A house by a lake with boats.

Holiday Homes in Osterville

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

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

Beach pass included • Modern 3BR Osterville retreat, walkable to village center
Osterville
10.0 out of 10, Exceptional, (24 reviews)
"Very comfortable, close to town, all around great stay."
United States
Elizabeth C.
The price is NZ$1,574
includes taxes & fees
22 Oct - 23 Oct
Beach pass included • Modern 3BR Osterville retreat, walkable to village center
A sandy beach with a calm lake and a forested hill in the background.

2. Charming 3-bedroom house in lovely Barnstable

Charming 3-bedroom house in lovely Barnstable
Barnstable
9.6 out of 10, Exceptional, (5 reviews)
"Excellent stay! Loved the home! "
United States
Cailee B.
The price is NZ$1,034
includes taxes & fees
18 Nov - 19 Nov
Charming 3-bedroom house in lovely Barnstable
A wide sandy beach with footprints leading to the water, a clear sky, and distant buildings.

3. 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 NZ$825
includes taxes & fees
22 Oct - 23 Oct
Cozy Spacious Home Walk to the Beach & 1 Mile to Downtown Hyannis
Private kitchen

4. Entire Hyannis Home - Near Downtown & Beaches

Entire Hyannis Home - Near Downtown & Beaches
Barnstable
8.8 out of 10, Excellent, (3 reviews)
"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...
United States
Bethany P.
The price is NZ$790
includes taxes & fees
5 Nov - 6 Nov
Entire Hyannis Home - Near Downtown & Beaches
A modern kitchen with a large island, stainless steel appliances, and grey cabinetry.

5. 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"
United States
steven c.
The price is NZ$1,681
includes taxes & fees
22 Oct - 23 Oct
New construction! Craigville Beach, Main St, Playground, Ice cream/restaurants!!
A beach with clear blue water and a sandy shore.

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

Cape Diem ; All new; 1.5m to Criagville, Hyannis beach; with WiFi, AC
Barnstable
10.0 out of 10, Exceptional, (7 reviews)
"Very nice property in a quiet and convenient location. Private backyard with outdoor shower. Interior was completely updated with very nice furnishings and appliances. All in all a great home that we will definitely return to. "
United States
Jim C.
The price is NZ$1,136
includes taxes & fees
22 Oct - 23 Oct
Cape Diem ; All new; 1.5m to Criagville, Hyannis beach; with WiFi, AC
A kitchen with a central island, white cabinets, a gas stove, and a sink.

7. 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 NZ$1,899
includes taxes & fees
9 Nov - 10 Nov
Spacious Lake House for Large Groups w Private Acre+ short path to Lake
A wooden deck with a table and chairs, overlooking a body of water and trees.

8. 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 NZ$1,935
includes taxes & fees
3 Nov - 4 Nov
Lakefront Stunning Cape Cod Views w Private Lake Beach - Backyard is the Lake !
A boat docked at a concrete pier with a sandy shore in the background.

9. 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 NZ$741
includes taxes & fees
22 Oct - 23 Oct
Private Waterfront, Beach, Dock, Kayaks, Paddle Boards and Hot Tub!
A garden pathway leading to a house with a stone wall and a wooden gate.

10. 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 NZ$1,088
includes taxes & fees
29 Oct - 30 Oct
Beach Pass Included!
A wooden deck with a wooden bench, a railing, and a window.

11. Hyannis Hideaway in Cape Cod

Hyannis Hideaway in Cape Cod
Barnstable
9.8 out of 10, Exceptional, (11 reviews)
"Awesome private property, close to Main Street and Craigsville beach. My friends and I stay in Hyannis every 4th of July and this home was super accommodating for groups and close to everything. Great stay would recommend. "
United States
Hunter W.
The price is NZ$1,457
includes taxes & fees
25 Oct - 26 Oct
Hyannis Hideaway in Cape Cod
A beach with sand, flowers, and a clear sky.

12. Sal's Place

Sal's Place
2.0 star property
Hyannis
The price is NZ$1,179
includes taxes & fees
26 Oct - 27 Oct
Sal's Place
A marina with boats docked, a wooden walkway, and a clear blue sky.

13. 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 NZ$1,577
includes taxes & fees
2 Nov - 3 Nov
Hyannis with Waterview [3bd]
A beach with clear water and a sandy shore.

14. 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 NZ$1,787
includes taxes & fees
30 Oct - 31 Oct
New Seabury Home with Private Dock close to Beach, Golf Tennis, BOAT OPTIONAL
A bedroom with a bed, nightstands, a window with a view, and a red curtain.

15. Walk to beaches & ferries ★ Snow's Creek Waterview

Walk to beaches & ferries ★ Snow's Creek Waterview
Barnstable
10.0 out of 10, Exceptional, (11 reviews)
"We thoroughly enjoyed our time at this property. There were 11 adults/teens across 3 families. Easy access to the beach and downtown. It really was perfect! I would stay again in a heartbeat."
United States
Jessica H.
The price is NZ$2,118
includes taxes & fees
2 Nov - 3 Nov
Walk to beaches & ferries ★ Snow's Creek Waterview
A spacious kitchen with a large island, wooden flooring, and a dining area with chairs and a table.

16. 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, (18 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 NZ$1,601
includes taxes & fees
21 Nov - 22 Nov
Spacious 4BR Cape Escape! Modern Tranquil house close to town, beaches, shops
A covered porch with wicker furniture, a potted plant, and a view of a street.

17. Cape Cod Hyannis Rendezvous'

Cape Cod Hyannis Rendezvous'
Barnstable
10.0 out of 10, Exceptional, (18 reviews)
"Great location"
United States
Sarah W.
The price is NZ$1,605
includes taxes & fees
22 Oct - 23 Oct
Cape Cod Hyannis Rendezvous'
A beach with a concrete walkway and wooden benches.

18. Charming House by the Beach with Patio, Grill, FirePit

Charming House by the Beach with Patio, Grill, FirePit
Bass River
10.0 out of 10, Exceptional, (14 reviews)
"This home was perfect for our family beach trip. There are several nearby beaches and restaurants. We loved being able to walk to the Skipper! The host was very responsive and the check in and check out processes were very clear. We all very much enjoyed our stay here!"
United States
Suzanne Q.
The price is NZ$926
includes taxes & fees
28 Oct - 29 Oct
Charming House by the Beach with Patio, Grill, FirePit
An outdoor patio with a wooden deck, wicker furniture, and a large umbrella.

19. 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)
"Loved the sleeping accommodations in the downstairs. All my seven grandchildren were able to sleep together and had a great time. Also, the pool was beautiful."
United States
james
The price is NZ$2,677
includes taxes & fees
18 Nov - 19 Nov
Summers by the Pool - Barnstable Village, Cape Cod, MA Home w/Pool + Beach Pass!
A cozy living room with a sofa, a chair, a television, and a fireplace.

20. Charming Family-Friendly Getaway in Sandwich!

Charming Family-Friendly Getaway in Sandwich!
Sandwich
The price is NZ$748
includes taxes & fees
22 Oct - 23 Oct
Charming Family-Friendly Getaway in Sandwich!
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.
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Top Osterville Hotel Reviews

Hyannis Harbor Hotel

Hyannis Harbor Hotel

10/10 Excellent
"Great location, staff was extremely helpful"
N. 1-night trip
Posted 2 hours ago
Hyannis Harbor Hotel

Find out more about Osterville

Osterville Holiday Homes information

Number of reviews
189
Accommodation
2963 Holiday Homes
Lowest Price
NZ$741
Highest Price
NZ$2,677