Holiday Homes in Osterville

  • 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

In two weeks
19 Jun - 21 Jun
In two months
31 Jul - 2 Aug
In three months
28 Aug - 30 Aug
In four months
25 Sept - 27 Sept

Our top choices for Osterville holiday homes

Fridge, microwave, oven, stovetop

Cozy Riverfront Stay in Wareham

Cozy Riverfront Stay in Wareham
Wareham
10.0 out of 10, Exceptional, (3 reviews)
"Perfect for wedding guests. Spacious, clean and great viewWould definitely stay again"
United States
Karleen L.
The price is NZ$697
includes taxes & fees
3 June - 4 June
Cozy Riverfront Stay in Wareham
Sun-loungers, beach towels

Make this charming, modern retreat your home away from home!!

Make this charming, modern retreat your home away from home!!
Wareham
9.8 out of 10, Exceptional, (8 reviews)
"Great place! Great host!"
United States
Moira C.
The price is NZ$515
includes taxes & fees
4 June - 5 June
Make this charming, modern retreat your home away from home!!
Exterior

Ocean View Room @ Beach Resort / Habitat *HOT TUB*

Ocean View Room @ Beach Resort / Habitat *HOT TUB*
Cape Cod
The price is NZ$505
includes taxes & fees
7 June - 8 June
Ocean View Room @ Beach Resort / Habitat *HOT TUB*
Outdoor dining

Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail

Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail
West Brewster
9.6 out of 10, Exceptional, (51 reviews)
"We loved the house. Simple and comfortable, exactly what we needed to relax. thank you."
United States
Michael M.
The price is NZ$1,073
includes taxes & fees
4 June - 5 June
Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail
Terrace/patio

Plymouth private ocean front oversized suite on the bluff of Cape Cod Bay

Plymouth private ocean front oversized suite on the bluff of Cape Cod Bay
Plymouth
10.0 out of 10, Exceptional, (136 reviews)
"Beautiful room and view, hosts were communicative and check in/out were easy. Would definitely stay here again!"
United States
Alexander L.
The price is NZ$636
includes taxes & fees
14 June - 15 June
Plymouth private ocean front oversized suite on the bluff of Cape Cod Bay
Property grounds

Cottage Oasis by Lake with Kayaks, Fire Pit & a Huge Yard

Cottage Oasis by Lake with Kayaks, Fire Pit & a Huge Yard
Dennis
9.0 out of 10, Wonderful, (4 reviews)
"We enjoyed this Cape Cottage, centrally located in mid-cape. Clean with comfortable beds and host is very helpful. We will be back!"
United States
Linda P.
Cottage Oasis by Lake with Kayaks, Fire Pit & a Huge Yard
Exterior

Adorable Cape Escape W/ Private Beach Access, Full Kitchen, & Perfect Location

Adorable Cape Escape W/ Private Beach Access, Full Kitchen, & Perfect Location
Dennis Port
9.0 out of 10, Wonderful, (24 reviews)
"Loved this property. "
United States
Carol S.
The price is NZ$803
includes taxes & fees
3 June - 4 June
Adorable Cape Escape W/ Private Beach Access, Full Kitchen, & Perfect Location
Smart TV, books

Oldest Town of Cape Cod In The Historic District

Oldest Town of Cape Cod In The Historic District
Sandwich
9.0 out of 10, Wonderful, (19 reviews)
"We enjoyed our two night stay."
United States
Lonnie W.
The price is NZ$616
includes taxes & fees
3 June - 4 June
Oldest Town of Cape Cod In The Historic District
Dining

NEW - Cozy Cape Cod Family Getaway ~ A/C ~ SCREENED PORCH

NEW - Cozy Cape Cod Family Getaway ~ A/C ~ SCREENED PORCH
Dennis
10.0 out of 10, Exceptional, (11 reviews)
"Wonderful place! Thank you so much! "
United States
Jess W.
The price is NZ$979
includes taxes & fees
3 June - 4 June
NEW - Cozy Cape Cod Family Getaway ~ A/C ~ SCREENED PORCH
Smart TV, ping pong, books

Newly Renovated Hyannis Home w/ Fire Pit & Yard

Newly Renovated Hyannis Home w/ Fire Pit & Yard
Hyannis
10.0 out of 10, Exceptional, (2 reviews)
"Really enjoyed our stay. Very clean and comfortable home. The communication with the owners was excellent. We would definitely visit again. "
United States
Shawn B.
The price is NZ$950
includes taxes & fees
3 June - 4 June
Newly Renovated Hyannis Home w/ Fire Pit & Yard
Pool

