Osterville Vacation Homes

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Our top choices for Osterville holiday homes

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

Osterville

Elizabeth C.

HK$7,185 total

includes taxes & fees

9 Oct - 10 Oct

A wooden deck with a table and chairs, surrounded by a wooden fence and large windows.

2. Classic Cape Escape in Charming Cotuit

Contuit

Michelle

A sandy beach with a calm lake and a forested hill in the background.

3. Charming 3-bedroom house in lovely Barnstable

Barnstable

Cailee B.

HK$5,120 total

includes taxes & fees

13 Oct - 14 Oct

A bedroom with a bed, nightstands, a lamp, and two windows with views of trees.

4. Cozy Spacious Home Walk to the Beach & 1 Mile to Downtown Hyannis

Barnstable

Jen M.

HK$3,971 total

includes taxes & fees

13 Oct - 14 Oct

A modern kitchen with a large island, stainless steel appliances, and grey cabinetry.

5. New construction! Craigville Beach, Main St, Playground, Ice cream/restaurants!!

Barnstable

steven c.

HK$7,661 total

includes taxes & fees

20 Oct - 21 Oct

6. Entire Hyannis Home - Near Downtown & Beaches

Barnstable

"We had a fantastic stay! The property was extremely clean from top to bottom, which immediately made us feel comfortable settling in. The beds and linens were incredibly comfortable and we all slept great.The location was also a huge plus. It is close to great restaurants, local events and plenty to do in the area, making it easy to get around and enjoy everything nearby.The host was extremely communicative and responsive, which made the whole experience smooth and stress free from booking...

Bethany P.

HK$3,880 total

includes taxes & fees

25 Oct - 26 Oct

A beach with clear blue water and a sandy shore.

7. Cape Diem ; All new; 1.5m to Criagville, Hyannis beach; with WiFi, AC

Barnstable

Jim C.

HK$5,254 total

includes taxes & fees

12 Oct - 13 Oct

A kitchen with a central island, white cabinets, a gas stove, and a sink.

8. Spacious Lake House for Large Groups w Private Acre+ short path to Lake

Barnstable

Austin S.

HK$8,679 total

includes taxes & fees

28 Oct - 29 Oct

A wooden deck with a table and chairs, overlooking a body of water and trees.

9. Lakefront Stunning Cape Cod Views w Private Lake Beach - Backyard is the Lake !

Barnstable

"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...

Madilynn B.

HK$8,917 total

includes taxes & fees

12 Oct - 13 Oct

A hot tub under a wooden pergola with string lights, surrounded by a garden and a pool.

10. Beach Pass Included!

Barnstable

Sara D.

HK$3,647 total

includes taxes & fees

13 Oct - 14 Oct

A beach with sand, flowers, and a clear sky.

11. Sal's Place

Hyannis

HK$4,175 total

includes taxes & fees

12 Oct - 13 Oct

A boat docked at a concrete pier with a sandy shore in the background.

12. Private Waterfront, Beach, Dock, Kayaks, Paddle Boards and Hot Tub!

Seconsett Island

Kian S.

HK$3,575 total

includes taxes & fees

18 Oct - 19 Oct

A wooden deck with a wooden bench, a railing, and a window.

13. Hyannis Hideaway in Cape Cod

Barnstable

Hunter W.

HK$6,646 total

includes taxes & fees

10 Oct - 11 Oct

A marina with boats docked, a wooden walkway, and a clear blue sky.

14. Hyannis with Waterview [3bd]

Barnstable

Eugene C.

HK$7,199 total

includes taxes & fees

2 Nov - 3 Nov

A beach with a wooden structure, clear sky, and calm sea.

15. SANDTRAP! BEACH short walk! Marinas, Golf, Shopping & Restaurants short drive!

Yarmouth

Kinde O.

HK$4,679 total

includes taxes & fees

14 Oct - 15 Oct

A modern kitchen with white cabinetry, stainless steel appliances, a large island, and a view of greenery outside.

16. WALK to the Beach + FirePit, Bikes, Paddleboards - Modern House

Yarmouth

Hailey B.

HK$3,998 total

includes taxes & fees

18 Oct - 19 Oct

17. Walk to the Beach - Modern Home w/ FirePit, Bikes, Office, Grill + More!

Yarmouth

Allison V.

HK$5,268 total

includes taxes & fees

18 Oct - 19 Oct

A beach with clear water and a sandy shore.

18. New Seabury Home with Private Dock close to Beach, Golf Tennis, BOAT OPTIONAL

Little Neck Bay

Eric S.

HK$8,137 total

includes taxes & fees

30 Oct - 31 Oct

A modern kitchen with white cabinetry, a central island, skylights, and a view of the outdoors.

19. Recently renovated 3 bedroom

Falmouth

Rosemary P.

HK$9,656 total

includes taxes & fees

14 Oct - 15 Oct

A covered porch with wicker furniture, a potted plant, and a view of a street.

20. Cape Cod Hyannis Rendezvous'

Barnstable

Daniel m.

HK$7,304 total

includes taxes & fees

11 Oct - 12 Oct

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Top Osterville Hotel Reviews

Sea Crest Beach Resort

10/10 Excellent

"it was my first time in cape cod and I picked this hotel because it had rooms right on the water, it was on my bucket list, I was absolutely not disappointed in any way, it was absolutely beautiful, i already am going to make plans to stay there again"

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