an issue for some but we made it work. Overall a great place to stay. Very comfortable and inviting and we loved the amenities."
United States
Kathleen
Riverview Resort
On the beach, white sand
InnSeason Resorts Captain's Quarters

Aparthotel in Falmouth Heights

3.5 star property
9.8 out of 10, Exceptional, (192)
"Great property! Would definitely stay again."
United States
Brad
InnSeason Resorts Captain's Quarters
Aerial view
The Cove at Yarmouth by VRI Americas

Condo resort in West Yarmouth

3.5 star property
9.2 out of 10, Wonderful, (327)
"First time staying here and i was impressed"
United States
Wayne
The Cove at Yarmouth by VRI Americas
Outdoor dining
Newly Renovated Near Amazing Sunset Beach

Vacation Home in Falmouth

9.8 out of 10, Exceptional, (73)
"Great stay"
United States
Michael S.
Newly Renovated Near Amazing Sunset Beach
Beach nearby, sun loungers
Steps to the Ocean! Perfect Location!!!

Cottage in Barnstable

10.0 out of 10, Exceptional, (234)
"I absolutely loved my stay at this charming cottage in Hyannis! The place was cozy, spotless, and beautifully maintained. A perfect mix of comfort and Cape Cod charm. The location was great, close to the beach and local shops, yet quiet enough to relax and unwind."
United States
Maria
Steps to the Ocean! Perfect Location!!!
Seasonal outdoor pool
Beachside Village Resort

Apartment in Falmouth

3.0 star property
9.4 out of 10, Exceptional, (101)
"Very clean and quiet place to relax. Very friendly and professional! We will come back!"
United States
Emmanuelle Loriot
Beachside Village Resort
Exterior
Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs

Vacation Home in Oak Bluffs

6.4 out of 10, (31)
"indoor and outdoor comfortable space"
United States
Delores C.
Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs
Smart TV, fireplace, DVD player
Brand New Magnificent Oceanfront Home with Spectacular Views on Private Beach

Vacation Home in Sandwich

10.0 out of 10, Exceptional, (30)
"This was our second time at Second Chance and it was just as amazing as the first! George is a terrific host and the property and beach make for a perfect week!"
United States
Scott C.
Brand New Magnificent Oceanfront Home with Spectacular Views on Private Beach
On the beach, sun loungers
beachfront cottage at Chases Ocean Grove

Cottage in Dennis Port

9.6 out of 10, Exceptional, (33)
"Such a cool place! Just a few feet from the beach, we began and ended each day in the sand. The location is also great for traveling to all the cape cod hot spots. The cottage is really sweet and cozy— we hope to be back! "
United States
trisha d.
beachfront cottage at Chases Ocean Grove
Terrace/patio
Comfy Cape Home: Close to Mayflower Beach, golf course, and Downtown

Vacation Home in Dennis

10.0 out of 10, Exceptional, (16)
"Perfect location for Mayflower and Corporation beach , lovely house and yard for small family gatherings . "
United States
Nancy R.
$629 nightly
The price is $720
Nov 22 - Nov 23
Total with taxes and fees
Comfy Cape Home: Close to Mayflower Beach, golf course, and Downtown
Exterior
Beach front, fenced yard, dogs welcome, central air, fire pit, 3 kayaks, hot tub

Vacation Home in East Falmouth

10.0 out of 10, Exceptional, (112)
"The location and amenities were perfect. We are looking forward to returning next year."
United States
Trayce H.
Beach front, fenced yard, dogs welcome, central air, fire pit, 3 kayaks, hot tub
Interior
MOST CHIC SPOT! Your Martha's Vineyard Getaway!

Vacation Home in Oak Bluffs

10.0 out of 10, Exceptional, (7)
"Our kids and their friends had so much fun in the beautifully finished basement. Easy access to beach and ferry, would love to go back every year, the host was wonderful."
United States
Swathanthra M.
$1,053 nightly
The price is $1,176
Nov 20 - Nov 21
Total with taxes and fees
MOST CHIC SPOT! Your Martha's Vineyard Getaway!
On the beach, sun loungers, beach towels
*Oceanfront Beach Home*

Vacation Home in Sandwich

10.0 out of 10, Exceptional, (83)
"We had a great family vacation at the Oceanfront Beach Home. The location was perfect. Steps to the beautiful beach. The home had everything we needed for a family of nine. Everything you would need for a beach vacation was provided. I would highly recommend this home. "
United States
Michael R.
*Oceanfront Beach Home*
Interior
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.

Apartment in Oak Bluffs

9.4 out of 10, Exceptional, (91)
"Awesome view"
United States
Dave B.
$446 nightly
The price is $498
Nov 20 - Nov 21
Total with taxes and fees
Walking Distance From Oak Bluffs Ferry Terminal With 180 Degree Ocean View.
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

Sandwich Inn and Suites

Sandwich Inn and Suites

10/10 Excellent
"From the moment I stepped in the doorway to check in I felt comfortable and safe. I was greeted with a warm friendly smile and chec-in very efficient. This is the second time I have stayed here and it did not disappoint this time either. The checking area where you have breakfast is beautiful it's very well stocked and homie it is warm and inviting. The rooms are neat and spacious. And the grounds are gorgeous. I would not hesitate to recommend sandwich Inn and Suites to anybody and I will definitely take the opportunity to stay again gorgeous clspacious. The room is clean spacious the"
Kim 1-night trip
Posted 2 days ago
Sandwich Inn and Suites

Find out more about Osterville

Everything you need to know about Osterville vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Osterville vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Osterville vacation 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 low season months. For more hustle and bustle, you may prefer to visit Osterville in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $168 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Osterville rentals

At Expedia, we put the best Osterville vacation 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 vacation.

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 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?

Newly Renovated Near Amazing Sunset Beach: This vacation home rental outside of Osterville offers a patio, a garden, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. It has 5 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 games.

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.