A house by a lake with boats.

Osterville Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Osterville vacation rentals

A beach with a clear sky and a lifeguard tower in the distance.

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, (24 reviews)
"Very comfortable, close to town, all around great stay."
United States
Elizabeth C.
$800 nightly
The price is $916
Oct 8 - Oct 9
Total with taxes and fees
Beach pass included • Modern 3BR Osterville retreat, walkable to village center
A coastal hotel with multiple beachside rooms, a large covered area, and a beach with umbrellas.

2. The Club at New Seabury

The Club at New Seabury
3.5 star property
New Seabury
9.0 out of 10, Wonderful, (371 reviews)
"The New Seabury resort is beautiful & has excellent customer service. The 4/5 stars is because the unit we stayed in needs some updating. However, the layout, cleanliness, & location is good."
United States
Kathleen
$147 nightly
The price is $169
Nov 1 - Nov 2
Total with taxes and fees
The Club at New Seabury
A pool area with lounge chairs and flags.

3. 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, (269 reviews)
"The property is an older timeshare and dated."
United States
Kim
$105 nightly
The price is $120
Nov 2 - Nov 3
Total with taxes and fees
The Cove at Yarmouth by Westgate Resorts
A kitchen with white cabinetry, a double-door refrigerator, and a glass-fronted cabinet with dishes.

4. 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.
$360 nightly
The price is $411
Oct 12 - Oct 13
Total with taxes and fees
Serene Haven w/ No Shared Spaces | Cape Cod
A wooden deck with a table and chairs, surrounded by a wooden fence and large windows.

5. Classic Cape Escape in Charming Cotuit

Classic Cape Escape in Charming Cotuit
Contuit
9.0 out of 10, Wonderful, (6 reviews)
"Loved the location and walking path across the way. Very comfortable and spacious home. Would definitely revisit again. "
United States
Michelle
Classic Cape Escape in Charming Cotuit
A wide sandy beach with footprints leading to the water, a clear sky, and distant buildings.

6. 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
9.0 out of 10, Wonderful, (11 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.
$437 nightly
The price is $483
Oct 8 - Oct 9
Total with taxes and fees
Cozy Spacious Home Walk to the Beach & 1 Mile to Downtown Hyannis
A sandy beach with a calm lake and a forested hill in the background.

7. Charming 3-bedroom house in lovely Barnstable

Charming 3-bedroom house in lovely Barnstable
Barnstable
9.6 out of 10, Exceptional, (5 reviews)
"Excellent stay! Loved the home! "
United States
Cailee B.
$574 nightly
The price is $657
Oct 12 - Oct 13
Total with taxes and fees
Charming 3-bedroom house in lovely Barnstable
A modern living room with a sofa, chairs, a coffee table, and a dining area.

8. New Seabury Cape Condo + Pool & Beach Escape

New Seabury Cape Condo + Pool & Beach Escape
New Seabury
10.0 out of 10, Exceptional, (91 reviews)
"Great condo, great location. Fully equipped kitchen and awesome patio. "
United States
Jeff V.
$280 nightly
The price is $321
Oct 14 - Oct 15
Total with taxes and fees
New Seabury Cape Condo + Pool & Beach Escape
A modern kitchen with a large island, stainless steel appliances, and grey cabinetry.

9. 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, (41 reviews)
"Beautiful home"
United States
steven c.
$853 nightly
The price is $976
Oct 19 - Oct 20
Total with taxes and fees
New construction! Craigville Beach, Main St, Playground, Ice cream/restaurants!!
A modern kitchen with a large window overlooking a lake, a dining area with chairs, and a living room with a sofa.

10. 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.
$376 nightly
The price is $430
Nov 6 - Nov 7
Total with taxes and fees
WOW View! Waterfront Cottage. Private Beach, King Bed, Full Kitchen. Relax&Enjoy
A beach with a boat labeled MS1284HB and a covered area.

11. Secluded-Entire 2nd floor Suite with Private Bath

Secluded-Entire 2nd floor Suite with Private Bath
Barnstable
9.2 out of 10, Wonderful, (5 reviews)
"Great, very close to downtown hyannis. Charming and a nice owner. "
United States
sam s.
$201 nightly
The price is $230
Oct 11 - Oct 12
Total with taxes and fees
Secluded-Entire 2nd floor Suite with Private Bath
A beach with clear blue water and a sandy shore.

12. Cape Diem ; All new; 1.5m to Criagville, Hyannis beach; with WiFi, AC

Cape Diem ; All new; 1.5m to Criagville, Hyannis beach; with WiFi, AC
Barnstable
10.0 out of 10, Exceptional, (7 reviews)
"Very nice property in a quiet and convenient location. Private backyard with outdoor shower. Interior was completely updated with very nice furnishings and appliances. All in all a great home that we will definitely return to. "
United States
Jim C.
$585 nightly
The price is $670
Oct 8 - Oct 9
Total with taxes and fees
Cape Diem ; All new; 1.5m to Criagville, Hyannis beach; with WiFi, AC
A kitchen with a central island, white cabinets, a gas stove, and a sink.

