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

Holiday Homes in Orleans

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Check prices for these dates

In two weeks
11 Sept - 13 Sept
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Orleans holiday homes

A modern kitchen with white cabinets, a central island, and a dining area with a table set for four.

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, (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 €2,896
includes taxes & fees
5 Sept - 6 Sept
Beautiful home in Orleans. Park, Beach, Lake & Ocean. Telsa charge
A covered deck with a grill, outdoor furniture, and a view of trees.

2. Great for Families! Brewster Home 6 Mi to Beach

Great for Families! Brewster Home 6 Mi to Beach
Brewster
10.0 out of 10, Exceptional, (11 reviews)
"The kitchen was well stocked. The Beds were comfortable. "
United States
Stacey P.
The price is €612
includes taxes & fees
1 Sept - 2 Sept
Great for Families! Brewster Home 6 Mi to Beach
A row of white buildings with storefronts, including a visible sign for 'Chatham' and a 'Chatham' sign above a window.

3. 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 €435
includes taxes & fees
28 Sept - 29 Sept
Lovely House 5 Min to Beach with Deck, Grill, Garage
A living room with a grey sofa, striped rug, and a lamp.

4. 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, (26 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 €499
includes taxes & fees
28 Sept - 29 Sept
The Pet-Friendly Surf Shack Hideaway on the Cove
A spacious living area with wooden floors, a large dining table, and multiple windows offering a view of the beach.

5. 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 €559
includes taxes & fees
28 Sept - 29 Sept
10 min walk to Beach - Home with Amazing View & Huge Deck
A dining table set with plates, glasses, and a charcuterie board with cheese, grapes, and crackers.

6. 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 €479
includes taxes & fees
29 Sept - 30 Sept
National Seashore/Updated/Game Room~Blue Pearl

7. 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 €617
includes taxes & fees
29 Sept - 30 Sept
Solace in the Sun- Adj. Beds/Game Rm/Soakng Tub/Dog Ok
A resort with a large pool, sun loungers, and a pier extending into the water.

8. 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)
"Host was very responsive and the house provided everything we needed. Great location! "
United States
Ashley M.
The price is €430
includes taxes & fees
28 Sept - 29 Sept
Cozy Large Home in Harwich with Patio near Wequassett Resort
A wooden outdoor shed with a door, a window, and a gravel path leading to it.

9. 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 €512
includes taxes & fees
30 Sept - 1 Oct
Gray Whale-Minutes to Eastham Bay & Ocean Beaches
A beach with a wooden fence and a clear view of the ocean.

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 €532
includes taxes & fees
29 Sept - 30 Sept
The Alpine/Walk to Beach for 2 or more!
A patio with Adirondack chairs, a fire pit, and a wooden deck.

11. Samara Tide | 3BR Walk to Bay Beach, Pet Friendly

Samara Tide | 3BR Walk to Bay Beach, Pet Friendly
Eastham
10.0 out of 10, Exceptional, (1 review)
"Nice quiet family-friendly location. Very clean property with all the essential move-in ready provisions provided. All communication was very clear and informative. Highly recommend."
United States
Pete P.
The price is €446
includes taxes & fees
29 Sept - 30 Sept
Samara Tide | 3BR Walk to Bay Beach, Pet Friendly
A room with a blue sofa, wicker chairs, a round table, a wall-mounted lamp, and a glass door leading outside.

12. 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, (105 reviews)
"Our second year in a row staying here. Cute house and great location! "
United States
Erin M.
The price is €555
includes taxes & fees
29 Sept - 30 Sept
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK
An outdoor deck with a grill, dining table, chairs, and an umbrella.

13. 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 €513
includes taxes & fees
30 Sept - 1 Oct
Sleeps 2-8/Soaking Tub/FirePit~Burrows
A modern kitchen with white cabinetry, a stainless steel refrigerator, and a central island with bar stools.

14. 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)
The price is €844
includes taxes & fees
6 Sept - 7 Sept
2021 CONSTRUCTION 3BR 3BA. Close to Bike Trail & Beaches. Central AC, Firepit.
A sliding glass door leading to an outdoor patio with a view of a lake, red and beige outdoor furniture, and a fire pit.

15. 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)
"Beautiful spot ! House was clean and well equipped. "
United States
Cynthia P.
The price is €552
includes taxes & fees
28 Sept - 29 Sept
Pond House~Waterfront Oasis on Minister's Pond
A living room with a fireplace, sofas, a TV, and a bookshelf.

16. 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 €599
includes taxes & fees
8 Sept - 9 Sept
Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail
A beach with footprints, a large rock, and a clear sky.

17. 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 €647
includes taxes & fees
28 Sept - 29 Sept
The Brewster Pearl
A living room with a sectional sofa, a fireplace, a flat-screen TV, and a dining area.

18. New! Sandy Point-Private beach/Dog Friendly

New! Sandy Point-Private beach/Dog Friendly
Eastham
10.0 out of 10, Exceptional, (1 review)
"The little touches included with this listing are what makes the difference between returning to a “house we rented” and returning to a “home away from home”. Thoughtful items like nightlights, labeled light switches (so easy but so useful), and motion sensing lights on the outdoor deck stairs for when you were out later than expected and forgot to leave the outside lights on. The kitchen is well stocked with pots, pans, and all manner of cooking gear. WiFi was super fast all throughout the...
United States
Matthew and Kym P.
The price is €620
includes taxes & fees
8 Sept - 9 Sept
New! Sandy Point-Private beach/Dog Friendly
A dining table set for six with placemats, plates, cutlery, and glasses. There are two benches at each end of the table.

19. Beau Breeze~3b/2b by Cooks Brook Beach/Dog Too!

Beau Breeze~3b/2b by Cooks Brook Beach/Dog Too!
Eastham
9.8 out of 10, Exceptional, (6 reviews)
"The home was clean, cool and comfortable. Booking was easy and effortless! Can’t wait to go back!"
United States
Kim S.
The price is €547
includes taxes & fees
23 Sept - 24 Sept
Beau Breeze~3b/2b by Cooks Brook Beach/Dog Too!
A table set for two with a view of the sunset over the water, outdoor seating, and a grill area.

20. Mazi's-A Waterfront/2 Bd/Dog Friendly Oasis for 4

Mazi's-A Waterfront/2 Bd/Dog Friendly Oasis for 4
Eastham
10.0 out of 10, Exceptional, (1 review)
"Just perfect all around!"
United States
Alexis N.
The price is €810
includes taxes & fees
4 Sept - 5 Sept
Mazi's-A Waterfront/2 Bd/Dog Friendly Oasis for 4
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

Cape Sands Inn

Cape Sands Inn

10/10 Excellent
"The cape sands inn was the best choice for our stay! Centrally located, they have everything you could need. The pools were amazing! Staff was friendly enough despite their limited staffing. The fire pit was a true highlight! We even extended our stay an extra night because the only thing we missed during our trip was just a relaxing day at the motel!"
Tammy 3-night trip
Posted 7 hours ago
Cape Sands Inn

Find out more about Orleans

Orleans Holiday Homes information

Number of reviews
338
Accommodation
2604 Holiday Homes
Lowest Price
€430
Highest Price
€2,883