Book Holiday Homes in Osterville

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Featured Holiday Homes in Osterville

Newly Renovated Near Amazing Sunset Beach

Newly Renovated Near Amazing Sunset Beach

Falmouth MA
Stay at this holiday home in North Falmouth. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Cataumet Arts Center and Handy Point are ...
Opens in a new windowNewly Renovated Near Amazing Sunset Beach
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
Stay at this holiday home in Dennis Port. Enjoy free Wi-Fi, a water park and laundry facilities. Popular attractions Cape Cod Theatre Company – Home of the Harwich ...
Opens in a new window2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill
Cape Getaway 4 Bedroom w/ Outdoor Shower, Ramp Access to Water, New Bathroom

Cape Getaway 4 Bedroom w/ Outdoor Shower, Ramp Access to Water, New Bathroom

Falmouth MA
Stay at this family-friendly holiday home in East Falmouth. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Waquoit Bay National Estuarine ...
Opens in a new windowCape Getaway 4 Bedroom w/ Outdoor Shower, Ramp Access to Water, New Bathroom
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Moon Compass Escape – Spacious Cape Cod Retreat

Moon Compass Escape – Spacious Cape Cod Retreat

Sandwich MA
Stay at this holiday home in Sandwich. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Lowell Holly and Mashpee Wampanoag Indian Museum ...
Opens in a new windowMoon Compass Escape – Spacious Cape Cod Retreat
Beach front, fenced yard, dogs welcome, central air, fire pit, 3 kayaks, hot tub

Beach front, fenced yard, dogs welcome, central air, fire pit, 3 kayaks, hot tub

East Falmouth MA
Stay at this beach holiday home in East Falmouth. Enjoy free Wi-Fi, a beach locale and a garden. Popular attractions Falmouth Country Club and Cape Cod Winery ...
Opens in a new windowBeach front, fenced yard, dogs welcome, central air, fire pit, 3 kayaks, hot tub
Falmouth Cape - Walk to Island Queen ferry to Martha's Vineyard, Beach, Downtown

Falmouth Cape - Walk to Island Queen ferry to Martha's Vineyard, Beach, Downtown

Falmouth MA
Stay at this holiday home in Falmouth. Enjoy free Wi-Fi, a garden and laundry facilities. Our guests praise the helpful staff in their reviews. Popular attractions ...
Opens in a new windowFalmouth Cape - Walk to Island Queen ferry to Martha's Vineyard, Beach, Downtown
Completely Renovated Cottage Overlooking Nantucket Sound with Private Beach

Completely Renovated Cottage Overlooking Nantucket Sound with Private Beach

Dennis MA
Stay at this beach holiday home in Dennis Port. Enjoy free Wi-Fi, a beach locale and a garden. Popular attractions Sea Street Beach and Haigis Beach are located ...
Opens in a new windowCompletely Renovated Cottage Overlooking Nantucket Sound with Private Beach
WATERFRONT Kayaks & SUP’s ★ Pet friendly ★ HOT TUB ★ Firepit & FPL★ King bed

WATERFRONT Kayaks & SUP’s ★ Pet friendly ★ HOT TUB ★ Firepit & FPL★ King bed

Yarmouth MA
Stay at this beach holiday home in South Yarmouth. Enjoy free Wi-Fi, a beach locale and a water park. Popular attractions Captain Bangs Hallett House and Bass ...
Opens in a new windowWATERFRONT Kayaks & SUP’s ★ Pet friendly ★ HOT TUB ★ Firepit & FPL★ King bed
Falmouth Luxury Retreat -  Walk to Beaches -  Heated Pool - Near Wood's Hole

Falmouth Luxury Retreat - Walk to Beaches - Heated Pool - Near Wood's Hole

Falmouth MA
Stay at this family-friendly holiday home in Falmouth. Enjoy private pools, a garden and laundry facilities. Popular attractions Spohr Gardens and Quissett Harbor ...
Opens in a new windowFalmouth Luxury Retreat - Walk to Beaches - Heated Pool - Near Wood's Hole
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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
2955 Holiday Homes
Lowest Price
NZ$148
Highest Price
NZ$333
Popular accommodation
Newly Renovated Near Amazing Sunset Beach, 2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill, Cape Getaway 4 Bedroom w/ Outdoor Shower, Ramp Access to Water, New Bathroom, Moon Compass Escape – Spacious Cape Cod Retreat, Beach front, fenced yard, dogs welcome, central air, fire pit, 3 kayaks, hot tub, Falmouth Cape - Walk to Island Queen ferry to Martha's Vineyard, Beach, Downtown, Completely Renovated Cottage Overlooking Nantucket Sound with Private Beach, WATERFRONT Kayaks & SUP’s ★ Pet friendly ★ HOT TUB ★ Firepit & FPL★ King bed, Falmouth Luxury Retreat - Walk to Beaches - Heated Pool - Near Wood's Hole

Top trending hotels in Osterville

Fairfield Inn & Suites by Marriott Cape Cod Hyannis

Fairfield Inn & Suites by Marriott Cape Cod Hyannis

2.5 out of 5
867 Iyannough Road Hyannis MA
Fully refundableReserve now, pay when you stay
The price is NZ$218 per night from 1 Jan to 2 Jan
NZ$218
1 Jan - 2 Jan 2026
includes taxes & fees
Stay at this business-friendly hotel in Hyannis. Enjoy free breakfast, free Wi-Fi and a fitness centre. Our guests praise the helpful staff in their reviews. ...
Opens in a new windowFairfield Inn & Suites by Marriott Cape Cod Hyannis
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$333 per night from 18 Dec to 19 Dec
NZ$333
18 Dec - 19 Dec
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
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 NZ$148 per night from 21 Dec to 22 Dec
NZ$148
21 Dec - 22 Dec
includes taxes & fees
Stay at this family-friendly motel in West Yarmouth. Enjoy free parking, an outdoor pool and a sauna. Our guests praise the pool and the helpful staff in their ...
Opens in a new windowCape Sands Inn
Save an average of 15% on thousands of hotels when you're signed in
Falmouth Inn

Falmouth Inn

2 out of 5
824 Main Street Falmouth MA
Fully refundableReserve now, pay when you stay
The price is NZ$250 per night from 28 Dec to 29 Dec
NZ$250
28 Dec - 29 Dec
includes taxes & fees
Stay at this business-friendly hotel in Falmouth. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff and the clean rooms ...
Opens in a new windowFalmouth Inn
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.