Book Holiday Homes in Orleans

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Featured Holiday Homes in Orleans

Pet Friendly,Quiet family neighborhood with  private fenced in yard with hot tub

Pet Friendly,Quiet family neighborhood with private fenced in yard with hot tub

south yarmouth
When you stay at this vacation home in South Yarmouth, you'll be by the sea, within a 5-minute drive of Bass River Sports World and Edward Gorey House.
Pet Friendly,Quiet family neighborhood with private fenced in yard with hot tub
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
The price is AU$1,164 per night from 5 Jan to 6 Jan
AU$1,164
includes taxes & fees
5 Jan - 6 Jan 2025
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 Cape Cod Museum of Natural ...
Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!
Charming Home Close to Everything.  Discounts for the fall and winter

Charming Home Close to Everything. Discounts for the fall and winter

Eastham
When you stay at this vacation home in Eastham, you'll be by the sea, within a 5-minute drive of Poit's Lighthouse Mini Golf and Arnold's Mini Golf.
Charming Home Close to Everything. Discounts for the fall and winter
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Beautiful waterfront home- mins to beach, fishing /kayak right from the backyard

Beautiful waterfront home- mins to beach, fishing /kayak right from the backyard

Yarmouth
When you stay at this vacation home in South Yarmouth, you'll be on the waterfront, within a 5-minute drive of Bass River Sports World and Edward Gorey ...
Beautiful waterfront home- mins to beach, fishing /kayak right from the backyard
Cozy Spacious Home Walk to the Beach & 1 Mile to Downtown Hyannis

Cozy Spacious Home Walk to the Beach & 1 Mile to Downtown Hyannis

Barnstable
The price is AU$779 per night from 1 Jan to 2 Jan
AU$779
includes taxes & fees
1 Jan - 2 Jan 2025
When you stay at this vacation home in Hyannis, you'll be near the beach, within a 10-minute walk of Cape Cod Beaches and Keyes Beach.
Cozy Spacious Home Walk to the Beach & 1 Mile to Downtown Hyannis
Affordable Cape Cod Get Away!

Affordable Cape Cod Get Away!

Eastham
With a stay at this vacation home in Eastham, you'll be within a 10-minute walk of Cape Cod Beaches and Cooks Brook Beach.
Affordable Cape Cod Get Away!
Comfy Cape Home: Close to Mayflower Beach, golf course, and Downtown

Comfy Cape Home: Close to Mayflower Beach, golf course, and Downtown

Dennis
With a stay at this vacation home in Dennis, you'll be within a 5-minute drive of Cape Playhouse and Scargo Hill Observation Tower.
Comfy Cape Home: Close to Mayflower Beach, golf course, and Downtown
Beautiful Views of Cape Cod Bay!

Beautiful Views of Cape Cod Bay!

North Truro
With a stay at this vacation home in North Truro, you'll be steps from Cape Cod Beaches and a 2-minute drive from Cape Cod National Seashore.
Beautiful Views of Cape Cod Bay!
Relaxing Retreat with Firepit & Outdoor Shower - Near Atlantic & Cape Cod Bay

Relaxing Retreat with Firepit & Outdoor Shower - Near Atlantic & Cape Cod Bay

Dennis
Located in Dennis, this vacation home is by the sea, within a 5-minute drive of Cape Playhouse and Scargo Hill Observation Tower.
Relaxing Retreat with Firepit & Outdoor Shower - Near Atlantic & Cape Cod Bay
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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
2025 Holiday Homes
Lowest Price
AU$214
Highest Price
AU$1,164
Popular accommodation
Pet Friendly,Quiet family neighborhood with private fenced in yard with hot tub, Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!, Charming Home Close to Everything. Discounts for the fall and winter , Beautiful waterfront home- mins to beach, fishing /kayak right from the backyard, Cozy Spacious Home Walk to the Beach & 1 Mile to Downtown Hyannis, Affordable Cape Cod Get Away!, Comfy Cape Home: Close to Mayflower Beach, golf course, and Downtown , Beautiful Views of Cape Cod Bay!, Relaxing Retreat with Firepit & Outdoor Shower - Near Atlantic & Cape Cod Bay

Top trending hotels in Orleans

Nauset Beach Inn

Nauset Beach Inn

3 out of 5
237 Beach Road, Orleans, MA
The price is AU$388 per night from 2 Jan to 3 Jan
AU$388
includes taxes & fees
2 Jan - 3 Jan 2025
With a stay at Nauset Beach Inn in Orleans (East Orleans), you'll be within a 5-minute walk of Cape Cod Beaches and Nauset Beach.
Nauset Beach Inn
Lakefront retreat w/ deck, dock, sandy beach, 4 watercraft, <6 mins to 2 beaches

Lakefront retreat w/ deck, dock, sandy beach, 4 watercraft, <6 mins to 2 beaches

Orleans
A stay at this condo places you in the heart of Orleans, a 2-minute drive from Orleans Bowling Center and 5 minutes from Captain's Cove Golf Course.
Lakefront retreat w/ deck, dock, sandy beach, 4 watercraft, <6 mins to 2 beaches
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 AU$214 per night from 1 Jan to 2 Jan
AU$214
includes taxes & fees
1 Jan - 2 Jan 2025
With a stay at Bayside Resort Hotel in West Yarmouth, you'll be near the bay, just a 1-minute walk from Main Street and 8 minutes by foot from Putter's Paradise ...
Bayside Resort Hotel
Save an average of 15% on thousands of hotels when you're signed in
Margaritaville Resort Cape Cod

Margaritaville Resort Cape Cod

3 out of 5
1225 Iyannough Rd, Hyannis, MA
Fully refundable
The price is AU$309 per night from 1 Jan to 2 Jan
AU$309
includes taxes & fees
1 Jan - 2 Jan 2025
With a stay at Margaritaville Resort Cape Cod in Hyannis, you'll be in a shopping district, just steps from Cape Codder Water Park and a 4-minute drive from ...
Margaritaville Resort Cape Cod
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.