Cozy Large Home in Harwich with Patio near Wequassett Resort

Cozy Large Home in Harwich with Patio near Wequassett Resort
Harwich
9.8 out of 10, Exceptional, (12 reviews)
"Host was very responsive and the house provided everything we needed. Great location! "
United States
Ashley M.
The price is NZ$812
includes taxes & fees
3 June - 4 June
Cozy Large Home in Harwich with Patio near Wequassett Resort
Exterior

Mermaid House @ The Compound Beach Resort Habitat

Mermaid House @ The Compound Beach Resort Habitat
Cape Cod
8.4 out of 10, Very good, (8 reviews)
"Love the place but felt like would of been better if the owner wasn’t around not that they where bad or annoying just didn’t feel like we was like away felt like we was being watched but besides that loved it Wish barbecue was working and speaker in house was weird set up but besides that it was amazing"
United States
Oscar B.
The price is NZ$1,274
includes taxes & fees
7 June - 8 June
Mermaid House @ The Compound Beach Resort Habitat
Outdoor dining

Family-friendly house w/gas grill, deck, streaming services - near Haigis Beach

Family-friendly house w/gas grill, deck, streaming services - near Haigis Beach
Dennis Port
The price is NZ$855
includes taxes & fees
30 June - 1 July
Family-friendly house w/gas grill, deck, streaming services - near Haigis Beach
Dining

Cape Cod's "Beach Rose"

Cape Cod's "Beach Rose"
Dennis
10.0 out of 10, Exceptional, (12 reviews)
"Very clean, great place for kids!"
United States
Ruth
The price is NZ$374
includes taxes & fees
14 June - 15 June
Cape Cod's "Beach Rose"
Fridge, microwave, oven, stovetop

Come Enjoy Cape Cod! Charming 3-BR house in pleasant Falmouth

Come Enjoy Cape Cod! Charming 3-BR house in pleasant Falmouth
Falmouth
9.6 out of 10, Exceptional, (11 reviews)
"Really beautiful place with a lot of space and a very helpful host"
United States
Gokul K.
The price is NZ$1,378
includes taxes & fees
7 June - 8 June
Come Enjoy Cape Cod! Charming 3-BR house in pleasant Falmouth
Smart TV, fireplace

Coastal Haven in West Dennis

Coastal Haven in West Dennis
Dennis
10.0 out of 10, Exceptional, (3 reviews)
"This was a great place to stay and relax, just a short walk to the beach and quick drive to great restaurants and activities. Highly recommend!!"
United States
Melissa J.
The price is NZ$1,191
includes taxes & fees
3 June - 4 June
Coastal Haven in West Dennis
Interior

Bike to Beach: Centerville Home w/ Deck!

Bike to Beach: Centerville Home w/ Deck!
Centerville
9.6 out of 10, Exceptional, (19 reviews)
"The house was very clean, updated and comfortable. It suited our needs beautifully. Communication was great and check in was very easy. The location was very convenient and it was wonderful to have ample parking."
United States
Jeanne S.
The price is NZ$1,049
includes taxes & fees
7 June - 8 June
Bike to Beach: Centerville Home w/ Deck!
Exterior

Family Cottage Close to Beach!!

Family Cottage Close to Beach!!
Harwichport
9.8 out of 10, Exceptional, (75 reviews)
"Everything was exactly as described - they provided beach towels and chairs which we used - the property was perfect for our stay"
United States
John N.
The price is NZ$1,324
includes taxes & fees
3 June - 4 June
Family Cottage Close to Beach!!
Beach

Contemporary coastal retreat nearby Falmouth beaches! w/ spacious living area

Contemporary coastal retreat nearby Falmouth beaches! w/ spacious living area
Falmouth
10.0 out of 10, Exceptional, (9 reviews)
"A beautiful home conveniently located-very clean Nd comfortable for 6 long time friends."
United States
Linda W.
The price is NZ$1,105
includes taxes & fees
21 June - 22 June
Contemporary coastal retreat nearby Falmouth beaches! w/ spacious living area
Smart TV, books

Cape Cod Farmhouse 1800s Charm

Cape Cod Farmhouse 1800s Charm
Dennis
The price is NZ$1,406
includes taxes & fees
8 June - 9 June
Cape Cod Farmhouse 1800s Charm
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
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
"The staff were absolutely wonderful!! Immaculate property... Nice pool and hot tub with a great breakfast!"
Jennifer 1-night trip
Posted 1 hour ago
Hyannis Travel Inn

Find out more about Osterville

Osterville Holiday Homes information

Number of reviews
321
Accommodation
2900 Holiday Homes
Lowest Price
NZ$374
Highest Price
NZ$1,406