Book Holiday Homes in Orleans

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Featured Holiday Homes in Orleans

Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK

Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK

Chatham
The price is NZ$766 per night from 16 Apr to 17 Apr
NZ$766
includes taxes & fees
16 Apr - 17 Apr
Stay at this vacation home in Chatham. Enjoy a water park, a garden, and patios. Popular attractions Hardings Beach and Ridgevale Beach are located nearby.
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK
WATERFRONT w/Kayaks & SUP’s ★ Pet friendly ★ HOT TUB★Firepit & FPL★Deck & Patio

WATERFRONT w/Kayaks & SUP’s ★ Pet friendly ★ HOT TUB★Firepit & FPL★Deck & Patio

Yarmouth
Book a stay at this beach vacation home in South Yarmouth. Enjoy free WiFi, a beach locale, and a water park. Popular attractions Hyannis Harbor and Cape Cod ...
WATERFRONT w/Kayaks & SUP’s ★ Pet friendly ★ HOT TUB★Firepit & FPL★Deck & Patio
Sand Bar-Dog Friendly on Cooks Brook Beach

Sand Bar-Dog Friendly on Cooks Brook Beach

Eastham
The price is NZ$969 per night from 6 Apr to 7 Apr
NZ$969
includes taxes & fees
6 Apr - 7 Apr
Book a stay at this beach vacation home in Eastham. Enjoy free WiFi, a beach locale, and patios. Popular attractions Cape Cod National Seashore and Cooks Brook ...
Sand Bar-Dog Friendly on Cooks Brook Beach
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Dog-friendly home with large yard - walk to Great Pond & Kingsbury Beach

Dog-friendly home with large yard - walk to Great Pond & Kingsbury Beach

Eastham
Stay at this vacation home in Eastham. Enjoy a garden, patios, and an in-room coffeemaker. Popular attractions Herring Brook Beach and Thumpertown Beach are ...
Dog-friendly home with large yard - walk to Great Pond & Kingsbury Beach
OCEANFRONT, PRIVATE BEACH AND DECK, AMAZING VIEWS, KAYAKS, 2 Story House, 4+BR

OCEANFRONT, PRIVATE BEACH AND DECK, AMAZING VIEWS, KAYAKS, 2 Story House, 4+BR

west yarmouth, Cape Cod
Book a stay at this beach vacation home in South Yarmouth. Enjoy free WiFi, a beach locale, and a water park. Popular attractions Hyannis Harbor and Cape Cod ...
OCEANFRONT, PRIVATE BEACH AND DECK, AMAZING VIEWS, KAYAKS, 2 Story House, 4+BR
Secluded home with firepit, & scenic yard - near Nauset Beach & shops

Secluded home with firepit, & scenic yard - near Nauset Beach & shops

Eastham
Stay at this vacation home in Eastham. Enjoy a garden, laundry facilities, and patios. Popular attractions Cape Cod National Seashore and Poit's Lighthouse Mini ...
Secluded home with firepit, & scenic yard - near Nauset Beach & shops
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
Stay at this vacation home in Dennis Port. Enjoy free WiFi, a water park, and balconies or patios. Popular attractions Cape Cod Theatre Company – Home of the ...
2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill
Waterfront, Incredible Views and Private Dock!

Waterfront, Incredible Views and Private Dock!

Yarmouth
Stay at this vacation home in South Yarmouth. Enjoy a garden, patios, and cable/satellite TV service. Popular attractions Cape Cod Rail Trail and Bass River ...
Waterfront, Incredible Views and Private Dock!
Unique Oyster Pond 3bd-2ba home in private setting close to downtown.

Unique Oyster Pond 3bd-2ba home in private setting close to downtown.

Chatham
Book a stay at this family-friendly vacation home in Chatham. Enjoy free WiFi, a garden, and furnished patios. Popular attractions Chatham Railroad Museum and ...
Unique Oyster Pond 3bd-2ba home in private setting close to downtown.
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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.

Orleans 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 Orleans vacation homes are the perfect way for you to wing it.

Holiday houses in Orleans 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 Orleans 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 Orleans adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Orleans 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 Orleans 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.

Orleans Holiday Homes essential information

Accommodation
2498 Holiday Homes
Lowest Price
NZ$221
Highest Price
NZ$969
Popular accommodation
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK, WATERFRONT w/Kayaks & SUP’s ★ Pet friendly ★ HOT TUB★Firepit & FPL★Deck & Patio , Sand Bar-Dog Friendly on Cooks Brook Beach, Dog-friendly home with large yard - walk to Great Pond & Kingsbury Beach, OCEANFRONT, PRIVATE BEACH AND DECK, AMAZING VIEWS, KAYAKS, 2 Story House, 4+BR, Secluded home with firepit, & scenic yard - near Nauset Beach & shops, 2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill, Waterfront, Incredible Views and Private Dock!, Unique Oyster Pond 3bd-2ba home in private setting close to downtown.

Top trending hotels in Orleans

Skaket Beach Motel

Skaket Beach Motel

2 out of 5
203 Cranberry Hwy, Orleans, MA
The price is NZ$221 per night from 16 Apr to 17 Apr
NZ$221
includes taxes & fees
16 Apr - 17 Apr
Book a stay at this business-friendly motel in Orleans. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Skaket Beach Motel
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$419 per night from 6 Apr to 7 Apr
NZ$419
includes taxes & fees
6 Apr - 7 Apr
Stay at this 4-star family-friendly resort in Hyannis. Enjoy free WiFi, free parking, and 2 restaurants. Our guests praise the clean rooms in our reviews. Popular ...
Margaritaville Resort Cape Cod
Bayside Resort Hotel

Bayside Resort Hotel

3 out of 5
225 Route 28, West Yarmouth, MA
Fully refundableReserve now, pay when you stay
The price is NZ$261 per night from 6 Apr to 7 Apr
NZ$261
includes taxes & fees
6 Apr - 7 Apr
Stay at this 3-star beach hotel in West Yarmouth. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our reviews. ...
Bayside Resort Hotel
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Hampton Inn & Suites Cape Cod-West Yarmouth

Hampton Inn & Suites Cape Cod-West Yarmouth

2.5 out of 5
99 Main Street, Route 28, West Yarmouth, MA
Fully refundableReserve now, pay when you stay
The price is NZ$254 per night from 9 Apr to 10 Apr
NZ$254
includes taxes & fees
9 Apr - 10 Apr
Book a stay at this family-friendly hotel in West Yarmouth. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Hampton Inn & Suites Cape Cod-West Yarmouth
Don't see what you're looking for?
See all available properties in Orleans
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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.