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 NZ$656 per night from 20 May to 21 May
NZ$656
20 May - 21 May
includes taxes & fees
Stay at this holiday home in Plymouth. Enjoy free Wi-Fi, a garden and patios. Popular attractions Manomet Beach and Ellisville Harbor State Park are located ...
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
Stay at this beach holiday home in South Yarmouth. Enjoy free Wi-Fi, a beach locale and a garden. Popular attractions Hyannis Harbor and 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 NZ$713 per night from 18 May to 19 May
NZ$713
18 May - 19 May
includes taxes & fees
Stay at this holiday home in Hyannis. Enjoy free Wi-Fi, patios and air conditioning. Popular attractions Hyannis Harbor and Main Street Hyannis are located ...
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
Stay at this holiday home in East Falmouth. Enjoy a garden, laundry facilities and patios. Popular attractions Waquoit Bay National Estuarine Research Reserve ...
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
Stay at this family-friendly holiday home in Bourne. Enjoy free Wi-Fi, a sauna and a garden. Popular attractions National Marine Life Center and Aptucxet Trading ...
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
The price is NZ$487 per night from 19 May to 20 May
NZ$487
19 May - 20 May
includes taxes & fees
Stay at this holiday home in Dennis Port. Enjoy free Wi-Fi, laundry facilities and balconies or patios. Popular attractions Cape Cod Theatre Company – Home of ...
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
Stay at this holiday home in Centerville. Enjoy a garden, laundry facilities and an in-room coffee maker. Popular attractions Main Street Hyannis and 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
Stay at this holiday home in South Yarmouth. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Hyannis Harbor and Main Street Hyannis are ...
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
Stay at this family-friendly holiday home in Hyannis. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Hyannis Harbor 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
2960 Holiday Homes
Lowest Price
NZ$210
Highest Price
NZ$713
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 NZ$430 per night from 20 May to 21 May
NZ$430
20 May - 21 May
includes taxes & fees
Stay at this spa resort in Hyannis. Enjoy free Wi-Fi, free parking and a full-service spa. Our guests praise the clean rooms in their reviews. Popular attractions ...
Opens in a new windowMargaritaville Resort Cape Cod
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 NZ$210 per night from 26 May to 27 May
NZ$210
26 May - 27 May
includes taxes & fees
Stay at this business-friendly hotel in Hyannis. Enjoy free breakfast, free Wi-Fi and a 24-hour fitness centre. Our guests praise the helpful staff in their ...
Opens in a new windowFairfield Inn & Suites by Marriott Cape Cod Hyannis
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 NZ$425 per night from 25 May to 26 May
NZ$425
25 May - 26 May
includes taxes & fees
Stay at this beach hotel in North Falmouth. Enjoy free Wi-Fi, free parking and an outdoor pool. Our guests praise the helpful staff and the clean rooms in their ...
Opens in a new windowSea Crest Beach Resort
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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 NZ$255 per night from 18 May to 19 May
NZ$255
18 May - 19 May
includes taxes & fees
Stay at this business-friendly hotel in Falmouth. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Popular attractions Woods Hole Ferry Terminal and ...
Opens in a new windowIris Hotel Cape Cod
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.