A house by a lake with boats.

Search Osterville Cottage Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

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

Our top choices for Osterville cottages

A house surrounded by dense forest, overlooking a body of water.

1. 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 ￥24,042
￥62,093 total
includes taxes & fees
Nov 14 - Nov 15
WOW View! Waterfront Cottage. Private Beach, King Bed, Full Kitchen. Relax&Enjoy
A house with a deck, a flag, and a garage.

2. Charming West Yarmouth Cottage- Minutes to Beaches, Dining & Family Fun

Charming West Yarmouth Cottage- Minutes to Beaches, Dining & Family Fun
Yarmouth
9.4 out of 10, Exceptional, (9 reviews)
"Great stay the cottage was very clean and welcoming"
United States
Alex r.
Charming West Yarmouth Cottage- Minutes to Beaches, Dining & Family Fun
A single-story house with a front door, a small porch, and a fenced yard.

3. Charming Family-friendly Getaway in Sandwich!

Charming Family-friendly Getaway in Sandwich!
3.0 star property
Sandwich
The price is ￥21,827
￥68,164 total
includes taxes & fees
Oct 25 - Oct 26
Charming Family-friendly Getaway in Sandwich!
A house with a front porch, a small garden, and a mailbox.

4. Cozy, vacation home in a charming duplex cottage

Cozy, vacation home in a charming duplex cottage
Yarmouth
9.6 out of 10, Exceptional, (10 reviews)
"Cozy small home perfect for a girls weekend! Close proximity to the ferries and several good restaurants close by!"
United States
Sue N.
The price is ￥31,634
￥67,887 total
includes taxes & fees
Nov 1 - Nov 2
Cozy, vacation home in a charming duplex cottage
A single-story house with a front porch, a garage, and a small front yard.

5. Peaceful Coastal Cottage Near Plymouth & Cape Cod

Peaceful Coastal Cottage Near Plymouth & Cape Cod
Wareham
9.8 out of 10, Exceptional, (17 reviews)
"Enjoyed the stay, would definitely come back!"
United States
Daniel W.
The price is ￥13,444
￥60,599 total
includes taxes & fees
Nov 4 - Nov 5
Peaceful Coastal Cottage Near Plymouth & Cape Cod
A covered outdoor patio with a table and chairs, a pergola, and a view of neighboring houses.

6. Walk to Swift's Beach! Classic Cottage w/ Deck

Walk to Swift's Beach! Classic Cottage w/ Deck
Wareham
9.8 out of 10, Exceptional, (6 reviews)
"The cottage was clean comfortable and quiet. We loved sitting out on the back deck. The beach was a short walk and very beautiful. We enjoyed our stay."
United States
Marylyn P.
The price is ￥14,710
￥71,200 total
includes taxes & fees
Nov 3 - Nov 4
Walk to Swift's Beach! Classic Cottage w/ Deck
A single-story house with a gabled roof, a front porch, and a small front yard.

7. Charming 2-bedroom cottage in fabulous Harwich with WiFi, AC

Charming 2-bedroom cottage in fabulous Harwich with WiFi, AC
Harwich
9.0 out of 10, Wonderful, (6 reviews)
"would stay here again"
United States
david r.
The price is ￥36,563
￥78,439 total
includes taxes & fees
Oct 27 - Oct 28
Charming 2-bedroom cottage in fabulous Harwich with WiFi, AC
A covered outdoor patio with a table and chairs, a pergola, and a view of neighboring houses.

8. Walk to Swift's Beach! Classic Cottage w/ Deck

Walk to Swift's Beach! Classic Cottage w/ Deck
3.0 star property
Wareham
10.0 out of 10, Exceptional, (1 review)
"3 of us had a great time in Wareham. The cottage was exactly as advertised and close to many beaches"
United States
Tracy
The price is ￥20,878
￥69,787 total
includes taxes & fees
Nov 4 - Nov 5
Walk to Swift's Beach! Classic Cottage w/ Deck
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

Margaritaville Resort Cape Cod

Margaritaville Resort Cape Cod

8/10 Good
"Overall, the hotel and our room were lovely. There was a large event taking place during our stay, and a significant number of younger guests from the event were gathered throughout the public areas. While completely understandable, it did make it difficult for us to enjoy those spaces. Our only real disappointment was breakfast. We needed something quick and were directed to the to-go area, but waited more than 20 minutes for a simple breakfast sandwich. When it was made incorrectly, the interaction felt unnecessarily dismissive and we were made to feel as though the mistake was our fault. A little more customer-service-minded handling would have made a big difference. Aside from that experience, we had a lovely room and enjoyed our stay overall."
Anne 4-night trip
Posted 2 hours ago
Margaritaville Resort Cape Cod

Find out more about Osterville

Osterville Cottages information

Number of reviews
53
Accommodation
608 Cottages
Lowest Price
￥60,599
Highest Price
￥78,439

Frequently asked questions

How much do cottages in Osterville cost?
Cottages in Osterville range between ￥60,599 and ￥78,439 per night. These properties offer a chance to get reacquainted with nature — at a price you can afford. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
What are the best cottages in Osterville?
Take your pick of multiple cottages in Osterville with a total average guest review rating of 9.7. Sun Retreats Peters Pond is a terrific place to relax and put your feet up between adventures. This 2.5-star cottage also offers a barbecue grill and a swimming pool. 11 Mashpee - 2 Bedroom Cottage is another popular pick with travelers to the area. It has a 3-star rating and amenities including a barbecue grill and a golf course.
How many cottages are there in Osterville?
There are 608 cottages in Osterville. No matter if you're traveling with the little ones or organizing a weekend retreat with your pals, Expedia will help you find the right place to immerse yourself in nature.
Are there any family-friendly cottages in Osterville?
Many visitors searching for a family-friendly cottage in Osterville go for Sun Retreats Peters Pond. With a 2.5-star rating and amenities like a playground and WiFi, you'll get a good night's rest here. Another noteworthy pick for families who crave time out close to nature is 11 Mashpee - 2 Bedroom Cottage. A playground and an oven help make this 3-star cottage a great base for your Osterville trip. Once you've checked in and unpacked your bags, there are loads of family-friendly attractions to discover in and around Osterville. Cape Cod Inflatable Park and Cape Codder Water Park guarantee a good time for young and old.
Why book your cottage in Osterville with Expedia?
Booking a cottage in Osterville is as easy as deciding on your travel dates and picking your ideal place for outdoor relaxation and recreation. From ritzy retreats to low-cost properties and cottages that have perks like free WiFi, Expedia has something for all traveler styles. As for the best deals around? We've got you covered!
How can I find cheap cottages in Osterville?
A great way to get cheap cottages in Osterville is with Expedia's useful filter tool. Narrow down your search by budget, star rating and amenities to secure unbeatable prices in just a few keystrokes.
What is there to do in Osterville near my cottage?
The ideal travel accessory is a well-planned schedule. Dowses Beach is a wonderful place to kick-start your sightseeing in Osterville.