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
When you stay at this vacation home in West Yarmouth, you'll be by the sea, a 1-minute drive from Cape Cod Beaches and 7 minutes from 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
When you stay at this vacation home in South Dennis, you'll be by the sea, within a 15-minute drive of Cape Cod Beaches and Mayflower Beach.
3 Mi to Beach: Historic Farmhouse on Cape Cod!
Hyannis Hideaway in Cape Cod

Hyannis Hideaway in Cape Cod

Barnstable
The price is AU$1,080 per night from 8 Sept to 9 Sept
AU$1,080
8 Sept - 9 Sept
includes taxes & fees
With a stay at this vacation home in Hyannis, you'll be a 4-minute drive from Hyannis Harbor and 8 minutes from Cape Cod Beaches.
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
With a stay at this vacation home in Oak Bluffs, you'll be within a 10-minute drive of Inkwell Beach and Martha's Vineyard Hospital Development.
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
With a stay at this vacation home in Sandwich, you'll be within a 10-minute drive of Cape Cod Beaches and Sandwich Mini Golf.
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 AU$317 per night from 7 Sept to 8 Sept
AU$317
7 Sept - 8 Sept
includes taxes & fees
With a stay at this motel in South Yarmouth (Bass River), you'll be a 1-minute drive from Cape Cod Beaches and 8 minutes from Hyannis Harbor.
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
The price is AU$578 per night from 14 Aug to 15 Aug
AU$578
14 Aug - 15 Aug
includes taxes & fees
When you stay at this vacation home in Dennis Port, you'll be by the sea, within a 15-minute drive of Cape Cod Beaches and Mayflower Beach.
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
With a stay at this vacation home in Dennis, you'll be a 1-minute drive from Cape Cod Beaches and 5 minutes from Mayflower Beach.
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
When you stay at this property in South Yarmouth, you'll be by the sea, within a 10-minute drive of Cape Cod Beaches and Hyannis Harbor.
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
3215 Holiday Homes
Lowest Price
AU$160
Highest Price
AU$1,080
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 AU$409 per night from 1 Sept to 2 Sept
AU$409
1 Sept - 2 Sept
includes taxes & fees
Located in Hyannis, Margaritaville Resort Cape Cod is in a shopping district, a 4-minute drive from Cape Cod Melody Tent and 5 minutes from Hyannis Harbor.
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 AU$160 per night from 9 Sept to 10 Sept
AU$160
9 Sept - 10 Sept
includes taxes & fees
With a stay at Hyannis Plaza Hotel, you'll be centrally located in Hyannis, within a 5-minute drive of Hyannis Harbor and Cape Cod Beaches.
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 AU$261 per night from 2 Sept to 3 Sept
AU$261
2 Sept - 3 Sept
includes taxes & fees
With a stay at Falmouth Inn, you'll be centrally located in Falmouth, a 2-minute drive from Cape Cod Beaches and 10 minutes from Woods Hole Ferry Terminal.
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
When you stay at Bayside Resort Hotel in West Yarmouth, you'll be near the bay, within a 5-minute drive of Cape Cod Beaches and Hyannis Harbor.
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.