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. 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, (17 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$5,508
includes taxes & fees
28 Aug - 29 Aug
Beautiful home in Orleans. Park, Beach, Lake & Ocean. Telsa charge

2. Brewster Green Resort

Brewster Green Resort
3.5 star property
Brewster
9.4 out of 10, Exceptional, (140 reviews)
"Nice resort. Well maintained, very quiet, off the beaten path. Everything in good working order, Staff very nice. Will stay here again. Great location!"
United States
Kevin
The price is NZ$448
includes taxes & fees
15 Sept - 16 Sept
Brewster Green Resort

3. 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, (63 reviews)
"Clean, great location. "
United States
Peter G.
The price is NZ$711
includes taxes & fees
12 Sept - 13 Sept
On Town Cove with salt water access! Kayaks and paddle board available for use!

4. 6 Mi to Beach: Home w/ Deck in Brewster!

6 Mi to Beach: Home w/ Deck in Brewster!
3.0 star property
Brewster
The price is NZ$1,171
includes taxes & fees
17 Aug - 18 Aug
6 Mi to Beach: Home w/ Deck in Brewster!

5. Quiet getaway in a unique area of Cape Cod

Quiet getaway in a unique area of Cape Cod
Brewster
10.0 out of 10, Exceptional, (5 reviews)
"Perfect for a quiet getaway. Owner was in Constant contact. If I had a question replied very quickly. I highly recommend staying here."
United States
Anonymous traveller
The price is NZ$792
includes taxes & fees
29 Aug - 30 Aug
Quiet getaway in a unique area of Cape Cod

6. 🐳 The Whale Song - Dog-Friendly Studio

🐳 The Whale Song - Dog-Friendly Studio
Eastham
9.6 out of 10, Exceptional, (15 reviews)
"We enjoyed our stay very much "
United States
Gregg P.
The price is NZ$568
includes taxes & fees
23 Aug - 24 Aug
🐳 The Whale Song - Dog-Friendly Studio

7. 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, (3 reviews)
"Great house with comfy beds. Would consider staying again. "
United States
Susan C.
The price is NZ$963
includes taxes & fees
9 Sept - 10 Sept
Lovely House 5 Min to Beach with Deck, Grill, Garage

8. 🐚The Bay Cottage on Thumpertown Beach

🐚The Bay Cottage on Thumpertown Beach
Eastham
9.8 out of 10, Exceptional, (13 reviews)
"My group and I had another wonderful stay at the Bay Cottage! The space is sparkling clean when we arrived and the location cannot be beat. Tara is also very responsive and attentive which makes for an even better stay!"
United States
Sophia I.
The price is NZ$765
includes taxes & fees
30 Aug - 31 Aug
🐚The Bay Cottage on Thumpertown Beach

9. 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$943
includes taxes & fees
9 Sept - 10 Sept
Hot Tub/Kayaks/Ebikes/Waterfront-The Lotus

10. 🦀Waterfront at The Velvet Crab~Amazing Sunsets

🦀Waterfront at The Velvet Crab~Amazing Sunsets
Eastham
9.8 out of 10, Exceptional, (26 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$901
includes taxes & fees
13 Sept - 14 Sept
🦀Waterfront at The Velvet Crab~Amazing Sunsets

11. Eastham, Cape Cod - Town Cove Waterfront. Newly renovated and insulated sunporch

Eastham, Cape Cod - Town Cove Waterfront. Newly renovated and insulated sunporch
Eastham
9.0 out of 10, Wonderful, (102 reviews)
"Awesome location, private and peaceful."
United States
Kathy D.
The price is NZ$965
includes taxes & fees
1 Sept - 2 Sept
Eastham, Cape Cod - Town Cove Waterfront. Newly renovated and insulated sunporch

12. 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, (13 reviews)
"Host was very responsive and the house provided everything we needed. Great location! "
United States
Ashley M.
The price is NZ$892
includes taxes & fees
7 Sept - 8 Sept
Cozy Large Home in Harwich with Patio near Wequassett Resort

13. 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.
Edgewood on Campground Beach/Steps to the Sand

14. The Brewster Pearl

The Brewster Pearl
Brewster
10.0 out of 10, Exceptional, (2 reviews)
"The home is so beautiful and the decor is like out of a magazine. Immaculately clean, our standards are high, being hosts ourselves. Every amenity thoughtfully provided. The furnishings, bedding, towels are of premium quality and top brand. Our host was incredible, responsive, kind and helpful. This home is perfectly located to many beaches , excellent restaurants and coffee shops. Brewster is a special place. I can understand why the owner chose it. Our family was immensely blessed to have the...
United States
PAULA
The price is NZ$1,395
includes taxes & fees
8 Sept - 9 Sept
The Brewster Pearl

15. 2021 CONSTRUCTION 3BR 3BA. Close to Bike Trail & Beaches. Central AC, Firepit.

2021 CONSTRUCTION 3BR 3BA. Close to Bike Trail & Beaches. Central AC, Firepit.
Eastham
10.0 out of 10, Exceptional, (47 reviews)
"Kitchen was well equipped. Very good location for us and comfy beds. I highly recommend this property and the host. "
United States
Mark T R.
The price is NZ$1,727
includes taxes & fees
6 Sept - 7 Sept
2021 CONSTRUCTION 3BR 3BA. Close to Bike Trail & Beaches. Central AC, Firepit.

16. 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$1,165
includes taxes & fees
4 Sept - 5 Sept
The Breeze on Minister's Pond

17. Gray Whale-Minutes to Eastham Bay & Ocean Beaches

Gray Whale-Minutes to Eastham Bay & Ocean Beaches
Eastham
10.0 out of 10, Exceptional, (6 reviews)
"very well appointed accommodations - great location - helpful amenities. would come back again!"
United States
Leonard
The price is NZ$1,238
includes taxes & fees
12 Sept - 13 Sept
Gray Whale-Minutes to Eastham Bay & Ocean Beaches

18. 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, (51 reviews)
"House was perfect for our family reunion! "
United States
Gregg H.
The price is NZ$1,347
includes taxes & fees
8 Sept - 9 Sept
Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail

19. Ocean Edge Cape Cod 2 Bed 2 Bath, Golf & Free Resort Access - Brewster, MA

Ocean Edge Cape Cod 2 Bed 2 Bath, Golf & Free Resort Access - Brewster, MA
Brewster
10.0 out of 10, Exceptional, (50 reviews)
"We did a quick overnight The amenities were great and the condo was perfect !!!"
United States
Katie M.
The price is NZ$1,029
includes taxes & fees
11 Sept - 12 Sept
Ocean Edge Cape Cod 2 Bed 2 Bath, Golf & Free Resort Access - Brewster, MA

20. 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, (104 reviews)
"Our second year in a row staying here. Cute house and great location! "
United States
Erin M.
The price is NZ$1,145
includes taxes & fees
30 Aug - 31 Aug
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK
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.

How many holiday rentals are there in Orleans?

Choose from 287 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. Cape Cod Beaches and Skaket 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.