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
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

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 NZ$5,574
includes taxes & fees
10 Sept - 11 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.
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, (4 reviews)
"Great house with comfy beds. Would consider staying again. "
United States
Susan C.
The price is NZ$859
includes taxes & fees
30 Sept - 1 Oct
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 NZ$894
includes taxes & fees
7 Oct - 8 Oct
The Pet-Friendly Surf Shack Hideaway on the Cove
Smart TV

5. 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$1,129
includes taxes & fees
28 Sept - 29 Sept
Solace in the Sun- Adj. Beds/Game Rm/Soakng Tub/Dog Ok
Dining

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 NZ$858
includes taxes & fees
7 Oct - 8 Oct
National Seashore/Updated/Game Room~Blue Pearl
Beach nearby

7. 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$914
includes taxes & fees
7 Oct - 8 Oct
The Alpine/Walk to Beach for 2 or more!
Pool

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)
"Great host. Convenient location for a visit to Chatham."
United States
Bill F.
The price is NZ$843
includes taxes & fees
28 Sept - 29 Sept
Cozy Large Home in Harwich with Patio near Wequassett Resort
Interior

9. 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 NZ$928
includes taxes & fees
6 Oct - 7 Oct
Pond House~Waterfront Oasis on Minister's Pond
TV, fireplace, books

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

10 min walk to Beach - Home with Amazing View & Huge Deck
Eastham
10 min walk to Beach - Home with Amazing View & Huge Deck
Sun-loungers, beach towels

11. 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 Brewster Pearl
TV, fireplace

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.
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK
Property grounds

13. 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.
Samara Tide | 3BR Walk to Bay Beach, Pet Friendly
Property grounds

14. 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$996
includes taxes & fees
7 Oct - 8 Oct
Gray Whale-Minutes to Eastham Bay & Ocean Beaches
Coffee/tea maker, fridge, microwave, oven

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$1,699
includes taxes & fees
10 Sept - 11 Sept
2021 CONSTRUCTION 3BR 3BA. Close to Bike Trail & Beaches. Central AC, Firepit.
Outdoor dining

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

Sleeps 2-8/Soaking Tub/FirePit~Burrows
Eastham
10.0 out of 10, Exceptional, (8 reviews)
"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 NZ$923
includes taxes & fees
1 Oct - 2 Oct
Sleeps 2-8/Soaking Tub/FirePit~Burrows
Dining

17. 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 NZ$867
includes taxes & fees
7 Oct - 8 Oct
Beau Breeze~3b/2b by Cooks Brook Beach/Dog Too!
Sun-loungers, beach towels

18. Beautiful home near Jacknife Beach and bike trail

Beautiful home near Jacknife Beach and bike trail
Chatham
9.8 out of 10, Exceptional, (87 reviews)
"This is second time to stay here! We love the location and hospitality of the hosts! Great place!"
United States
Barbara P.
The price is NZ$1,026
includes taxes & fees
5 Oct - 6 Oct
Beautiful home near Jacknife Beach and bike trail
TV, offices

19. 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$1,157
includes taxes & fees
22 Sept - 23 Sept
Cheery house with deck, sunroom & patio - short walk to pond, beach & Rail Trail
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 NZ$1,037
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.
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Top Orleans Hotel Reviews

Lighthouse Inn

Lighthouse Inn

8/10 Good
"was good!"
Dennis A 2-night trip
Posted less than an hour ago
Lighthouse Inn

Find out more about Orleans

Orleans Holiday Homes information

Number of reviews
312
Accommodation
2542 Holiday Homes
Lowest Price
NZ$843
Highest Price
NZ$5,574