13. Spacious Lake House for Large Groups w Private Acre+ short path to Lake

Spacious Lake House for Large Groups w Private Acre+ short path to Lake
Barnstable
8.4 out of 10, Very good, (10 reviews)
"Easy check in, lots of room for people. Needs a little updating and it will be perfect."
United States
Austin S.
$966 nightly
The price is $1,106
Oct 28 - Oct 29
Total with taxes and fees
Spacious Lake House for Large Groups w Private Acre+ short path to Lake
A wooden deck with a table and chairs, overlooking a body of water and trees.

14. Lakefront Stunning Cape Cod Views w Private Lake Beach - Backyard is the Lake !

Lakefront Stunning Cape Cod Views w Private Lake Beach - Backyard is the Lake !
Barnstable
7.6 out of 10, Good, (5 reviews)
"My family and I thoroughly enjoyed our week long stay at the beautiful property. There were 12 of us and we were extremely comfortable, with plenty of space to gather and sleep. The property sits on a quiet pond, that was perfect for swimming and canoeing. We had our own little piece of paradise. There are canoes for use, several decks for lounging and was within a short distance to various shops and a grocery store just a few minutes away. The host was in constant contact with us, making sure...
United States
Madilynn B.
$993 nightly
The price is $1,136
Oct 8 - Oct 9
Total with taxes and fees
Lakefront Stunning Cape Cod Views w Private Lake Beach - Backyard is the Lake !
A hot tub under a wooden pergola with string lights, surrounded by a garden and a pool.

15. Beach Pass Included!

Beach Pass Included!
Barnstable
9.4 out of 10, Exceptional, (3 reviews)
"The property is gorgeous and inviting from the second you pull in the driveway to the inside of the house. The spacious, fenced in yard was a great feature when traveling with kids and pets. The pool and hot tub kept us entertained the whole vacation; we barely felt the need to leave the house!"
United States
Sara D.
$406 nightly
The price is $465
Oct 12 - Oct 13
Total with taxes and fees
Beach Pass Included!
A boat docked at a concrete pier with a sandy shore in the background.

16. Private Waterfront, Beach, Dock, Kayaks, Paddle Boards and Hot Tub!

Private Waterfront, Beach, Dock, Kayaks, Paddle Boards and Hot Tub!
Seconsett Island
10.0 out of 10, Exceptional, (44 reviews)
"Great stay!"
United States
Kian S.
$398 nightly
The price is $456
Oct 18 - Oct 19
Total with taxes and fees
Private Waterfront, Beach, Dock, Kayaks, Paddle Boards and Hot Tub!
A wooden deck with a wooden bench, a railing, and a window.

17. Hyannis Hideaway in Cape Cod

Hyannis Hideaway in Cape Cod
Barnstable
9.8 out of 10, Exceptional, (11 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.
$659 nightly
The price is $754
Oct 8 - Oct 9
Total with taxes and fees
Hyannis Hideaway in Cape Cod
A wooden-paneled room with a sofa, chairs, a table, a fireplace, and a clock.

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

Adorable Cape Escape W/ Private Beach Access, Full Kitchen, & Perfect Location
Dennis Port
9.2 out of 10, Wonderful, (27 reviews)
"Property is convenient to beaches and restaurants."
United States
Laurie and Rick A.
$385 nightly
The price is $441
Oct 8 - Oct 9
Total with taxes and fees
Adorable Cape Escape W/ Private Beach Access, Full Kitchen, & Perfect Location
A beach with a wooden structure, clear sky, and calm sea.

19. 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, (69 reviews)
"Great location, would stay here again!"
United States
Kinde O.
$521 nightly
The price is $596
Oct 14 - Oct 15
Total with taxes and fees
SANDTRAP! BEACH short walk! Marinas, Golf, Shopping & Restaurants short drive!
A marina with a docked boat, a large industrial building, and a calm water body reflecting the surroundings.

20. Charming Hyannis 3 Bed 2 Bath

Charming Hyannis 3 Bed 2 Bath
Barnstable
9.2 out of 10, Wonderful, (15 reviews)
"We enjoyed our few days in the Cape Cod area. The unit was clean and comfortable, close to attractions, restaurants and main roads."
United States
Daniel G.
$604 nightly
The price is $652
Oct 8 - Oct 9
Total with taxes and fees
Charming Hyannis 3 Bed 2 Bath
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Osterville Hotel Reviews

Iris Hotel Cape Cod

Iris Hotel Cape Cod

10/10 Excellent
"The Iris hotel was a good stay. I liked how the room smelled fresh, and the hallways smelled of new carpet. The bathroom was small and showed signs of being a little but it was manageable and the breakfast was great."
Ron 2-night trip
Posted 15 hours ago
Iris Hotel Cape Cod

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 $120 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?

Stunning Oceanfront Home With Amazing Views ~ Private Beach! Ocean Beach Vista!: This vacation home rental outside of Osterville is located on the beach and has a fireplace, a balcony, 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. Kick off your shoes and enjoy yourself with a garden and an arcade game room.

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.