A house by a lake with boats.

Osterville Vacation Rentals

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Our top choices for Osterville vacation rentals

1. Beach pass included • Modern 3BR Osterville retreat, walkable to village center

Beach pass included • Modern 3BR Osterville retreat, walkable to village center
Osterville
10.0 out of 10, Exceptional, (20 reviews)
"Very comfortable, close to town, all around great stay."
United States
Elizabeth C.
The price is CA $660
CA $1,364 total
includes taxes & fees
Sep 20 - Sep 21
Beach pass included • Modern 3BR Osterville retreat, walkable to village center

2. The Club at New Seabury

The Club at New Seabury
3.5 star property
New Seabury
9.0 out of 10, Wonderful, (367 reviews)
"Overall, very good. Pool and beach area were not the most convenient to access. Short drive required."
United States
Grayson
The price is CA $281
CA $322 total
includes taxes & fees
Sep 7 - Sep 8
The Club at New Seabury

3. Serene Haven w/ No Shared Spaces | Cape Cod

Serene Haven w/ No Shared Spaces | Cape Cod
Marston Mills
10.0 out of 10, Exceptional, (19 reviews)
"Marston Hills is a great location for getting to many great areas of Cape Cod. The house was very clean and nicely furnished. "
United States
Dana S.
The price is CA $313
CA $517 total
includes taxes & fees
Aug 31 - Sep 1
Serene Haven w/ No Shared Spaces | Cape Cod

4. 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, (268 reviews)
"P Indoor pool and hot tub loved and the outdoor Shack was great"
United States
BELKIS
The price is CA $206
CA $235 total
includes taxes & fees
Sep 28 - Sep 29
The Cove at Yarmouth by Westgate Resorts

5. New Seabury Cape Condo + Pool & Beach Escape

New Seabury Cape Condo + Pool & Beach Escape
New Seabury
10.0 out of 10, Exceptional, (87 reviews)
"Great condo, great location. Fully equipped kitchen and awesome patio. "
United States
Jeff V.
The price is CA $136
CA $468 total
includes taxes & fees
Sep 2 - Sep 3
New Seabury Cape Condo + Pool & Beach Escape

6. Newly Renovated Hyannis Home w/ Fire Pit & Yard

Newly Renovated Hyannis Home w/ Fire Pit & Yard
Hyannis
10.0 out of 10, Exceptional, (7 reviews)
"Really enjoyed our stay. Very clean and comfortable home. The communication with the owners was excellent. We would definitely visit again. "
United States
Shawn B.
The price is CA $236
CA $796 total
includes taxes & fees
Aug 31 - Sep 1
Newly Renovated Hyannis Home w/ Fire Pit & Yard

7. WOW View! Waterfront Cottage. Private Beach, King Bed, Full Kitchen. Relax&Enjoy

WOW View! Waterfront Cottage. Private Beach, King Bed, Full Kitchen. Relax&Enjoy
Sandwich
10.0 out of 10, Exceptional, (4 reviews)
"We really enjoyed our stay at this property. The view was amazing and had our own private beach to lounge at!"
United States
Sean H.
The price is CA $341
CA $716 total
includes taxes & fees
Aug 31 - Sep 1
WOW View! Waterfront Cottage. Private Beach, King Bed, Full Kitchen. Relax&Enjoy

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

Cozy Spacious Home Walk to the Beach & 1 Mile to Downtown Hyannis
Barnstable
8.8 out of 10, Excellent, (9 reviews)
"Nice location, quiet neighborhood, comfortable, and clean with a feeling of newness. Nice time of year to enjoy the porch and there was plenty of room for our group of seven. Three couches in the basement! Easy to get to town or beaches, etc. Host was helpful and communicative."
United States
Jen M.
The price is CA $235
CA $746 total
includes taxes & fees
Sep 28 - Sep 29
Cozy Spacious Home Walk to the Beach & 1 Mile to Downtown Hyannis

9. Sunny Cape Home, Bike to Beach, Central AC

Sunny Cape Home, Bike to Beach, Central AC
Barnstable
The price is CA $765
CA $1,001 total
includes taxes & fees
Sep 23 - Sep 24
Sunny Cape Home, Bike to Beach, Central AC

10. Waterfront with Kayaks • Amazing Views • Pets • Walk to Craigville Beach

Waterfront with Kayaks • Amazing Views • Pets • Walk to Craigville Beach
Centerville
9.6 out of 10, Exceptional, (54 reviews)
"Excellent location for our needs and good functionality of the house itself also for our needs. Nice landscaping and secure backyard that was very pretty."
United States
Nancy J.
The price is CA $875
CA $1,544 total
includes taxes & fees
Sep 7 - Sep 8
Waterfront with Kayaks • Amazing Views • Pets • Walk to Craigville Beach

