Holiday Homes in Osterville

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
28 Nov - 30 Nov
In two weeks
5 Dec - 7 Dec
In one month
19 Dec - 21 Dec
In two months
16 Jan - 18 Jan

Featured Holiday Homes in Osterville

Fridge, microwave, oven, stovetop
Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!

Holiday Home in West Brewster

2.0 star property
10.0 out of 10, Exceptional, (24)
"Beautiful, well appointed home ideally situated for exploring all the Cape has to offer from the Canal to Provincetown. Very enjoyable and relaxing vacation venue."
United States
Art T.
The price is AU$1,045
includes taxes & fees
9 Dec - 10 Dec
Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!
Beach
Cottage Oasis by Lake with Kayaks, Fire Pit & a Huge Yard

Holiday Home in Dennis

2.0 star property
9.0 out of 10, Wonderful, (2)
"Very cute cottage. Very clean and grounds well manicured. "
United States
Anonymous traveller
The price is AU$533
includes taxes & fees
30 Nov - 1 Dec
Cottage Oasis by Lake with Kayaks, Fire Pit & a Huge Yard
Outdoor dining
2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill

Holiday Home in Dennis

10.0 out of 10, Exceptional, (176)
"Excellent property, super clean and location is perfect! "
United States
Karen B.
The price is AU$489
includes taxes & fees
1 Dec - 2 Dec
2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill
Fridge, microwave, oven, stovetop
Make this charming, modern retreat your home away from home!!

Holiday Home in Wareham

9.6 out of 10, Exceptional, (5)
"Great stay. Clean, comfortable, and exactly as listed. Perfect location with a great backyard to grill or sit by the fire pit. Check-in was easy and the host was very responsive. Would definitely book again!!"
United States
Laura D.
The price is AU$486
includes taxes & fees
30 Nov - 1 Dec
Make this charming, modern retreat your home away from home!!
Marina
Beach, Breeze & Bunk Beds. FamilyFun Steps to the Shore. Dog-Friendly, GameWall.

Holiday Home in Wareham

10.0 out of 10, Exceptional, (5)
"This property is just as described, even better in person. Very cute and clean, with everything you could possibly need during your stay. Great location and very quiet neighborhood. Definitely recommend. "
United States
Dayna F.
Beach, Breeze & Bunk Beds. FamilyFun Steps to the Shore. Dog-Friendly, GameWall.
Beach nearby
Cozy Spacious Home Walk to the Beach & 1 Mile to Downtown Hyannis

Holiday Home in Barnstable

8.6 out of 10, Excellent, (8)
"This was an amazing property and our host was awesome and checked in to make sure everything was going well. Would definitely stay here again! Thank you! "
United States
Kim
The price is AU$813
includes taxes & fees
30 Nov - 1 Dec
Cozy Spacious Home Walk to the Beach & 1 Mile to Downtown Hyannis
Fridge, microwave, oven, stovetop
Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail

Holiday Home in West Brewster

9.6 out of 10, Exceptional, (50)
"House was perfect for our family reunion! "
United States
Gregg H.
The price is AU$811
includes taxes & fees
30 Nov - 1 Dec
Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail
Beach nearby
Charming House by the Beach with Patio, Grill, FirePit

Holiday Home in Bass River

9.8 out of 10, Exceptional, (7)
"What a tremendous location with a short 3 minute walk to Seaview Beach and a 5 minute walk to Skippers Clam House! The house has great sleeping capacity and has a great fire pit and outdoor seating area and a great outdoor shower with plenty of hot water for all! We will return in the future!"
United States
Neil M.
The price is AU$883
includes taxes & fees
25 Nov - 26 Nov
Charming House by the Beach with Patio, Grill, FirePit
Fridge, microwave, oven, stovetop
🔥BLACK FRIDAY🔥 40-Spacious,cozy, waterfront house in Yarmouth

Holiday Home in South Yarmouth

9.0 out of 10, Wonderful, (4)
"The house was immaculate. The property was picturesque. Neighborhood was stunning. We LOVED this home. "
United States
Mary R.
The price is AU$832
includes taxes & fees
25 Nov - 26 Nov
🔥BLACK FRIDAY🔥 40-Spacious,cozy, waterfront house in Yarmouth
Fridge, microwave, oven, stovetop
Oldest Town of Cape Cod In The Historic District

Holiday Home in Sandwich

9.0 out of 10, Wonderful, (17)
"The house was a great cozy place to stay. Ed was pleasant and offer tips on where to go and what to see. We had a great time. "
United States
Justin V.
The price is AU$615
includes taxes & fees
25 Nov - 26 Nov
Oldest Town of Cape Cod In The Historic District
Property grounds
Big Sandy Beachcomber

Holiday Home in Ponds of Plymouth

10.0 out of 10, Exceptional, (11)
"Our stay was perfect! The house was clean and the host very responsive throughout! Would definitely stay again!"
United States
Ben L.
The price is AU$770
includes taxes & fees
1 Dec - 2 Dec
Big Sandy Beachcomber
Fridge, microwave, oven, stovetop
Walk to the Beach - Modern Home w/ FirePit, Bikes, Office, Grill + More!

