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Our top choices for Osterville holiday homes

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)
"Denise was an amazing host and very welcoming! We can’t wait to go back next year!"
United States
Carrie B.
The price is HK$3,805
HK$7,344 total
includes taxes & fees
14 Nov - 15 Nov
Beach pass included • Modern 3BR Osterville retreat, walkable to village center

2. Great Home Close to Craigville Beach

Great Home Close to Craigville Beach
Barnstable
10.0 out of 10, Exceptional, (17 reviews)
"Easy booking very clean and convenient for our families wedding event"
United States
James B.
The price is HK$2,118
HK$4,588 total
includes taxes & fees
19 Nov - 20 Nov
Great Home Close to Craigville Beach

3. Historic 5BR Mid Cape w/ Private Lake Access

Historic 5BR Mid Cape w/ Private Lake Access
Barnstable
10.0 out of 10, Exceptional, (2 reviews)
"We absolutely loved it!!!"
United States
Camila P.
The price is HK$1,569
HK$4,499 total
includes taxes & fees
16 Nov - 17 Nov
Historic 5BR Mid Cape w/ Private Lake Access

4. 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$1,098
HK$3,970 total
includes taxes & fees
14 Dec - 15 Dec
Cozy Spacious Home Walk to the Beach & 1 Mile to Downtown Hyannis

5. 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$1,961
HK$2,442 total
includes taxes & fees
14 Dec - 15 Dec
Beach Pass Included!

6. 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 in a wonderful location!"
United States
Jamie C.
The price is HK$3,922
HK$7,308 total
includes taxes & fees
14 Dec - 15 Dec
New construction! Craigville Beach, Main St, Playground, Ice cream/restaurants!!

7. Sal's Place

Sal's Place
2.0 star property
Hyannis
The price is HK$1,961
HK$3,186 total
includes taxes & fees
14 Dec - 15 Dec
Sal's Place

8. Cozy 3BR 2 Ba Home, Mins to Sandwich Center, Mashpee, Ocean & Fresh Water Beach

Cozy 3BR 2 Ba Home, Mins to Sandwich Center, Mashpee, Ocean & Fresh Water Beach
Sandwich
The price is HK$1,569
HK$2,927 total
includes taxes & fees
14 Nov - 15 Nov
Cozy 3BR 2 Ba Home, Mins to Sandwich Center, Mashpee, Ocean & Fresh Water Beach

9. 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$3,883
HK$8,413 total
includes taxes & fees
14 Nov - 15 Nov
Spacious Lake House for Large Groups w Private Acre+ short path to Lake

10. Entire Hyannis Home - Near Downtown & Beaches

Entire Hyannis Home - Near Downtown & Beaches
Barnstable
8.6 out of 10, Excellent, (4 reviews)
"We had a lovely stay! The location was great, with plenty of bars and restaurants nearby. The place was clean, spacious and had everything we needed. Rebecca made the whole process really easy from start to finish. Thank you for a lovely stay!"
United Kingdom
Ellie M.
The price is HK$1,389
HK$3,681 total
includes taxes & fees
1 Dec - 2 Dec
Entire Hyannis Home - Near Downtown & Beaches

11. 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$4,077
HK$8,653 total
includes taxes & fees
14 Nov - 15 Nov
Lakefront Stunning Cape Cod Views w Private Lake Beach - Backyard is the Lake !

12. 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$3,264 total
includes taxes & fees
15 Nov - 16 Nov
Private Waterfront, Beach, Dock, Kayaks, Paddle Boards and Hot Tub!

13. Luxurious 7BR Estate Includes - Tennis Crt, Pool, Hot Tub, Home Theater, & Gym!

Luxurious 7BR Estate Includes - Tennis Crt, Pool, Hot Tub, Home Theater, & Gym!
West Barnstable
10.0 out of 10, Exceptional, (150 reviews)
"Great fit for our family!"
United States
William H.
The price is HK$7,766
HK$13,019 total
includes taxes & fees
23 Nov - 24 Nov
Luxurious 7BR Estate Includes - Tennis Crt, Pool, Hot Tub, Home Theater, & Gym!

14. Hyannis Hideaway in Cape Cod

Hyannis Hideaway in Cape Cod
Barnstable
9.8 out of 10, Exceptional, (11 reviews)
"Property was very clean, towels and linen provded. Nice quiet neighborhood and plenty of bedrooms"
United States
Mari C.
The price is HK$3,726
HK$6,339 total
includes taxes & fees
18 Nov - 19 Nov
Hyannis Hideaway in Cape Cod

15. Charming Family-Friendly Getaway in Sandwich!

Charming Family-Friendly Getaway in Sandwich!
Sandwich
The price is HK$518
HK$2,954 total
includes taxes & fees
15 Nov - 16 Nov
Charming Family-Friendly Getaway in Sandwich!

16. 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$1,759
HK$6,934 total
includes taxes & fees
15 Nov - 16 Nov
Hyannis with Waterview [3bd]

17. Spacious 4BR Cape Escape! Modern Tranquil house close to town, beaches, shops

Spacious 4BR Cape Escape! Modern Tranquil house close to town, beaches, shops
Falmouth
10.0 out of 10, Exceptional, (19 reviews)
"Jessica was absolutely amazing and so was the house! We stayed here for our family vacation and it was perfect. 5 stars all around!"
United States
Kelsey B.
The price is HK$2,581
HK$6,455 total
includes taxes & fees
12 Dec - 13 Dec
Spacious 4BR Cape Escape! Modern Tranquil house close to town, beaches, shops

18. Summers by the Pool - Barnstable Village, Cape Cod, MA Home w/Pool + Beach Pass!

Summers by the Pool - Barnstable Village, Cape Cod, MA Home w/Pool + Beach Pass!
Barnstable
10.0 out of 10, Exceptional, (15 reviews)
"Excellent Host!!!"
United States
TRP L.
The price is HK$6,668
HK$11,941 total
includes taxes & fees
14 Nov - 15 Nov
Summers by the Pool - Barnstable Village, Cape Cod, MA Home w/Pool + Beach Pass!

19. Cape Cod Hyannis Rendezvous'

Cape Cod Hyannis Rendezvous'
Barnstable
10.0 out of 10, Exceptional, (18 reviews)
"Location was great, we were able to walk right into town! Overall great stay!"
United States
Whitney M.
The price is HK$4,151
HK$6,960 total
includes taxes & fees
16 Nov - 17 Nov
Cape Cod Hyannis Rendezvous'

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$4,315
HK$9,113 total
includes taxes & fees
14 Nov - 15 Nov
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.

Learn more about Osterville

Elegant boutiques and seafood restaurants line Main Street in this charming Cape Cod village with New England coastal appeal. Spend sunny afternoons at Joshua's Pond or Dowses Beach, where calm waters welcome swimmers and kayakers.

Storefronts with signs for Coastal Style, Sara Campbell, and Oyster Island Emporium.