Book Holiday Homes in Osterville

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Featured Holiday Homes in Osterville

Coastal Cape Cod 3 bedroom home close to the beach, bike path and ponds!

Coastal Cape Cod 3 bedroom home close to the beach, bike path and ponds!

2 out of 5
Brewster
The price is NZ$1,224 per night from 1 Dec to 2 Dec
NZ$1,224
includes taxes & fees
1 Dec - 2 Dec
Stay at this vacation home in Brewster. Enjoy a garden, an in-room coffeemaker, and air conditioning. Popular attractions Sheep Pond and Cape Cod Museum of Natural ...
Coastal Cape Cod 3 bedroom home close to the beach, bike path and ponds!
4BR Ocean Timberland - Osterville  w/ private pool

4BR Ocean Timberland - Osterville w/ private pool

Barnstable
Stay at this vacation home in Osterville. Enjoy private pools, a pool table, and balconies. Popular attractions Hyannis Harbor and Stand Up & Paddle Cape Cod ...
4BR Ocean Timberland - Osterville w/ private pool
Coastal chic meets French Provençal in this newly renovated oceanfront home.

Coastal chic meets French Provençal in this newly renovated oceanfront home.

East Falmouth
The price is NZ$1,987 per night from 13 Dec to 14 Dec
NZ$1,987
includes taxes & fees
13 Dec - 14 Dec
Book a stay at this family-friendly vacation home in East Falmouth. Enjoy free WiFi, a beach locale, and a garden. Popular attractions Woods Hole Ferry Terminal ...
Coastal chic meets French Provençal in this newly renovated oceanfront home.
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2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill

2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill

Dennis
Stay at this vacation home in Dennis Port. Enjoy free WiFi, a water park, and balconies or patios. Popular attractions Cape Cod Theatre Company – Home of the ...
2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill
Cozy Cape home with outdoor shower and deck - minutes to beach

Cozy Cape home with outdoor shower and deck - minutes to beach

Barnstable
Book a stay at this family-friendly vacation home in Hyannis. Enjoy a water park, a garden, and patios. Popular attractions Hyannis Harbor and Cape Cod Melody ...
Cozy Cape home with outdoor shower and deck - minutes to beach
Charming cottage with deck, yard, & AC - walk to beach, Main Street, & ferry

Charming cottage with deck, yard, & AC - walk to beach, Main Street, & ferry

Falmouth
Stay at this vacation home in Falmouth. Enjoy a garden, patios, and cable/satellite TV service. Popular attractions Woods Hole Ferry Terminal and Island Queen ...
Charming cottage with deck, yard, & AC - walk to beach, Main Street, & ferry
Heart of Brewster .5 Miles to Beach!

Heart of Brewster .5 Miles to Beach!

Brewster
Stay at this vacation home in Brewster. Enjoy a garden, cable/satellite TV service, and an in-room coffeemaker. Popular attractions Brewster Ladies' Library ...
Heart of Brewster .5 Miles to Beach!
WATERFRONT w/Kayaks & SUP’s ★ Pet friendly ★ HOT TUB★Firepit & FPL★Deck & Patio

WATERFRONT w/Kayaks & SUP’s ★ Pet friendly ★ HOT TUB★Firepit & FPL★Deck & Patio

Yarmouth
Book a stay at this beach vacation home in South Yarmouth. Enjoy free WiFi, a beach locale, and a water park. Popular attractions Hyannis Harbor and Cultural ...
WATERFRONT w/Kayaks & SUP’s ★ Pet friendly ★ HOT TUB★Firepit & FPL★Deck & Patio
Oceanfront Home with Deck + Cape Cod Bay views!

Oceanfront Home with Deck + Cape Cod Bay views!

Sandwich
Book a stay at this beach vacation home in Sandwich. Enjoy a beach locale, a garden, and patios. Popular attractions Town Neck Beach and Town Beach are located ...
Oceanfront Home with Deck + Cape Cod Bay views!
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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.

Osterville Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Osterville vacation homes are the perfect way for you to wing it.

Holiday houses in Osterville let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Osterville in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Osterville adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Osterville with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Osterville vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Osterville Holiday Homes essential information

Accommodation
2552 Holiday Homes
Lowest Price
NZ$134
Highest Price
NZ$1,987
Popular accommodation
Coastal Cape Cod 3 bedroom home close to the beach, bike path and ponds!, 4BR Ocean Timberland - Osterville w/ private pool, Coastal chic meets French Provençal in this newly renovated oceanfront home. , 2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill, Cozy Cape home with outdoor shower and deck - minutes to beach, Charming cottage with deck, yard, & AC - walk to beach, Main Street, & ferry, Heart of Brewster .5 Miles to Beach!, WATERFRONT w/Kayaks & SUP’s ★ Pet friendly ★ HOT TUB★Firepit & FPL★Deck & Patio , Oceanfront Home with Deck + Cape Cod Bay views!

Top trending hotels in Osterville

Cape Sands Inn

Cape Sands Inn

2.5 out of 5
149 Main St - RT 28, West Yarmouth, MA
Fully refundableReserve now, pay when you stay
The price is NZ$134 per night from 23 Nov to 24 Nov
NZ$134
includes taxes & fees
23 Nov - 24 Nov
Book a stay at this family-friendly motel in West Yarmouth. Enjoy free parking, an outdoor pool, and a sauna. Our guests praise the pool and the helpful staff ...
Cape Sands Inn
Bayside Resort Hotel

Bayside Resort Hotel

3 out of 5
225 Route 28, West Yarmouth, MA
Fully refundableReserve now, pay when you stay
The price is NZ$156 per night from 8 Dec to 9 Dec
NZ$156
includes taxes & fees
8 Dec - 9 Dec
Stay at this 3-star beach hotel in West Yarmouth. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. ...
Bayside Resort Hotel
Holiday Inn Cape Cod-Falmouth, an IHG Hotel

Holiday Inn Cape Cod-Falmouth, an IHG Hotel

3 out of 5
291 Jones Rd, Falmouth, MA
Fully refundable
The price is NZ$176 per night from 5 Dec to 6 Dec
NZ$176
includes taxes & fees
5 Dec - 6 Dec
Stay at this 3-star business-friendly hotel in Falmouth. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions Woods Hole Ferry Terminal ...
Holiday Inn Cape Cod-Falmouth, an IHG Hotel
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Aiden by Best Western Cape Cod - West Yarmouth

Aiden by Best Western Cape Cod - West Yarmouth

3 out of 5
476 Route 28, West Yarmouth, MA
Fully refundableReserve now, pay when you stay
The price is NZ$197 per night from 1 Dec to 2 Dec
NZ$197
includes taxes & fees
1 Dec - 2 Dec
Stay at this 3-star business-friendly hotel in West Yarmouth. Enjoy free parking, an outdoor pool, and breakfast (surcharge). Our guests praise the helpful staff ...
Aiden by Best Western Cape Cod - West Yarmouth
Don't see what you're looking for?
See all available properties in Osterville
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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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.