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 AU$1,118 per night from 1 Dec to 2 Dec
AU$1,118
includes taxes & fees
1 Dec - 2 Dec
With a stay at this vacation home in Brewster (West Brewster), you'll be a 2-minute drive from Sheep Pond and 5 minutes from Rail Trail Bike Shop.
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
With a stay at this vacation home in Osterville, you'll be within a 10-minute drive of Stand Up & Paddle Cape Cod and Cotuit Center for the Arts.
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 AU$1,814 per night from 13 Dec to 14 Dec
AU$1,814
includes taxes & fees
13 Dec - 14 Dec
With a stay at this vacation home in East Falmouth, you'll be on the beach, just a 3-minute walk from Cape Cod Beaches and 5 minutes by foot from Menauhant ...
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
When you stay at this vacation home in Dennis Port, you'll be by the sea, within a 5-minute drive of Cape Cod Theatre Company – Home of the Harwich Jr. Theatre ...
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
When you stay at this vacation home in Hyannis, you'll be by the sea, within a 5-minute drive of Cape Cod Melody Tent and St. Francis Xavier Church.
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
With a stay at this vacation home in Falmouth (Falmouth Heights), you'll be within a 10-minute walk of Island Queen Ferry and Cape Cod Beaches.
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
Located in Brewster, this vacation home is by the sea, within a 15-minute walk of Cape Cod Beaches and Breakwater Beach.
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
With a stay at this vacation home in South Yarmouth (Bass River), you'll be within a 5-minute drive of Bass River Sports World and Cultural Center of Cape ...
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
When you stay at this vacation home in Sandwich, you'll be on the beach, within a 10-minute walk of Cape Cod Beaches and Town Beach.
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
AU$131
Highest Price
AU$1,814
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 AU$131 per night from 25 Nov to 26 Nov
AU$131
includes taxes & fees
25 Nov - 26 Nov
Located in West Yarmouth, Cape Sands Inn is near the bay, within a 5-minute drive of John F. Kennedy Hyannis Museum and Cape Cod Inflatable Park.
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 AU$141 per night from 8 Dec to 9 Dec
AU$141
includes taxes & fees
8 Dec - 9 Dec
With a stay at Bayside Resort Hotel in West Yarmouth, you'll be near the bay, just a 1-minute walk from Main Street and 8 minutes by foot from Putter's Paradise ...
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 AU$159 per night from 24 Nov to 25 Nov
AU$159
includes taxes & fees
24 Nov - 25 Nov
When you stay at Holiday Inn Cape Cod-Falmouth, an IHG Hotel in Falmouth, you'll be on a lake, within a 5-minute drive of Island Queen Ferry and Cape Cod ...
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 AU$178 per night from 1 Dec to 2 Dec
AU$178
includes taxes & fees
1 Dec - 2 Dec
When you stay at Aiden by Best Western Cape Cod - West Yarmouth in West Yarmouth, you'll be near the beach, within a 5-minute drive of John F. Kennedy Hyannis ...
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.

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^Subject to availability and chosen travel dates.