Orleans Vacation Rentals

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Check prices for these dates

In two weeks
Jan 9 - Jan 11
In two months
Feb 20 - Feb 22
In three months
Mar 20 - Mar 22
In four months
Apr 17 - Apr 19

Our top choices for Orleans vacation rentals

Terrace/patio
Beautiful home in Orleans. Park, Beach, Lake & Ocean. Telsa charge

Beautiful home in Orleans. Park, Beach, Lake & Ocean. Telsa charge

Beautiful home in Orleans. Park, Beach, Lake & Ocean. Telsa charge
Orleans
10.0 out of 10, Exceptional, (14)
"Property was clean and as described in the listing, owner was communicative and easy to check in"
United States
Darren Y.
The price is ￥281,826
￥491,173 total
includes taxes & fees
Dec 30 - Dec 31
Beautiful home in Orleans. Park, Beach, Lake & Ocean. Telsa charge
Dining
Historic charmer on the water with a firepit, kayaks, bikes, & firepit

Historic charmer on the water with a firepit, kayaks, bikes, & firepit

Historic charmer on the water with a firepit, kayaks, bikes, & firepit
Eastham
9.4 out of 10, Exceptional, (13)
"Absolutely perfect - would definitely come stay here again."
United States
William B.
The price is ￥53,704
￥137,135 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Historic charmer on the water with a firepit, kayaks, bikes, & firepit
Fridge, microwave, oven, stovetop
Darling, secluded cottage with large yard - walk to Chatham & Lighthouse Beach

Darling, secluded cottage with large yard - walk to Chatham & Lighthouse Beach

Darling, secluded cottage with large yard - walk to Chatham & Lighthouse Beach
Chatham
9.6 out of 10, Exceptional, (30)
"CutePrivateGreat outdoor showe "
United States
Stephanie D.
The price is ￥13,622
￥51,122 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Darling, secluded cottage with large yard - walk to Chatham & Lighthouse Beach
Beach
Cottage Oasis by Lake with Kayaks, Fire Pit & a Huge Yard

Cottage Oasis by Lake with Kayaks, Fire Pit & a Huge Yard

Cottage Oasis by Lake with Kayaks, Fire Pit & a Huge Yard
2.0 star property
Dennis
9.0 out of 10, Wonderful, (2)
"Very cute cottage. Very clean and grounds well manicured. "
United States
Anonymous traveler
The price is ￥20,198
￥50,803 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Cottage Oasis by Lake with Kayaks, Fire Pit & a Huge Yard
Fridge, microwave, oven, stovetop
Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!

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

Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!
2.0 star property
West Brewster
10.0 out of 10, Exceptional, (25)
"Lovely house with nice location."
United States
amy d.
The price is ￥23,486
￥112,714 total
includes taxes & fees
Jan 16 - Jan 17, 2026
Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!
Microwave, oven, stovetop, dishwasher
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK

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
9.6 out of 10, Exceptional, (102)
"Our second year in a row staying here. Cute house and great location! "
United States
Erin M.
The price is ￥15,344
￥65,462 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK
Outdoor dining
Spectacular Private Waterfront Cottage on Bayside. Panoramic Views. Pet Friendly

Spectacular Private Waterfront Cottage on Bayside. Panoramic Views. Pet Friendly

Spectacular Private Waterfront Cottage on Bayside. Panoramic Views. Pet Friendly
Wellfleet
10.0 out of 10, Exceptional, (75)
"Beautiful views in a quiet and private location. Cottage had everything we needed and nicely appointed."
United States
Janice H.
The price is ￥21,842
￥67,827 total
includes taxes & fees
Jan 2 - Jan 3, 2026
Spectacular Private Waterfront Cottage on Bayside. Panoramic Views. Pet Friendly
Outdoor dining
🦀Waterfront at The Velvet Crab~Amazing Sunsets

