A house by a lake with boats.

Osterville Holiday Rentals

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Osterville holiday 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.
The price is HK$3,335
HK$7,159 total
includes taxes & fees
22 Oct - 23 Oct
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
The price is HK$1,360
HK$1,557 total
includes taxes & fees
1 Nov - 2 Nov
The Club at New Seabury
A kitchen with white cabinetry, a double-door refrigerator, and a glass-fronted cabinet with dishes.

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 HK$2,013
HK$3,229 total
includes taxes & fees
27 Oct - 28 Oct
Serene Haven w/ No Shared Spaces | Cape Cod
A pool area with lounge chairs and flags.

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, (269 reviews)
"The property is an older timeshare and dated."
United States
Kim
The price is HK$1,011
HK$1,157 total
includes taxes & fees
1 Nov - 2 Nov
The Cove at Yarmouth by Westgate Resorts
A sandy beach with a calm lake and a forested hill in the background.

5. 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.
The price is HK$1,727
HK$4,760 total
includes taxes & fees
16 Nov - 17 Nov
Charming 3-bedroom house in lovely Barnstable
A modern kitchen with a large window overlooking a lake, a dining area with chairs, and a living room with a sofa.

6. 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 HK$1,264
HK$3,153 total
includes taxes & fees
4 Nov - 5 Nov
WOW View! Waterfront Cottage. Private Beach, King Bed, Full Kitchen. Relax&Enjoy
A wide sandy beach with footprints leading to the water, a clear sky, and distant buildings.

7. 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.
The price is HK$954
HK$3,793 total
includes taxes & fees
22 Oct - 23 Oct
Cozy Spacious Home Walk to the Beach & 1 Mile to Downtown Hyannis
Private kitchen

8. Entire Hyannis Home - Near Downtown & Beaches

Entire Hyannis Home - Near Downtown & Beaches
Barnstable
8.8 out of 10, Excellent, (3 reviews)
"We had a fantastic stay! The property was extremely clean from top to bottom, which immediately made us feel comfortable settling in. The beds and linens were incredibly comfortable and we all slept great.The location was also a huge plus. It is close to great restaurants, local events and plenty to do in the area, making it easy to get around and enjoy everything nearby.The host was extremely communicative and responsive, which made the whole experience smooth and stress free from booking...
United States
Bethany P.
The price is HK$1,216
HK$3,629 total
includes taxes & fees
16 Nov - 17 Nov
Entire Hyannis Home - Near Downtown & Beaches
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.
The price is HK$3,924
HK$7,661 total
includes taxes & fees
23 Oct - 24 Oct
New construction! Craigville Beach, Main St, Playground, Ice cream/restaurants!!
A beach with clear blue water and a sandy shore.

10. 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.
The price is HK$2,072
HK$5,273 total
includes taxes & fees
22 Oct - 23 Oct
Cape Diem ; All new; 1.5m to Criagville, Hyannis beach; with WiFi, AC
A modern living room with a sofa, chairs, a coffee table, and a dining area.

11. New Seabury Cape Condo + Pool & Beach Escape

New Seabury Cape Condo + Pool & Beach Escape
New Seabury
10.0 out of 10, Exceptional, (92 reviews)
"Great condo, great location. Fully equipped kitchen and awesome patio. "
United States
Jeff V.
New Seabury Cape Condo + Pool & Beach Escape
A kitchen with a central island, white cabinets, a gas stove, and a sink.

12. 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.
The price is HK$3,690
HK$8,679 total
includes taxes & fees
28 Oct - 29 Oct
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.

13. 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)
"We loved staying Conduit. The location is incredible. The lake is gorgeous. We canoed and swam. There are hiking trails across the street. It was 20 minutes to gorgeous beaches. We had 14 of us very comfortably in the house. Stephanie was a great host. We would definitely come back."
United States
Molly R.
The price is HK$3,875
HK$8,917 total
includes taxes & fees
1 Nov - 2 Nov
Lakefront Stunning Cape Cod Views w Private Lake Beach - Backyard is the Lake !
A beach with a boat labeled MS1284HB and a covered area.

14. 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 host, great place!"
United States
Brandon S.
The price is HK$1,091
HK$2,021 total
includes taxes & fees
22 Oct - 23 Oct
Secluded-Entire 2nd floor Suite with Private Bath
A boat docked at a concrete pier with a sandy shore in the background.

