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
With a stay at this vacation home in North Falmouth, you'll be within a 5-minute drive of Cape Cod Beaches and Cataumet Arts Center.
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
The price is AU$475 per night from 28 Dec to 29 Dec
AU$475
28 Dec - 29 Dec
includes taxes & fees
With a stay at this vacation home in Dennis Port, you'll be by the sea, within a 5-minute drive of Cape Cod Beaches and Cape Cod Theatre Company – Home of the ...
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
With a stay at this vacation home, you'll be centrally located in East Falmouth, within a 5-minute drive of Cape Cod Beaches and 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
Located in Sandwich, this vacation home is by the sea, a 3-minute drive from Santuit Pond and 6 minutes from 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
With a stay at this vacation home in East Falmouth, you'll be on the beach, within a 15-minute drive of Cape Cod Beaches 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
A stay at this vacation home places you in the heart of Falmouth, within a 15-minute walk of Cape Cod Beaches and Main Street.
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
When you stay at this vacation home in Dennis Port, you'll be on the beach, just steps from Cape Cod Beaches and 6 minutes by foot from Sea Street Beach.
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
With a stay at this vacation home in South Yarmouth (Bass River), you'll be within a 10-minute drive of Cape Cod Beaches and Bass River Sports World.
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
A stay at this vacation home places you in the heart of Falmouth, within a 15-minute walk of Cape Cod Beaches and Spohr Gardens.
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
2896 Holiday Homes
Lowest Price
AU$128
Highest Price
AU$475
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 AU$189 per night from 1 Jan to 2 Jan
AU$189
1 Jan - 2 Jan 2026
includes taxes & fees
With a stay at Fairfield Inn & Suites by Marriott Cape Cod Hyannis, you'll be centrally located in Hyannis, within a 10-minute drive of Cape Cod Beaches and ...
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 AU$332 per night from 24 Dec to 25 Dec
AU$332
24 Dec - 25 Dec
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
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$187 per night from 30 Dec to 31 Dec
AU$187
30 Dec - 31 Dec
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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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 AU$128 per night from 28 Dec to 29 Dec
AU$128
28 Dec - 29 Dec
includes taxes & fees
Located in West Yarmouth, Cape Sands Inn is near the bay, within a 5-minute drive of John F. Kennedy Hyannis Museum and Hyannis Harbor.
Opens in a new windowCape Sands Inn
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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.