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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 centerOsterville
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!"
Carrie B.
The price is £705
includes taxes & fees
15 Nov - 16 Nov
2. Great Home Close to Craigville Beach
Great Home Close to Craigville BeachBarnstable
10.0 out of 10, Exceptional, (17 reviews)
"Easy booking very clean and convenient for our families wedding event"
James B.
The price is £446
includes taxes & fees
24 Nov - 25 Nov
3. Historic 5BR Mid Cape w/ Private Lake Access
Historic 5BR Mid Cape w/ Private Lake AccessBarnstable
10.0 out of 10, Exceptional, (2 reviews)
"We absolutely loved it!!!"
Camila P.
The price is £442
includes taxes & fees
16 Nov - 17 Nov
4. Cozy Spacious Home Walk to the Beach & 1 Mile to Downtown Hyannis
Cozy Spacious Home Walk to the Beach & 1 Mile to Downtown HyannisBarnstable
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."
Jen M.
The price is £380
includes taxes & fees
18 Nov - 19 Nov
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!"
Sara D.
The price is £236
includes taxes & fees
15 Nov - 16 Nov
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!"
Jamie C.
The price is £697
includes taxes & fees
15 Nov - 16 Nov
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 BeachSandwich
The price is £285
includes taxes & fees
15 Nov - 16 Nov
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 LakeBarnstable
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."
Austin S.
The price is £815
includes taxes & fees
15 Nov - 16 Nov
10. Entire Hyannis Home - Near Downtown & Beaches
Entire Hyannis Home - Near Downtown & BeachesBarnstable
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!"
Ellie M.
The price is £359
includes taxes & fees
18 Nov - 19 Nov
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."
Molly R.
The price is £838
includes taxes & fees
15 Nov - 16 Nov
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."
Michele M.
The price is £336
includes taxes & fees
15 Nov - 16 Nov
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!"
William H.
The price is £1,312
includes taxes & fees
24 Nov - 25 Nov
14. Hyannis Hideaway in Cape Cod
Hyannis Hideaway in Cape CodBarnstable
9.8 out of 10, Exceptional, (11 reviews)
"Property was very clean, towels and linen provded. Nice quiet neighborhood and plenty of bedrooms"
Mari C.
The price is £616
includes taxes & fees
15 Nov - 16 Nov
15. Charming Family-Friendly Getaway in Sandwich!
Charming Family-Friendly Getaway in Sandwich!Sandwich
The price is £281
includes taxes & fees
15 Nov - 16 Nov
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"
Eugene C.
The price is £663
includes taxes & fees
15 Nov - 16 Nov
17. Spacious 4BR Cape Escape! Modern Tranquil house close to town, beaches, shops
Spacious 4BR Cape Escape! Modern Tranquil house close to town, beaches, shopsFalmouth
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!"
Kelsey B.
The price is £597
includes taxes & fees
1 Dec - 2 Dec
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!!!"
TRP L.
The price is £1,126
includes taxes & fees
15 Nov - 16 Nov
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!"
Whitney M.
The price is £665
includes taxes & fees
18 Nov - 19 Nov
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 OPTIONALLittle 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."
cindy w.
The price is £881
includes taxes & fees
21 Nov - 22 Nov
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.
Top reviews in Osterville
Hyannis Travel Inn
Hyannis Travel InnHyannis
10/10 Excellent
Great stay.
Fantastic location for harbour and Hy-line and eating establishments.
Accommodation was excellent and super value for money. The staff bent over backwards to help and support. I wish we’d stayed here longer and bypassed Rhode Island!
Lindsey
