Book Holiday Homes in Orleans

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Featured Holiday Homes in Orleans

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
The price is AU$483 per night from 14 Nov to 15 Nov
AU$483
14 Nov - 15 Nov
includes taxes & fees
With a stay at this vacation home in Dennis Port, you'll be by the sea, within a 15-minute drive of Mayflower Beach 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
Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!

Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!

2 out of 5
Brewster
With a stay at this vacation home in Brewster (West Brewster), you'll be a 2-minute drive from Sheep Pond and 6 minutes from Breakwater Beach.
Opens in a new windowCoastal Cape Cod 3 bedroom close to the beach, bike path & ponds!
Mid-Cape Remodeled House with WiFi, AC, Smart TV, Laundry, and Fenced-in Yard

Mid-Cape Remodeled House with WiFi, AC, Smart TV, Laundry, and Fenced-in Yard

2 out of 5
Yarmouth
Located in South Yarmouth, this vacation home is within a 5-minute drive of Bass River Sports World and Captain Bangs Hallett House.
Opens in a new windowMid-Cape Remodeled House with WiFi, AC, Smart TV, Laundry, and Fenced-in Yard
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Oceanfront Escape house on SeaView Beach, Dog-Friendly!

Oceanfront Escape house on SeaView Beach, Dog-Friendly!

South Yarmouth
With a stay at this vacation home in South Yarmouth (Bass River), you'll be steps from Cape Cod Beaches and Thachers Beach.
Opens in a new windowOceanfront Escape house on SeaView Beach, Dog-Friendly!
Spacious, private cottage just a few minutes walk to Ridgevale Beach!

Spacious, private cottage just a few minutes walk to Ridgevale Beach!

Chatham
When you stay at this vacation home in West Chatham, you'll be by the sea, within a 10-minute walk of Ridgevale Beach and Cape Cod Beaches.
Opens in a new windowSpacious, private cottage just a few minutes walk to Ridgevale Beach!
Steps to a private bay beach from this private & Charming Cape! Book this Fall!

Steps to a private bay beach from this private & Charming Cape! Book this Fall!

Eastham
With a stay at this vacation home in Eastham, you'll be by the sea, just a 2-minute walk from Cape Cod Beaches and 7 minutes by foot from Campground Beach.
Opens in a new windowSteps to a private bay beach from this private & Charming Cape! Book this Fall!
Downtown Chatham Luxury 9 BR Home with Heated Pool.  Pets welcome!

Downtown Chatham Luxury 9 BR Home with Heated Pool. Pets welcome!

Chatham
A stay at this vacation home places you in the heart of Chatham, within a 5-minute walk of Mayo House and Chatham Windmill.
Opens in a new windowDowntown Chatham Luxury 9 BR Home with Heated Pool. Pets welcome!
Breathtaking Riverfront Home with a Lovely Deck, Close to Beach - Dogs OK

Breathtaking Riverfront Home with a Lovely Deck, Close to Beach - Dogs OK

Chatham
Located in Chatham, this vacation home is by the sea, within a 5-minute drive of Hardings Beach and Cape Cod Beaches.
Opens in a new windowBreathtaking Riverfront Home with a Lovely Deck, Close to Beach - Dogs OK
Charming Hyannis 3 Bed 2 Bath

Charming Hyannis 3 Bed 2 Bath

Barnstable
When you a stay at this vacation home in Hyannis, you'll be on the waterfront, within a 5-minute walk of Main Street Hyannis and Cape Cod Hospital.
Opens in a new windowCharming Hyannis 3 Bed 2 Bath
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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
2604 Holiday Homes
Lowest Price
AU$131
Highest Price
AU$483
Popular accommodation
2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill, Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!, Mid-Cape Remodeled House with WiFi, AC, Smart TV, Laundry, and Fenced-in Yard, Oceanfront Escape house on SeaView Beach, Dog-Friendly!, Spacious, private cottage just a few minutes walk to Ridgevale Beach!, Steps to a private bay beach from this private & Charming Cape! Book this Fall!, Downtown Chatham Luxury 9 BR Home with Heated Pool. Pets welcome!, Breathtaking Riverfront Home with a Lovely Deck, Close to Beach - Dogs OK, Charming Hyannis 3 Bed 2 Bath

Top trending hotels in Orleans

Rodeway Inn Orleans - Cape Cod

Rodeway Inn Orleans - Cape Cod

2 out of 5
48 Cranberry Hwy, Orleans, MA
Fully refundableReserve now, pay when you stay
The price is AU$184 per night from 16 Nov to 17 Nov
AU$184
16 Nov - 17 Nov
includes taxes & fees
A stay at Rodeway Inn Orleans - Cape Cod places you in the heart of Orleans, within a 5-minute drive of Orleans Bowling Center and Cape Cod Beaches.
Opens in a new windowRodeway Inn Orleans - Cape Cod
Luxury 7 BR, 4 BA w/ Unique 60 ft Pool, .4 Miles to Beach

Luxury 7 BR, 4 BA w/ Unique 60 ft Pool, .4 Miles to Beach

Orleans
When you stay at this vacation home in Orleans, you'll be near the beach, within a 5-minute drive of Captains Golf Course and Cape Cod Beaches.
Opens in a new windowLuxury 7 BR, 4 BA w/ Unique 60 ft Pool, .4 Miles to Beach
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$184 per night from 30 Nov to 1 Dec
AU$184
30 Nov - 1 Dec
includes taxes & fees
A stay at Fairfield Inn & Suites by Marriott Cape Cod Hyannis places you in the heart of Hyannis, within a 5-minute drive of Cape Codder Water Park and John ...
Opens in a new windowFairfield Inn & Suites by Marriott Cape Cod Hyannis
Save an average of 15% on thousands of hotels when you're signed in
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$131 per night from 15 Nov to 16 Nov
AU$131
15 Nov - 16 Nov
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
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.