15. 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, (45 reviews)
"Great place with kayaks and paddle boards, beach, close to Mashpee Commons. Host was great and place was clean and quaint."
United States
Michele M.
The price is HK$1,236
HK$3,400 total
includes taxes & fees
22 Oct - 23 Oct
Private Waterfront, Beach, Dock, Kayaks, Paddle Boards and Hot Tub!
A garden pathway leading to a house with a stone wall and a wooden gate.

16. 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.
The price is HK$3,767
HK$4,895 total
includes taxes & fees
26 Oct - 27 Oct
Beach Pass Included!
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.
The price is HK$3,728
HK$6,647 total
includes taxes & fees
22 Oct - 23 Oct
Hyannis Hideaway in Cape Cod
A marina with a docked boat, a large industrial building, and a calm water body reflecting the surroundings.

18. 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.
The price is HK$1,976
HK$5,087 total
includes taxes & fees
22 Oct - 23 Oct
Charming Hyannis 3 Bed 2 Bath
A marina with boats docked, a wooden walkway, and a clear blue sky.

19. Hyannis with Waterview [3bd]

Hyannis with Waterview [3bd]
Barnstable
8.0 out of 10, Very good, (3 reviews)
"A very beautiful, modern house. Clean and stocked with all necessary for a comfortable stay. A few minutes walk to pretty beach. 10 minutes walk to ferry harbor and down town . Plenty of restaurants and shops near . We really enjoyed our stay. Pet friendly. Thank you Lloyd"
United States
Eugene C.
The price is HK$1,683
HK$7,199 total
includes taxes & fees
2 Nov - 3 Nov
Hyannis with Waterview [3bd]
A beach with clear water and a sandy shore.

20. New Seabury Home with Private Dock close to Beach, Golf Tennis, BOAT OPTIONAL

New Seabury Home with Private Dock close to Beach, Golf Tennis, BOAT OPTIONAL
Little Neck Bay
9.8 out of 10, Exceptional, (54 reviews)
"We had the best week at 67 Tide Run! The property is gorgeous. We enjoyed kayaking and fishing from the dock. It was plenty big enough for our family of 10. We are going to miss the views. It’s perfect! You cannot go wrong booking Jamie’s home."
United States
cindy w.
The price is HK$3,500
HK$8,138 total
includes taxes & fees
30 Oct - 31 Oct
New Seabury Home with Private Dock close to Beach, Golf Tennis, BOAT OPTIONAL
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

Uncommoner Hotel by Reverie Boutique Collection

Uncommoner Hotel by Reverie Boutique Collection

10/10 Excellent
"The decor is great and it's the rare place that doesn't only value style. Lots of good function too! Thank you for having lots of hooks, many lighting options, and an outlet next to the bed."
Adrienne 1-night trip
Posted 8 hours ago
Uncommoner Hotel by Reverie Boutique Collection

Find out more about Osterville

Search for holiday rentals in Osterville on Expedia! You can easily find your home rentals, villas, holiday apartments in Osterville using one of the methods below:

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  • Enter your travel dates to view the best deals on holiday rentals in Osterville while they last

Look no further and take a look at our great range of rental properties in Osterville!

Frequently asked questions

Can I find holiday rentals in Osterville?

Yes, there are holiday rentals in Osterville close to Stand Up & Paddle Cape Cod, or you can select a more secluded option if you're looking for a relaxing stay.

What are some of the best holiday rentals that Osterville has to offer?

Stunning Oceanfront Home With Amazing Views ~ Private Beach! Ocean Beach Vista!: This holiday home rental outside of Osterville is located on the beach, and has a fireplace, a balcony and a BBQ 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 that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and an arcade/games room.

How many holiday rentals are there in Osterville?

With 59 Expedia holiday rentals, you're guaranteed 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 wider area.

What’s a holiday rental in Osterville like?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Osterville. Holiday rentals offer extras like WiFi and washers and dryers so you'll have a home away from home. If you're concerned about cleanliness, a holiday rental can offer a sense of privacy away from public hotel lifts and lobbies packed with people while still allowing you a great travel experience. You'll also get more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a great option for a family trip or a small group gathering.