🦀Waterfront at The Velvet Crab~Amazing Sunsets

🦀Waterfront at The Velvet Crab~Amazing Sunsets
Eastham
9.8 out of 10, Exceptional, (23)
"Everything was great, we really enjoyed our stay!"
United States
Anna T.
The price is ￥24,345
￥66,927 total
includes taxes & fees
Jan 4 - Jan 5, 2026
🦀Waterfront at The Velvet Crab~Amazing Sunsets
Exterior
Cozy Large Home in Harwich with Patio near Wequassett Resort

Cozy Large Home in Harwich with Patio near Wequassett Resort

Cozy Large Home in Harwich with Patio near Wequassett Resort
Harwich
9.8 out of 10, Exceptional, (11)
"Host was very responsive and the house provided everything we needed. Great location! "
United States
Ashley M.
The price is ￥24,895
￥81,143 total
includes taxes & fees
Jan 9 - Jan 10, 2026
Cozy Large Home in Harwich with Patio near Wequassett Resort
Exterior detail
The Nantucket Room Unit - #2

The Nantucket Room Unit - #2

The Nantucket Room Unit - #2
Harwich port
9.8 out of 10, Exceptional, (49)
"amazing location and cute place to stay!"
United States
Adriana A.
The price is ￥46,971
￥70,792 total
includes taxes & fees
Dec 31 - Jan 1, 2026
The Nantucket Room Unit - #2
Outdoor dining
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

2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill
Dennis
9.8 out of 10, Exceptional, (178)
"Great location, clean property!"
United States
Lisa B.
The price is ￥13,950
￥48,940 total
includes taxes & fees
Dec 30 - Dec 31
2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill
Outdoor dining
Sleeps 2-8/Soaking Tub/FirePit~Burrows

Sleeps 2-8/Soaking Tub/FirePit~Burrows

Sleeps 2-8/Soaking Tub/FirePit~Burrows
Eastham
10.0 out of 10, Exceptional, (7)
"Overall, we had a really great stay. The home is in a quiet neighborhood & close to the beach. Everything was clean and as described in the listing. "
United States
Kallee M.
The price is ￥24,345
￥79,113 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Sleeps 2-8/Soaking Tub/FirePit~Burrows
Marina
Lovely House 5 Min to Beach with Deck, Grill, Garage

Lovely House 5 Min to Beach with Deck, Grill, Garage

Lovely House 5 Min to Beach with Deck, Grill, Garage
Eastham
10.0 out of 10, Exceptional, (1)
"Great house with comfy beds. Would consider staying again. "
United States
Susan C.
The price is ￥21,763
￥74,383 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Lovely House 5 Min to Beach with Deck, Grill, Garage
Smart TV, fireplace
The Pet-Friendly Surf Shack Hideaway on the Cove

The Pet-Friendly Surf Shack Hideaway on the Cove

The Pet-Friendly Surf Shack Hideaway on the Cove
Eastham
10.0 out of 10, Exceptional, (21)
"We loved the luxury bed linens, large kitchen & living area & the fact that it was pet friendly in a lovely neighborhood!"
United States
Jennifer G.
The price is ￥25,203
￥78,302 total
includes taxes & fees
Jan 4 - Jan 5, 2026
The Pet-Friendly Surf Shack Hideaway on the Cove
Beach nearby
Charming House by the Beach with Patio, Grill, FirePit

Charming House by the Beach with Patio, Grill, FirePit

Charming House by the Beach with Patio, Grill, FirePit
Bass River
9.8 out of 10, Exceptional, (7)
"Great location, walk to beach. Close to restaurants and pirate's cove mini golf. Beds were comfy. In-house laundry was convenient. Great outdoor shower. "
United States
Amanda W.
The price is ￥23,329
￥84,805 total
includes taxes & fees
Dec 30 - Dec 31
Charming House by the Beach with Patio, Grill, FirePit
Fridge, microwave, stovetop, dishwasher
Quaint condo near private beach access with fireplace - close to dining

Quaint condo near private beach access with fireplace - close to dining

Quaint condo near private beach access with fireplace - close to dining
Dennis Port
9.0 out of 10, Wonderful, (62)
"Clean, beautiful, great location "
United States
Jennifer B.
The price is ￥10,490
￥49,993 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Quaint condo near private beach access with fireplace - close to dining
Pool
Stylish 2nd floor Ocean Edge condo

