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

Holiday Homes in Orleans

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
18 Sept - 20 Sept
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Orleans holiday homes

Dining

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 AU$4,619
includes taxes & fees
3 Sept - 4 Sept
Beautiful home in Orleans. Park, Beach, Lake & Ocean. Telsa charge
Outdoor dining

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 AU$955
includes taxes & fees
20 Sept - 21 Sept
Great for Families! Brewster Home 6 Mi to Beach
Exterior

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 AU$680
includes taxes & fees
28 Sept - 29 Sept
Lovely House 5 Min to Beach with Deck, Grill, Garage
Smart TV, fireplace

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, (27 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 AU$776
includes taxes & fees
30 Sept - 1 Oct
The Pet-Friendly Surf Shack Hideaway on the Cove
Dining

5. 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 AU$749
includes taxes & fees
29 Sept - 30 Sept
National Seashore/Updated/Game Room~Blue Pearl
Smart TV

6. 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 AU$968
includes taxes & fees
29 Sept - 30 Sept
Solace in the Sun- Adj. Beds/Game Rm/Soakng Tub/Dog Ok
Pool

7. 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 AU$689
includes taxes & fees
28 Sept - 29 Sept
Cozy Large Home in Harwich with Patio near Wequassett Resort
Property grounds

8. 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 AU$814
includes taxes & fees
29 Sept - 30 Sept
Gray Whale-Minutes to Eastham Bay & Ocean Beaches
Beach nearby

9. 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 AU$833
includes taxes & fees
30 Sept - 1 Oct
The Alpine/Walk to Beach for 2 or more!
Outdoor dining

10. 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 AU$798
includes taxes & fees
1 Oct - 2 Oct
Sleeps 2-8/Soaking Tub/FirePit~Burrows
Interior

11. 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 AU$861
includes taxes & fees
28 Sept - 29 Sept
Pond House~Waterfront Oasis on Minister's Pond
Coffee/tea maker, fridge, microwave, oven

12. 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 AU$1,343
includes taxes & fees
6 Sept - 7 Sept
2021 CONSTRUCTION 3BR 3BA. Close to Bike Trail & Beaches. Central AC, Firepit.
TV, offices

13. 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 AU$925
includes taxes & fees
8 Sept - 9 Sept
Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail
TV, fireplace

14. 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 AU$810
includes taxes & fees
29 Sept - 30 Sept
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK
Property grounds

15. 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, (2 reviews)
"The house was cute and clean. The private beach was amazing. We enjoyed our stay!"
United States
Susan W.
The price is AU$701
includes taxes & fees
8 Sept - 9 Sept
Samara Tide | 3BR Walk to Bay Beach, Pet Friendly
TV, fireplace, books

16. 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 AU$875
includes taxes & fees
28 Sept - 29 Sept
10 min walk to Beach - Home with Amazing View & Huge Deck
Sun-loungers, beach towels

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 AU$973
includes taxes & fees
30 Sept - 1 Oct
The Brewster Pearl
Dining

18. 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 AU$867
includes taxes & fees
23 Sept - 24 Sept
Beau Breeze~3b/2b by Cooks Brook Beach/Dog Too!
Beach nearby

19. Beach Walks, Books & Bay Sunsets

Beach Walks, Books & Bay Sunsets
Brewster
The price is AU$909
includes taxes & fees
30 Sept - 1 Oct
Beach Walks, Books & Bay Sunsets
On the beach

20. Sand Bar-Dog Friendly on Cooks Brook Beach

Sand Bar-Dog Friendly on Cooks Brook Beach
Eastham
10.0 out of 10, Exceptional, (33 reviews)
"We had a lovely visit with access to the beach and very comfortable beds. Enjoyed a beautiful sunset!"
United States
Debra H.
The price is AU$910
includes taxes & fees
1 Oct - 2 Oct
Sand Bar-Dog Friendly on Cooks Brook Beach
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Orleans Hotel Reviews

Cape Sands Inn

Cape Sands Inn

10/10 Excellent
"Room and view of the water was nice! Great location close to main attractions."
Andrea 2-night trip
Posted 6 hours ago
Cape Sands Inn

Find out more about Orleans

Orleans Holiday Homes information

Number of reviews
311
Accommodation
2561 Holiday Homes
Lowest Price
AU$680
Highest Price
AU$4,619