Wooden beach chairs and a wooden staircase on a sandy beach with a hilly background.

Orleans Holiday Rentals

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Our top choices for Orleans holiday rentals

1. Captain's Quarters by Nauset Beach

Captain's Quarters by Nauset Beach
East Orleans
10.0 out of 10, Exceptional, (12 reviews)
"Cape Cod cottage close to the beach."
United States
Bill B.
The price is NZ$964
includes taxes & fees
13 Oct - 14 Oct
Captain's Quarters by Nauset Beach

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

Beautiful home in Orleans. Park, Beach, Lake & Ocean. Telsa charge
Orleans
9.8 out of 10, Exceptional, (18 reviews)
"Property was clean and as described in the listing, owner was communicative and easy to check in"
United States
Darren Y.
The price is NZ$5,366
includes taxes & fees
19 Oct - 20 Oct
Beautiful home in Orleans. Park, Beach, Lake & Ocean. Telsa charge

3. Brewster Green Resort

Brewster Green Resort
3.5 star property
Brewster
9.4 out of 10, Exceptional, (146 reviews)
"Very spacious rooms clean ,great location friendly staff,"
United States
Margaret
The price is NZ$425
includes taxes & fees
1 Oct - 2 Oct
Brewster Green Resort

4. On Town Cove with salt water access! Kayaks and paddle board available for use!

On Town Cove with salt water access! Kayaks and paddle board available for use!
Eastham
9.8 out of 10, Exceptional, (66 reviews)
"Clean, great location. "
United States
Peter G.
The price is NZ$790
includes taxes & fees
19 Oct - 20 Oct
On Town Cove with salt water access! Kayaks and paddle board available for use!

5. 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, (28 reviews)
"Our host was very responsive and all the instructions were clear. The house was immaculate and a perfect spot of a winter getaway. Would stay again!"
United States
Anna P.
The price is NZ$877
includes taxes & fees
5 Oct - 6 Oct
The Pet-Friendly Surf Shack Hideaway on the Cove

6. 10 min walk to Beach - Home with Amazing View & Huge Deck

10 min walk to Beach - Home with Amazing View & Huge Deck
Eastham
The price is NZ$1,005
includes taxes & fees
12 Oct - 13 Oct
10 min walk to Beach - Home with Amazing View & Huge Deck

7. 🌊The Ocean Cottage on Thumpertown Beach

🌊The Ocean Cottage on Thumpertown Beach
Eastham
9.4 out of 10, Exceptional, (13 reviews)
"We absolutely loved the place and the location right near Thumpertown Beach was perfect!"
United States
Jeff P.
The price is NZ$699
includes taxes & fees
13 Oct - 14 Oct
🌊The Ocean Cottage on Thumpertown Beach

8. 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, (4 reviews)
"Great house with comfy beds. Would consider staying again. "
United States
Susan C.
The price is NZ$862
includes taxes & fees
26 Oct - 27 Oct
Lovely House 5 Min to Beach with Deck, Grill, Garage

9. Solace in the Sun- Adj. Beds/Game Rm/Soakng Tub/Dog Ok

Solace in the Sun- Adj. Beds/Game Rm/Soakng Tub/Dog Ok
Eastham
10.0 out of 10, Exceptional, (4 reviews)
"Our family enjoyed the downstairs activities, especially nice for the kids to play and adults upstairs. All the bedrooms/baths clean and very nice. Loved our stay. "
United States
Donna R.
The price is NZ$1,147
includes taxes & fees
1 Oct - 2 Oct
Solace in the Sun- Adj. Beds/Game Rm/Soakng Tub/Dog Ok

10. The Alpine/Walk to Beach for 2 or more!

The Alpine/Walk to Beach for 2 or more!
Eastham
9.2 out of 10, Wonderful, (12 reviews)
"The location was awesome, the house was clean and spacious, and overall it was terrific! I would highly recommend."
United States
Jennifer G.
The price is NZ$913
includes taxes & fees
5 Oct - 6 Oct
The Alpine/Walk to Beach for 2 or more!

11. National Seashore/Updated/Game Room~Blue Pearl

National Seashore/Updated/Game Room~Blue Pearl
Eastham
10.0 out of 10, Exceptional, (9 reviews)
"We had an wonderful experience staying at this house. It was exceptionally clean and it had everything we needed (it was nice to have linens and towels provided). All of the rooms were relaxing and comfortable and the kitchen was very well equipped. I would definitely stay there again. "
United States
Catharine D.
The price is NZ$875
includes taxes & fees
5 Oct - 6 Oct
National Seashore/Updated/Game Room~Blue Pearl

12. The Breeze on Minister's Pond

The Breeze on Minister's Pond
Eastham
10.0 out of 10, Exceptional, (26 reviews)
"The Breeze is the cutest, warmest, comfiest home. We thoroughly enjoyed our stay and will definitely book again!"
United States
MelanieC
The price is NZ$740
includes taxes & fees
19 Oct - 20 Oct
The Breeze on Minister's Pond

