Osterville Vacation Rentals

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Vacation Rentals in Osterville

The Club at New Seabury

3.5 star property
Mashpee
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

Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!

2.0 star property
West Brewster
10.0 out of 10, Exceptional, (24)
"The house was very clean and comfortable. The outdoor patio is especially nice as well."
United States
Gina C.
$543 nightly
The price is $622
Nov 20 - Nov 21
Total with taxes and fees
Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!

The Cove At Yarmouth

3.0 star property
West Yarmouth
9.2 out of 10, Wonderful, (243)
"Great place to stay. Clean, friendly and accommodating!"
United States
Mike
$113 nightly
The price is $130
Nov 23 - Nov 24
Total with taxes and fees
The Cove At Yarmouth

Cottage Oasis by Lake with Kayaks, Fire Pit & a Huge Yard

2.0 star property
Dennis
9.0 out of 10, Wonderful, (2)
"Very cute cottage. Very clean and grounds well manicured. "
United States
Anonymous traveler
$307 nightly
The price is $340
Dec 1 - Dec 2
Total with taxes and fees
Cottage Oasis by Lake with Kayaks, Fire Pit & a Huge Yard

Relaxed coastal cottage close to the beach with e-bikes, firepit, deck & AC

2.0 star property
Dennis Port
$460 nightly
The price is $527
Nov 23 - Nov 24
Total with taxes and fees
Relaxed coastal cottage close to the beach with e-bikes, firepit, deck & AC

Secluded-Entire 2nd floor Suite with Private Bath

Barnstable
10.0 out of 10, Exceptional, (1)
"Great, very close to downtown hyannis. Charming and a nice owner. "
United States
sam s.
$139 nightly
The price is $159
Nov 21 - Nov 22
Total with taxes and fees
Secluded-Entire 2nd floor Suite with Private Bath

Brewster Green Resort

3.5 star property
Brewster
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

Coastal Haven in West Dennis

2.0 star property
Dennis
10.0 out of 10, Exceptional, (3)
"Overall the property was perfect. Great location, super clean and plenty of room for our family of 4. The only negative I can say is that the property is a duplex and that’s not mentioned in the listing. Overall great spot and would stay there again!"
United States
Edward R.
$600 nightly
The price is $653
Nov 20 - Nov 21
Total with taxes and fees
Coastal Haven in West Dennis

Seaside Getaway - Harwichport Beachhouse

Harwich
9.8 out of 10, Exceptional, (9)
"Great location great property"
United States
Glenn M.
$422 nightly
The price is $483
Dec 2 - Dec 3
Total with taxes and fees
Seaside Getaway - Harwichport Beachhouse

Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail

West Brewster
9.6 out of 10, Exceptional, (50)
"Clean, lots of space, great location"
United States
Jenna M. B.
$461 nightly
The price is $528
Nov 30 - Dec 1
Total with taxes and fees
Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail

Beach, Breeze & Bunk Beds. FamilyFun Steps to the Shore. Dog-Friendly, GameWall.

Wareham
10.0 out of 10, Exceptional, (5)
"This property is just as described, even better in person. Very cute and clean, with everything you could possibly need during your stay. Great location and very quiet neighborhood. Definitely recommend. "
United States
Dayna F.
$391 nightly
The price is $437
Nov 21 - Nov 22
Total with taxes and fees
Beach, Breeze & Bunk Beds. FamilyFun Steps to the Shore. Dog-Friendly, GameWall.

The Seaview Suite: GREAT VIEWS, VERY CLOSE TO BEACH!

Onset
9.8 out of 10, Exceptional, (28)
"The space was perfect for our needs. The beds were comfortable, the rooms were very clean. If needed, we would definitely come back to this rental."
United States
Lynn
$376 nightly
The price is $420
Nov 20 - Nov 21
Total with taxes and fees
The Seaview Suite: GREAT VIEWS, VERY CLOSE TO BEACH!

Make this charming, modern retreat your home away from home!!

Wareham
9.6 out of 10, Exceptional, (5)
"Great stay. Clean, comfortable, and exactly as listed. Perfect location with a great backyard to grill or sit by the fire pit. Check-in was easy and the host was very responsive. Would definitely book again!!"
United States
Laura D.
$278 nightly
The price is $311
Nov 20 - Nov 21
Total with taxes and fees
Make this charming, modern retreat your home away from home!!

Dennis Port House: Beach, Hot Tub & Fire Pit Fun!

2.0 star property
Dennis
Dennis Port House: Beach, Hot Tub & Fire Pit Fun!

2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill

Dennis
10.0 out of 10, Exceptional, (176)
"Just got back from our stay in this house and we had an amazing time. The house was clean, check-in/check out instructions were clear. Perfect spot to stay for a Cape getaway! Will definitely stay there again."
United States
Heather O.
$273 nightly
The price is $313
Nov 22 - Nov 23
Total with taxes and fees
2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill

Cozy Spacious Home Walk to the Beach & 1 Mile to Downtown Hyannis

Barnstable
8.6 out of 10, Excellent, (8)
"This was an amazing property and our host was awesome and checked in to make sure everything was going well. Would definitely stay here again! Thank you! "
United States
Kim
$469 nightly
The price is $519
Nov 20 - Nov 21
Total with taxes and fees
Cozy Spacious Home Walk to the Beach & 1 Mile to Downtown Hyannis

Cozy Large Home in Harwich with Patio near Wequassett Resort

Harwich
9.8 out of 10, Exceptional, (11)
"We had a great time here - the kids’ room is truly special!"
Canada
Aravind
$471 nightly
The price is $522
Dec 7 - Dec 8
Total with taxes and fees
Cozy Large Home in Harwich with Patio near Wequassett Resort

Spacious and Bright , Very Close to Beach!

Onset
9.6 out of 10, Exceptional, (22)
"Amazing location, clean, spacious suite, great communication with the host, overall a great experience! "
United States
Bernadette C.
$376 nightly
The price is $420
Dec 1 - Dec 2
Total with taxes and fees
Spacious and Bright , Very Close to Beach!

Charming House by the Beach with Patio, Grill, FirePit

Bass River
9.8 out of 10, Exceptional, (7)
"What a tremendous location with a short 3 minute walk to Seaview Beach and a 5 minute walk to Skippers Clam House! The house has great sleeping capacity and has a great fire pit and outdoor seating area and a great outdoor shower with plenty of hot water for all! We will return in the future!"
United States
Neil M.
$509 nightly
The price is $564
Nov 23 - Nov 24
Total with taxes and fees
Charming House by the Beach with Patio, Grill, FirePit

Modern & Comfy Family Oasis ~ Games, Backyard, BBQ

Dennis
9.2 out of 10, Wonderful, (7)
"Five star because hosts were very responsive and truly went out of their way to make sure our stay was comfortable and enjoyable. Mid cape location is perfect for all the beaches we visit and biking we do. "
United States
Mark L.
$441 nightly
The price is $505
Nov 20 - Nov 21
Total with taxes and fees
Modern & Comfy Family Oasis ~ Games, Backyard, BBQ
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 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.

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.