Holiday Home in Yarmouth

10.0 out of 10, Exceptional, (12)
"We rented this house for a family vacation and would without a doubt rent it again! Everything you can possibly need was at the house. If you needed anything additional the host was very responsive and there to assist. We loved the time we got to spend here together. "
United States
Cara B.
The price is AU$1,073
includes taxes & fees
30 Nov - 1 Dec
Walk to the Beach - Modern Home w/ FirePit, Bikes, Office, Grill + More!
Exterior
Cozy Large Home in Harwich with Patio near Wequassett Resort

Holiday Home in Harwich

9.8 out of 10, Exceptional, (11)
"Host was very responsive and the house provided everything we needed. Great location! "
United States
Ashley M.
The price is AU$817
includes taxes & fees
7 Dec - 8 Dec
Cozy Large Home in Harwich with Patio near Wequassett Resort
Exterior
WALK to the Beach + FirePit, Bikes, Paddleboards - Modern House

Holiday Home in Yarmouth

10.0 out of 10, Exceptional, (3)
"We only stayed one night, but wish we could have stayed longer. Host was responsive and property was in great shape."
United States
Jared W.
The price is AU$827
includes taxes & fees
30 Nov - 1 Dec
WALK to the Beach + FirePit, Bikes, Paddleboards - Modern House
Fridge, microwave, oven, stovetop
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach

Holiday Home in Falmouth

10.0 out of 10, Exceptional, (209)
"As always, lovely home. Perfect place."
United States
Sarah C.
The price is AU$776
includes taxes & fees
30 Nov - 1 Dec
Located Steps Away To Main Street And .7 Miles From Surf Drive Beach
Sun-loungers
Eazy Breezy Beach Home

Holiday Home in Dennis

10.0 out of 10, Exceptional, (2)
"A great place! Cute and clean with all the comforts of home...and more!"
United States
Kristen D.
The price is AU$574
includes taxes & fees
30 Nov - 1 Dec
Eazy Breezy Beach Home
Outdoor dining
Newly Renovated Martha's Vineyard Vacation Rental!

Holiday Home in Katama

9.6 out of 10, Exceptional, (47)
"Stay was nice, property is very clean and in close distance to most everything. Just wish they had made the lack of towels and linens more obvious in the listing. "
United States
James L.
The price is AU$950
includes taxes & fees
29 Nov - 30 Nov
Newly Renovated Martha's Vineyard Vacation Rental!
Fridge, microwave, oven, stovetop
Coastal Haven in West Dennis

Holiday Home in Dennis

2.0 star property
10.0 out of 10, Exceptional, (3)
"Overall the property was perfect. Great location, super clean and plenty of room for our family of 4. The only negative I can say is that the property is a duplex and that’s not mentioned in the listing. Overall great spot and would stay there again!"
United States
Edward R.
The price is AU$1,031
includes taxes & fees
25 Nov - 26 Nov
Coastal Haven in West Dennis
Interior
Gorgeous Home 1 mile to Beach, by Cape Cod Bikepath

Holiday Home in Dennis

The price is AU$867
includes taxes & fees
7 Dec - 8 Dec
Gorgeous Home 1 mile to Beach, by Cape Cod Bikepath
Property grounds
Modern & Comfy Family Oasis ~ Games, Backyard, BBQ

Holiday Home in Dennis

9.2 out of 10, Wonderful, (7)
"Five star because hosts were very responsive and truly went out of their way to make sure our stay was comfortable and enjoyable. Mid cape location is perfect for all the beaches we visit and biking we do. "
United States
Mark L.
The price is AU$908
includes taxes & fees
4 Dec - 5 Dec
Modern & Comfy Family Oasis ~ Games, Backyard, BBQ
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.
View all properties

Black Friday Sale

Save up to 40% on select hotels
Book now
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Osterville Hotel Reviews

Hyannis Travel Inn

Hyannis Travel Inn

10/10 Excellent
"Nice staff Clean room Comfortable bed Convenient location "
Teria 3-night trip
Posted 3 days ago
Hyannis Travel Inn

Find out more about Osterville

Osterville Holiday Homes information

Number of reviews
548
Accommodation
2990 Holiday Homes
Lowest Price
AU$486
Highest Price
AU$1,073

Explore a world of travel with Expedia