Stylish 2nd floor Ocean Edge condo

Stylish 2nd floor Ocean Edge condo
Brewster
9.8 out of 10, Exceptional, (9)
"Great property. It looks like it was recently renovated and done really well. Convenient to the beaches and restaurants, and golf. We love Brewster. "
United States
Garret J.
The price is ￥27,869
￥67,019 total
includes taxes & fees
Dec 30 - Dec 31
Stylish 2nd floor Ocean Edge condo
Fridge, microwave, oven, stovetop
Sand Bar-Dog Friendly on Cooks Brook Beach

Sand Bar-Dog Friendly on Cooks Brook Beach

Sand Bar-Dog Friendly on Cooks Brook Beach
Eastham
10.0 out of 10, Exceptional, (23)
"Lovely time!"
United States
Joan W.
The price is ￥27,088
￥74,726 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Sand Bar-Dog Friendly on Cooks Brook Beach
Interior
National Seashore/Updated/Game Room~Blue Pearl

National Seashore/Updated/Game Room~Blue Pearl

National Seashore/Updated/Game Room~Blue Pearl
Eastham
10.0 out of 10, Exceptional, (8)
"Best rental we have stayed in on Cape, and we go every year. Exceptionally clean, comfortable. I can not say enough about it. Great location as well. What stood out the most was the high quality linens, as well as comfortable mattresses. It is very well kept with attention to detail. The grill and appliances were also of a higher quality and made it a pleasure to cook. Will absolutely stay at Blue Pearl again. "
United States
Nicole V.
The price is ￥24,345
￥77,142 total
includes taxes & fees
Dec 30 - Dec 31
National Seashore/Updated/Game Room~Blue Pearl
Fridge, microwave, oven, stovetop
Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail

Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail

Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail
West Brewster
9.6 out of 10, Exceptional, (50)
"House was perfect for our family reunion! "
United States
Gregg H.
The price is ￥22,390
￥83,916 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail
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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Top Orleans Hotel Reviews

Chatham Wayside Inn

Chatham Wayside Inn

10/10 Excellent
"Yes, lovely place to stay."
Angela 1-night trip
Posted 3 days ago
Chatham Wayside Inn

Find out more about Orleans

Search for holiday rentals in Orleans on Expedia! You can easily find your home rentals, villas, holiday apartments in Orleans using one of the methods below:

  • View our selection of featured holiday rentals in Orleans
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  • Enter your travel dates to view the best deals on holiday rentals in Orleans while they last

Look no further and take a look at our great range of rental properties in Orleans!

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Frequently asked questions

Can I find a vacation rental in Orleans?

Yes, we offer vacation rentals in Orleans near Orleans Bowling Center, or you can choose a more secluded option if you're looking for extra privacy while you relax. Visitors to Orleans speak positively about the beaches and seafood restaurants in this destination. Make sure you have time to check out the baseball games and university setting during your trip.

What's the top vacation rental in Orleans?

Luxury 7 BR, 4 BA w/ Unique 60 ft Pool, .4 Miles to Beach: This highly rated vacation home rental in Orleans is located near the beach and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 7 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a hot tub, and a selection of books so you can immerse yourself in your vacation.

How many vacation rentals are there in Orleans?

Choose from 290 Expedia vacation rentals in Orleans for a memorable vacation.

What’s there to see and do in Orleans?

Orleans Bowling Center and Cape Escape Adventure Golf are a couple of family-friendly sights, whereas cultural attractions include French Cable Station Museum and Academy Playhouse. Rock Harbor Beach and Skaket Beach are other places to visit while you're in town.

What are vacation rentals like in Orleans?

Vacation rentals are privately owned accommodations you can book for a couple days or more in Orleans. Vacation rentals feature amenities like WiFi and washers and dryers so you'll have everything you need. If you're concerned about cleanliness, a vacation rental can provide a sense of seclusion away from public hotel elevators and busy front desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is an attractive option for a family getaway.