Book Holiday Homes in Osterville

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Featured Holiday Homes in Osterville

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 MA
The price is AU$542 per night from 17 May to 18 May
AU$542
17 May - 18 May
includes taxes & fees
With a stay at this vacation home in Plymouth, you'll be by the ocean, within a 15-minute drive of Cape Cod Beaches and Manomet Beach.
Opens in a new windowPlymouth private ocean front oversized suite on the bluff of Cape Cod Bay
Private Sandy Beach, Truly Oceanfront,Private Decks, Free Kayak, Sleeps  5

Private Sandy Beach, Truly Oceanfront,Private Decks, Free Kayak, Sleeps 5

South Yarmouth MA
With a stay at this vacation home in South Yarmouth (Bass River), you'll be a 1-minute drive from Cape Cod Beaches and 6 minutes from Main Street Hyannis.
Opens in a new windowPrivate Sandy Beach, Truly Oceanfront,Private Decks, Free Kayak, Sleeps 5
Charming 3 bed room with magnificent views & large deck

Charming 3 bed room with magnificent views & large deck

Barnstable MA
The price is AU$574 per night from 17 May to 18 May
AU$574
17 May - 18 May
includes taxes & fees
With a stay at this vacation home in Hyannis, you'll be within a 15-minute walk of Cape Cod Beaches and Hyannis Harbor.
Opens in a new windowCharming 3 bed room with magnificent views & large deck
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Steps to the Beach in East Falmouth, PET FRIENDLY &  clubhouse heated pool.

Steps to the Beach in East Falmouth, PET FRIENDLY & clubhouse heated pool.

East Falmouth MA
With a stay at this vacation home in East Falmouth, you'll be by the sea, a short 4-minute walk from Cape Cod Beaches and within 2 minutes by car from Waquoit ...
Opens in a new windowSteps to the Beach in East Falmouth, PET FRIENDLY & clubhouse heated pool.
Spacious Waterview Home - Spa, Pool Table & Fireplaces – for Families & Reunion

Spacious Waterview Home - Spa, Pool Table & Fireplaces – for Families & Reunion

Bourne MA
With a stay at this vacation home in Bourne, you'll be by the sea, within a 5-minute drive of Cape Cod Beaches and National Marine Life Center.
Opens in a new windowSpacious Waterview Home - Spa, Pool Table & Fireplaces – for Families & Reunion
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 MA
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 Main Street Hyannis.
Opens in a new window2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill
Lake House in Centerville with Private Water Access!

Lake House in Centerville with Private Water Access!

Barnstable MA
When you stay at this vacation home in Centerville, you'll be by the sea, within a 10-minute drive of Cape Cod Beaches and Main Street Hyannis.
Opens in a new windowLake House in Centerville with Private Water Access!
Mid-Cape Cod Luxury Escape!!

Mid-Cape Cod Luxury Escape!!

Yarmouth MA
With a stay at this vacation home in South Yarmouth (Bass River), you'll be within a 10-minute drive of Main Street Hyannis and Cape Cod Beaches.
Opens in a new windowMid-Cape Cod Luxury Escape!!
CLEAN, Walk To Beach, Ferries, Downtown, Newly Renovated House, Pet Friendly

CLEAN, Walk To Beach, Ferries, Downtown, Newly Renovated House, Pet Friendly

Yarmouth MA
A stay at this vacation home places you in the heart of Hyannis, within a 10-minute walk of Cape Cod Beaches and Main Street Hyannis.
Opens in a new windowCLEAN, Walk To Beach, Ferries, Downtown, Newly Renovated House, Pet Friendly
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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
2842 Holiday Homes
Lowest Price
AU$171
Highest Price
AU$574
Popular accommodation
Plymouth private ocean front oversized suite on the bluff of Cape Cod Bay, Private Sandy Beach, Truly Oceanfront,Private Decks, Free Kayak, Sleeps 5, Charming 3 bed room with magnificent views & large deck, Steps to the Beach in East Falmouth, PET FRIENDLY & clubhouse heated pool. , Spacious Waterview Home - Spa, Pool Table & Fireplaces – for Families & Reunion, 2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill, Lake House in Centerville with Private Water Access!, Mid-Cape Cod Luxury Escape!!, CLEAN, Walk To Beach, Ferries, Downtown, Newly Renovated House, Pet Friendly

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$310 per night from 17 May to 18 May
AU$310
17 May - 18 May
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.
Opens in a new windowMargaritaville Resort Cape Cod
Sea Crest Beach Resort

Sea Crest Beach Resort

3.5 out of 5
350 Quaker Rd North Falmouth MA
Fully refundableReserve now, pay when you stay
The price is AU$347 per night from 25 May to 26 May
AU$347
25 May - 26 May
includes taxes & fees
When you stay at Sea Crest Beach Resort in North Falmouth, you'll be near the bay, just steps from Cape Cod Beaches and Old Silver Beach.
Opens in a new windowSea Crest Beach Resort
Fairfield Inn & Suites by Marriott Cape Cod Hyannis

Fairfield Inn & Suites by Marriott Cape Cod Hyannis

3 out of 5
867 Iyannough Road Hyannis MA
Fully refundableReserve now, pay when you stay
The price is AU$171 per night from 26 May to 27 May
AU$171
26 May - 27 May
includes taxes & fees
With a stay at Fairfield Inn & Suites by Marriott Cape Cod Hyannis, you'll be centrally located in Hyannis, within a 5-minute drive of Main Street Hyannis and ...
Opens in a new windowFairfield Inn & Suites by Marriott Cape Cod Hyannis
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Iris Hotel Cape Cod

Iris Hotel Cape Cod

3 out of 5
291 Jones Rd Falmouth MA
Fully refundableReserve now, pay when you stay
The price is AU$192 per night from 17 May to 18 May
AU$192
17 May - 18 May
includes taxes & fees
When you stay at Iris Hotel Cape Cod in Falmouth, you'll be on a lake, within a 5-minute drive of Island Queen Ferry and Shining Sea Bikeway.
Opens in a new windowIris Hotel Cape Cod
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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.