11. Holly Tree Resort

Holly Tree Resort
3.0 star property
West Yarmouth
9.2 out of 10, Wonderful, (412 reviews)
"Check in was easy, rooms clean, easy location."
United States
William S
The price is CA $328
CA $376 total
includes taxes & fees
Aug 31 - Sep 1
Holly Tree Resort

12. New construction! Craigville Beach, Main St, Playground, Ice cream/restaurants!!

New construction! Craigville Beach, Main St, Playground, Ice cream/restaurants!!
Barnstable
10.0 out of 10, Exceptional, (38 reviews)
"It was a great stay and clean home. Recommend people to stay here"
United States
Charbel T.
The price is CA $1,112
CA $1,910 total
includes taxes & fees
Aug 31 - Sep 1
New construction! Craigville Beach, Main St, Playground, Ice cream/restaurants!!

13. Hyannis Hideaway in Cape Cod

Hyannis Hideaway in Cape Cod
Barnstable
9.6 out of 10, Exceptional, (10 reviews)
"Awesome private property, close to Main Street and Craigsville beach. My friends and I stay in Hyannis every 4th of July and this home was super accommodating for groups and close to everything. Great stay would recommend. "
United States
Hunter W.
The price is CA $605
CA $1,103 total
includes taxes & fees
Sep 28 - Sep 29
Hyannis Hideaway in Cape Cod

14. SANDTRAP! BEACH short walk! Marinas, Golf, Shopping & Restaurants short drive!

SANDTRAP! BEACH short walk! Marinas, Golf, Shopping & Restaurants short drive!
Yarmouth
10.0 out of 10, Exceptional, (64 reviews)
"Loved the house. Had everything we needed and more!"
United States
Erica H.
The price is CA $343
CA $716 total
includes taxes & fees
Sep 8 - Sep 9
SANDTRAP! BEACH short walk! Marinas, Golf, Shopping & Restaurants short drive!

15. Beach Lovers Escape

Beach Lovers Escape
Yarmouth
10.0 out of 10, Exceptional, (49 reviews)
"Just as advertised, lots of room for guests and great backyard area. Would definitely stay again."
United States
alex f.
The price is CA $393
CA $1,105 total
includes taxes & fees
Sep 8 - Sep 9
Beach Lovers Escape

16. Cozy Cottage walk to Menauhant Beach

Cozy Cottage walk to Menauhant Beach
East Falmouth
8.8 out of 10, Excellent, (8 reviews)
"It was a great weekend spot. Had everything we needed, nicely decorated, and in a great and private location"
United States
Grace P.
The price is CA $266
CA $1,046 total
includes taxes & fees
Sep 8 - Sep 9
Cozy Cottage walk to Menauhant Beach

17. Cozy One Bedroom Cabin on Cape Cod Campground!

Cozy One Bedroom Cabin on Cape Cod Campground!
Bass River
9.0 out of 10, Wonderful, (46 reviews)
"Great stay, great communication, highly recommend "
United States
Rick F.
The price is CA $306
CA $474 total
includes taxes & fees
Sep 8 - Sep 9
Cozy One Bedroom Cabin on Cape Cod Campground!

18. Adorable beach house! 3 min walk to beach!

Adorable beach house! 3 min walk to beach!
Popponesset
9.8 out of 10, Exceptional, (30 reviews)
"We had a great stay! The place was clean, well decorated, and close to the beach! The property managers were also very nice and easy to reach out to!"
United States
Allison W.
The price is CA $904
CA $1,636 total
includes taxes & fees
Sep 20 - Sep 21
Adorable beach house! 3 min walk to beach!

19. Dream beach home on Lewis Bay with ocean views & amazing outdoor areas

Dream beach home on Lewis Bay with ocean views & amazing outdoor areas
West Yarmouth
9.2 out of 10, Wonderful, (33 reviews)
"Great stay"
United States
Christian Z.
The price is CA $477
CA $1,332 total
includes taxes & fees
Sep 7 - Sep 8
Dream beach home on Lewis Bay with ocean views & amazing outdoor areas

20. Adorable Cape Escape W/ Private Beach Access, Full Kitchen, & Perfect Location

Adorable Cape Escape W/ Private Beach Access, Full Kitchen, & Perfect Location
Dennis Port
9.0 out of 10, Wonderful, (26 reviews)
"Loved this property. "
United States
Carol S.
The price is CA $146
CA $675 total
includes taxes & fees
Sep 1 - Sep 2
Adorable Cape Escape W/ Private Beach Access, Full Kitchen, & Perfect Location
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?

Private Sandy Beach, Truly Oceanfront,Private Decks, Free Kayak, Sleeps 5: This vacation home rental outside of Osterville is located on the beach and has a balcony, a selection of games, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave.

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.