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$7,113 total

includes taxes & fees

13 Oct - 14 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

HK$8,772 total

includes taxes & fees

13 Oct - 14 Oct

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$5,119 total

includes taxes & fees

13 Oct - 14 Oct

A wide sandy beach with footprints leading to the water, a clear sky, and distant buildings.

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

Barnstable

Jen M.

HK$3,793 total

includes taxes & fees

8 Oct - 9 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

1 Nov - 2 Nov

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

8 Oct - 9 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$8,678 total

includes taxes & fees

27 Oct - 28 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$8,916 total

includes taxes & fees

27 Oct - 28 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$3,853 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

13 Oct - 14 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

8 Oct - 9 Oct

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

14. Hyannis with Waterview [3bd]

Barnstable

Eugene C.

HK$7,198 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$9,636 total

includes taxes & fees

8 Oct - 9 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$7,303 total

includes taxes & fees

8 Oct - 9 Oct

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Top Osterville Hotel Reviews

Iris Hotel Cape Cod

10/10 Excellent

"The Iris hotel was a good stay. I liked how the room smelled fresh, and the hallways smelled of new carpet. The bathroom was small and showed signs of being a little but it was manageable and the breakfast was great."

Uncommoner Hotel by Reverie Boutique Collection

10/10 Excellent

"The minute you walk into the check-in/lobby area, you have a definite sense of the vibe of this property. It's quirky and swanky without trying hard at all. Subtly cool and inviting. The employee who greeted us was warm and friendly. Although our room faced the road, it wasn't too much of a bother. The room was beautifully appointed and large. The pool was chilly, but on a warmer day it would have been so relaxing. The entire property is beautiful and well maintained. If we ever go to the Cape again, we will definitely book this hotel again. Gorgeous all around!"

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