Book Holiday Homes in Osterville

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Featured Holiday Homes in Osterville

Charming updated bungalow with firepit, fast WiFi, & walkable locale near beach

Charming updated bungalow with firepit, fast WiFi, & walkable locale near beach

West Yarmouth
Stay at this vacation home in West Yarmouth. Enjoy a garden, patios, and an in-room coffeemaker. Popular attractions Cape Cod Inflatable Park and Hyannis Harbor ...
Charming updated bungalow with firepit, fast WiFi, & walkable locale near beach
3 Mi to Beach: Historic Farmhouse on Cape Cod!

3 Mi to Beach: Historic Farmhouse on Cape Cod!

South Dennis
Stay at this vacation home in South Dennis. Enjoy a garden, laundry facilities, and patios. Popular attractions Mayflower Beach and Jericho House and Barn Museum ...
3 Mi to Beach: Historic Farmhouse on Cape Cod!
Hyannis Hideaway in Cape Cod

Hyannis Hideaway in Cape Cod

Barnstable
The price is NZ$1,195 per night from 10 Sept to 11 Sept
NZ$1,195
10 Sept - 11 Sept
includes taxes & fees
Stay at this vacation home in Hyannis. Enjoy free WiFi and air conditioning. Popular attractions Hyannis Harbor and Cape Cod Melody Tent are located nearby.
Hyannis Hideaway in Cape Cod
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Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs

Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs

Oak Bluffs
Stay at this vacation home in Oak Bluffs. Enjoy laundry facilities, patios, and cable/satellite TV service. Popular attractions Inkwell Beach and Oak Bluffs ...
Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs
Cape Cod Getaway – 3BR Sandwich Home, Walk to Beach, AC & WiFi

Cape Cod Getaway – 3BR Sandwich Home, Walk to Beach, AC & WiFi

Sandwich
Stay at this vacation home in Sandwich. Enjoy a garden, laundry facilities, and patios. Popular attractions Sandwich Mini Golf and Historic Sandwich Village ...
Cape Cod Getaway – 3BR Sandwich Home, Walk to Beach, AC & WiFi
Ocean Breeze Motel - Standard Double

Ocean Breeze Motel - Standard Double

South Yarmouth
The price is NZ$344 per night from 10 Sept to 11 Sept
NZ$344
10 Sept - 11 Sept
includes taxes & fees
Stay at this motel in South Yarmouth. Enjoy free breakfast, tennis courts, and air conditioning. Our guests praise the helpful staff in our reviews. Popular ...
Ocean Breeze Motel - Standard Double
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 laundry facilities. Popular attractions Cape Cod Inflatable Park and Cape Cod Theatre ...
2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill
3-bedroom house in charming Dennis minutes to Corporation Beach. Relax & unwind.

3-bedroom house in charming Dennis minutes to Corporation Beach. Relax & unwind.

Dennis
Stay at this vacation home in Dennis. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Mayflower Beach and Corporation Beach are located ...
3-bedroom house in charming Dennis minutes to Corporation Beach. Relax & unwind.
Charming coastal home near pond with sunroom, open layout, yard & AC

Charming coastal home near pond with sunroom, open layout, yard & AC

Yarmouth
Stay at this property in South Yarmouth. Enjoy a garden, laundry facilities, and patios. Popular attractions Cape Cod Inflatable Park and Hyannis Harbor are ...
Charming coastal home near pond with sunroom, open layout, yard & AC
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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
3199 Holiday Homes
Lowest Price
NZ$176
Highest Price
NZ$1,195
Popular accommodation
Charming updated bungalow with firepit, fast WiFi, & walkable locale near beach, 3 Mi to Beach: Historic Farmhouse on Cape Cod!, Hyannis Hideaway in Cape Cod, Tranquil Home with Private Deck - Walk to Beaches and Downtown Oak Bluffs, Cape Cod Getaway – 3BR Sandwich Home, Walk to Beach, AC & WiFi, Ocean Breeze Motel - Standard Double, 2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill, 3-bedroom house in charming Dennis minutes to Corporation Beach. Relax & unwind., Charming coastal home near pond with sunroom, open layout, yard & AC

Top trending hotels in Osterville

Margaritaville Resort Cape Cod

Margaritaville Resort Cape Cod

4 out of 5
1225 Iyannough Rd, Hyannis, MA
Fully refundableReserve now, pay when you stay
The price is NZ$448 per night from 1 Sept to 2 Sept
NZ$448
1 Sept - 2 Sept
includes taxes & fees
Stay at this 4-star spa resort in Hyannis. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the clean rooms in our reviews. Popular attractions ...
Margaritaville Resort Cape Cod
Hyannis Plaza Hotel

Hyannis Plaza Hotel

2.5 out of 5
662 Main Street, Hyannis, MA
Fully refundableReserve now, pay when you stay
The price is NZ$176 per night from 9 Sept to 10 Sept
NZ$176
9 Sept - 10 Sept
includes taxes & fees
Book a stay at this luxury hotel in Hyannis. Enjoy free parking, an outdoor pool, and a 24-hour front desk. Popular attractions Hyannis Harbor and Cape Codder ...
Hyannis Plaza Hotel
Falmouth Inn

Falmouth Inn

2 out of 5
824 Main Street, Route 28, Falmouth, MA
Fully refundableReserve now, pay when you stay
The price is NZ$286 per night from 2 Sept to 3 Sept
NZ$286
2 Sept - 3 Sept
includes taxes & fees
Book a stay at this business-friendly hotel in Falmouth. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Falmouth Inn
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Bayside Resort Hotel

Bayside Resort Hotel

3 out of 5
225 Route 28, West Yarmouth, MA
Fully refundableReserve now, pay when you stay
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
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.