A house by a lake with boats.

Search Osterville Cottages

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Save instantly and earn perks with One Key
    Learn about One Key

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
24 Jul - 26 Jul
In two months
4 Sept - 6 Sept
In three months
2 Oct - 4 Oct
In four months
30 Oct - 1 Nov

Our top choices for Osterville cottages

Exterior detail

Charming Antique Boathouse Located Directly On Long Pond.

Charming Antique Boathouse Located Directly On Long Pond.
Plymouth
9.8 out of 10, Exceptional, (116 reviews)
"The hosts were very accommodating. Our arrival was late, and it was easy to get into the boathouse."
United States
Mark P.
Charming Antique Boathouse Located Directly On Long Pond.
Outdoor dining

Walk to Sagamore Beach! Curated + Spacious Cottage

Walk to Sagamore Beach! Curated + Spacious Cottage
Sagamore Beach
10.0 out of 10, Exceptional, (2 reviews)
"everything there we needed. Did not need to buy anything."
United States
JOHN F.
Walk to Sagamore Beach! Curated + Spacious Cottage
Exterior

Walking distance to Private Beach! Charming Cottage North of Cape Cod.

Walking distance to Private Beach! Charming Cottage North of Cape Cod.
Wareham
9.6 out of 10, Exceptional, (14 reviews)
"Enjoyed the stay, would definitely come back!"
United States
Daniel W.
The price is £393
includes taxes & fees
10 Aug - 11 Aug
Walking distance to Private Beach! Charming Cottage North of Cape Cod.
Exterior

1 Mi to Ferry: 'Sea Street Cottage' in Hyannis

1 Mi to Ferry: 'Sea Street Cottage' in Hyannis
Hyannis
8.8 out of 10, Excellent, (19 reviews)
"Perfect weekend getaway- super location. Cozy spot! Loved the area "
United States
Jill S.
1 Mi to Ferry: 'Sea Street Cottage' in Hyannis
Beach

Stay in a TINY HOUSE!★0.4mi to Beach★Village★Restaurants★Pet Friendly ★ 2 bikes!

Stay in a TINY HOUSE!★0.4mi to Beach★Village★Restaurants★Pet Friendly ★ 2 bikes!
Dennis
9.6 out of 10, Exceptional, (115 reviews)
"perfect for couples, clean and pet friendly"
Canada
Jonathan
The price is £302
includes taxes & fees
19 Jul - 20 Jul
Stay in a TINY HOUSE!★0.4mi to Beach★Village★Restaurants★Pet Friendly ★ 2 bikes!
Exterior

Private Cape Cod Cottage. Walk to Ellis Landing Beach!

Private Cape Cod Cottage. Walk to Ellis Landing Beach!
Brewster
10.0 out of 10, Exceptional, (43 reviews)
"Great location - privacy, comfy, and close to the beach!"
United States
Samantha K.
Private Cape Cod Cottage. Walk to Ellis Landing Beach!
Exterior

Small One Bedroom Private Cottage on Large Quiet Property.

Small One Bedroom Private Cottage on Large Quiet Property.
Tisbury
10.0 out of 10, Exceptional, (16 reviews)
"Nice, quaint cottage. Perfect for a couple's getaway! Location was convenient for walking to shops and restaurants."
United States
Randy T.
The price is £385
includes taxes & fees
27 Jul - 28 Jul
Small One Bedroom Private Cottage on Large Quiet Property.
Exterior

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

Charming West Yarmouth Cottage- Minutes to Beaches, Dining & Family Fun
Yarmouth
10.0 out of 10, Exceptional, (2 reviews)
"Cute little cottage. Clean and pull out couch was very comfy! Great stay for a small group. Perfect location near a lot of very nice beaches. Would recommend Gray’s beach for sunset, parking is free!"
United States
Jessica Y.
The price is £430
includes taxes & fees
13 Jul - 14 Jul
Charming West Yarmouth Cottage- Minutes to Beaches, Dining & Family Fun
Exterior

Stylish Cape Cod Cottage 1 mile from Beach, Close to Restaurants!

Stylish Cape Cod Cottage 1 mile from Beach, Close to Restaurants!
Bass River
The price is £532
includes taxes & fees
19 Jul - 20 Jul
Stylish Cape Cod Cottage 1 mile from Beach, Close to Restaurants!
House (3 Bedrooms) | Interior

5 Mi to Beach: Cape Cod Getaway w/ Grill

5 Mi to Beach: Cape Cod Getaway w/ Grill
3.0 star property
Sandwich
The price is £447
includes taxes & fees
20 Jul - 21 Jul
5 Mi to Beach: Cape Cod Getaway w/ Grill
Property grounds

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 £496
includes taxes & fees
8 Aug - 9 Aug
Walk to Swift's Beach! Classic Cottage w/ Deck
Exterior

The Perfect Shore Escape: The Sandpiper

The Perfect Shore Escape: The Sandpiper
Bass River
10.0 out of 10, Exceptional, (2 reviews)
"The location is perfect! Easy access to anywhere on the Cape! Extremely family friendly and a very relaxing atmosphere. Beautiful beach views!"
United States
Michael C.
The price is £512
includes taxes & fees
30 Jul - 31 Jul
The Perfect Shore Escape: The Sandpiper
Exterior

Charming 2BR Coastal Cottage – Walk to Surf Drive Beach & Downtown!