13. Hot Tub/Kayaks/Ebikes/Waterfront-The Lotus

Hot Tub/Kayaks/Ebikes/Waterfront-The Lotus
Eastham
10.0 out of 10, Exceptional, (21 reviews)
"Just a great location, and a very comfortable place. We loved the porch bed and chair. We are looking forward to returning."
United States
David B.
The price is NZ$877
includes taxes & fees
20 Oct - 21 Oct
Hot Tub/Kayaks/Ebikes/Waterfront-The Lotus

14. Edgewood on Campground Beach/Steps to the Sand

Edgewood on Campground Beach/Steps to the Sand
Eastham
10.0 out of 10, Exceptional, (10 reviews)
"Cozy cottage right by the beach. Great area not for to restaurants and beaches. Would definitely stay again!"
United States
Melinda W.
The price is NZ$857
includes taxes & fees
13 Oct - 14 Oct
Edgewood on Campground Beach/Steps to the Sand

15. Pondside/Kayak/Firepit/Dog Friendly~Willow Haven

Pondside/Kayak/Firepit/Dog Friendly~Willow Haven
Eastham
9.8 out of 10, Exceptional, (7 reviews)
"Great hideaway location on the Cape. Well equipped rental."
United Kingdom
Richard F.
The price is NZ$664
includes taxes & fees
19 Oct - 20 Oct
Pondside/Kayak/Firepit/Dog Friendly~Willow Haven

16. 🦀Waterfront at The Velvet Crab~Amazing Sunsets

🦀Waterfront at The Velvet Crab~Amazing Sunsets
Eastham
9.8 out of 10, Exceptional, (28 reviews)
"Perfect size home for a family of 4, welcoming and cozy! Having -All towels and linens and shampoo, body wash and conditioner all included made for a much easier stay! Highly recommend."
United States
Emily A.
The price is NZ$774
includes taxes & fees
19 Oct - 20 Oct
🦀Waterfront at The Velvet Crab~Amazing Sunsets

17. Pond House~Waterfront Oasis on Minister's Pond

Pond House~Waterfront Oasis on Minister's Pond
Eastham
10.0 out of 10, Exceptional, (13 reviews)
"Had everything we needed for a comfortable stay."
United States
BILL
The price is NZ$911
includes taxes & fees
5 Oct - 6 Oct
Pond House~Waterfront Oasis on Minister's Pond

18. 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, (14 reviews)
"Great host. Convenient location for a visit to Chatham."
United States
Bill F.
The price is NZ$884
includes taxes & fees
7 Oct - 8 Oct
Cozy Large Home in Harwich with Patio near Wequassett Resort

19. Driftwood Cottages - 65A - Whale

Driftwood Cottages - 65A - Whale
Eastham
The price is NZ$1,443
includes taxes & fees
1 Oct - 2 Oct
Driftwood Cottages - 65A - Whale

20. Sleeps 2-8/Soaking Tub/FirePit~Burrows

Sleeps 2-8/Soaking Tub/FirePit~Burrows
Eastham
10.0 out of 10, Exceptional, (8 reviews)
"We went with a small group of friends and everything was amazing. The property is beautiful and well located. We had everything that we needed and the communication con the owner was good."
United States
Lourdes P.
The price is NZ$904
includes taxes & fees
5 Oct - 6 Oct
Sleeps 2-8/Soaking Tub/FirePit~Burrows
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

Find out more about Orleans

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Orleans holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Orleans. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Orleans. Seeing all the best attractions is bound to make you fall in love with Orleans. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Orleans short-term rentals, that won’t be hard to do.

Frequently asked questions

Can I find a holiday rental in Orleans?

Yes, there are holiday rentals in Orleans close to Cape Escape Adventure Golf, or you can select a more secluded option if you're looking for a relaxing stay. 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 are some of the best holiday rentals that Orleans has to offer?

Beautiful home in Orleans. Park, Beach, Lake & Ocean. Telsa charge: This highly rated holiday home rental in Orleans is located on a lake, and has a balcony, a garden and a BBQ 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 that you can cook with friends or family. Another good choice for your trip to Orleans is 5 bedrooms ocean view estate overlooking cape cod bay.

How many holiday rentals are there in Orleans?

Choose from 284 Expedia holiday rentals in Orleans for a memorable holiday.

What’s there to see and do in Orleans?

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

What are holiday rentals like in Orleans?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Orleans. Holiday rentals feature amenities like kitchens and laundry facilities so you'll feel just like you're at home. If you're concerned about a sanitised environment, a holiday rental can provide a sense of seclusion away from public hotel lifts and lobbies packed with people while still allowing you the enjoyment of travel. You'll also get more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular option for family gatherings.