A house by a lake with boats.

Osterville Holiday Rentals

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 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 AU$1,281
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 AU$285
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 AU$580
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 AU$173
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 AU$865
includes taxes & fees
15 Nov - 16 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 AU$585
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 AU$721
includes taxes & fees
2 Nov - 3 Nov
Cozy Spacious Home Walk to the Beach & 1 Mile to Downtown Hyannis
A beach with a boat labeled MS1284HB and a covered area.

8. 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 AU$280
includes taxes & fees
31 Oct - 1 Nov
Secluded-Entire 2nd floor Suite with Private Bath
A modern living room with a sofa, chairs, a coffee table, and a dining area.

9. 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.
The price is AU$455
includes taxes & fees
22 Oct - 23 Oct
New Seabury Cape Condo + Pool & Beach Escape
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 AU$971
includes taxes & fees
17 Oct - 18 Oct
Cape Diem ; All new; 1.5m to Criagville, Hyannis beach; with WiFi, AC
A modern kitchen with a large island, stainless steel appliances, and grey cabinetry.

11. 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 AU$1,356
includes taxes & fees
19 Oct - 20 Oct
New construction! Craigville Beach, Main St, Playground, Ice cream/restaurants!!
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 AU$1,557
includes taxes & fees
18 Oct - 19 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)
"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.
The price is AU$1,617
includes taxes & fees
20 Oct - 21 Oct
Lakefront Stunning Cape Cod Views w Private Lake Beach - Backyard is the Lake !
A boat docked at a concrete pier with a sandy shore in the background.

14. 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 AU$610
includes taxes & fees
18 Oct - 19 Oct
Private Waterfront, Beach, Dock, Kayaks, Paddle Boards and Hot Tub!
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.
The price is AU$653
includes taxes & fees
18 Oct - 19 Oct
Beach Pass Included!
A wooden deck with a wooden bench, a railing, and a window.

16. 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 AU$1,178
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.

17. 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 AU$907
includes taxes & fees
18 Oct - 19 Oct
Charming Hyannis 3 Bed 2 Bath
A bedroom with a bed, a dresser, a sofa, and a painting on the wall.

18. Charming studio in tranquil Falmouth with AC

Charming studio in tranquil Falmouth with AC
Falmouth
10.0 out of 10, Exceptional, (4 reviews)
"Very clean and comfy place, a short drive to Falmouth center! Communication was very easy and check-in simple."
United States
Harry H.
The price is AU$346
includes taxes & fees
18 Oct - 19 Oct
Charming studio in tranquil Falmouth with AC
A room with a sloped ceiling, wooden walls, a bed with red towels, a white dresser, and an air conditioning unit.

19. Charming Family-friendly Getaway in Sandwich!

Charming Family-friendly Getaway in Sandwich!
3.0 star property
Sandwich
The price is AU$618
includes taxes & fees
18 Oct - 19 Oct
Charming Family-friendly Getaway in Sandwich!
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

Iris Hotel Cape Cod

Iris Hotel Cape Cod

8/10 Good
"Great pet friendly hotel. Continental breakfast very good. Staff very friendly and helpful. Room very clean but bath tub needs updating( non skid strips with ground in dirt, which looks like from many years of use). Loved the Iris colored decor, even the lighting outside is purple!Could use more outlets on night stand - there are only 2 and we have iPhones and smart watches that needed to be charged. Mattress was comfortable as well as the pillows. The only real problem we found was that you could not watch any scheduled TV programs, just older shows. Thousands of channels to watch, but no local live news and unable to watch shows in the new fall lineup on CBS, NBC & ABC. Very frustrating trying to figure out controls. TV is a nice big flat screen ( looks to be about 65”) but you have to have an account for many of the channels with Netflix, Disney plus, Roku, Hulu,Apple TV , etc. just wanted to watch reg TV, not recent repeats or clips from older shows."
Wayne 3-night trip
Posted 6 hours ago
Iris Hotel Cape Cod

Find out more about Osterville

Everything you need to know about Osterville holiday rentals

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

Osterville holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depend on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Osterville holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Osterville holiday rentals we have selected for you start as low as AU$173 per night. Entering your travel dates in the search wizard might find you even better deals!

How to find incredible deals on Osterville rentals

At Expedia, we put the best Osterville holiday 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 holiday.

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 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.