Charming 2BR Coastal Cottage – Walk to Surf Drive Beach & Downtown!
Falmouth
9.4 out of 10, Exceptional, (3 reviews)
"Good location, close to ferry and restaurants. Quiet neighborhood."
United States
Kerry B.
The price is £574
includes taxes & fees
9 Aug - 10 Aug
Charming 2BR Coastal Cottage – Walk to Surf Drive Beach & Downtown!
Exterior

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)
"Great accommodation for what we needed."
United States
Judith F.
The price is £628
includes taxes & fees
20 Jul - 21 Jul
Charming 2-bedroom cottage in fabulous Harwich with WiFi, AC
Exterior

Sundancer – Where Cape Dreams Meet the Sea

Sundancer – Where Cape Dreams Meet the Sea
Bass River
9.0 out of 10, Wonderful, (2 reviews)
"Stay was short but a nice stay. The cottage could use a little updating but was very comfortable and close to the beach."
United States
Tina A.
The price is £485
includes taxes & fees
19 Jul - 20 Jul
Sundancer – Where Cape Dreams Meet the Sea
Property grounds

Entire cottage, walk to/from ferry & downtown, newly renovated, parking on site

Entire cottage, walk to/from ferry & downtown, newly renovated, parking on site
Tisbury
10.0 out of 10, Exceptional, (34 reviews)
"Great place, awesome location!"
United States
Connor B.
The price is £720
includes taxes & fees
14 Jul - 15 Jul
Entire cottage, walk to/from ferry & downtown, newly renovated, parking on site
Exterior

The Book Nook - Drift Into Coastal Calm

The Book Nook - Drift Into Coastal Calm
Bass River
The price is £519
includes taxes & fees
23 Jul - 24 Jul
The Book Nook - Drift Into Coastal Calm
Exterior

LOCATION & QUALITY! Right in town, freshly renovated, near everything u need!

LOCATION & QUALITY! Right in town, freshly renovated, near everything u need!
Tisbury
10.0 out of 10, Exceptional, (59 reviews)
"We loved the location and place was great!"
United States
Eileen M.
The price is £765
includes taxes & fees
18 Jul - 19 Jul
LOCATION & QUALITY! Right in town, freshly renovated, near everything u need!
Terrace/patio

WATERFRONT Downtown Cottage w/ Beach

WATERFRONT Downtown Cottage w/ Beach
Tisbury
10.0 out of 10, Exceptional, (50 reviews)
"Very beautiful, very clean with incredible views of the Vineyard Haven harbor views"
United States
John M.
The price is £923
includes taxes & fees
13 Jul - 14 Jul
WATERFRONT Downtown Cottage w/ Beach
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

Heritage House Inn on Cape Cod, an Ascend Collection Hotel

Heritage House Inn on Cape Cod, an Ascend Collection Hotel

8/10 Good
"The rooms and service were very good. The Heritage should have separate coffee/breakfast amenities from the sister Comfort Inn. At least, a higher level of complimentary coffee. The pools need maintenance."
Pramita 2-night trip
Posted less than an hour ago
Heritage House Inn on Cape Cod, an Ascend Collection Hotel

Find out more about Osterville

Osterville Cottages information

Number of reviews
432
Accommodation
627 Cottages
Lowest Price
£302
Highest Price
£923

Frequently asked questions

How much do cottages in Osterville cost?
Cottages in Osterville range between £302 and £923 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 great place to relax and recharge between adventures. This 2.5-star cottage also offers a barbecue grill and a swimming pool. 11 Mashpee - 2 Bedroom Cottage is another leading option with visitors to the area. It has a 3-star rating and amenities including a barbecue grill and a playground.
How many cottages are there in Osterville?
There are 627 cottages in Osterville. No matter if you're travelling with the little ones or organising 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?
Settle in at Sun Retreats Peters Pond, a 2.5-star cottage not far from downtown. Conveniences here include a playground and a picnic area. Another family-friendly option where you can swap the urban jungle for wide open spaces is 11 Mashpee - 2 Bedroom Cottage. A playground and WiFi help make this 3-star cottage a traveller favourite. Osterville boasts an array of family-friendly attractions to explore when you need to keep the kids busy. Cahoon Museum of American Art and Edward Gorey House guarantee fun for travellers of all ages.
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 traveller 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.