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
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

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)
"Great house, so much room! We enjoyed our stay!!"
United States
Gina M.
Beautiful home in Orleans. Park, Beach, Lake & Ocean. Telsa charge
A living room with a grey sofa, striped rug, and a lamp.

2. 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, (30 reviews)
"We had such a wonderful time at the Surf Shack. The location was perfect. Within 15 minutes the best beaches, best dining, best shopping..everything. The house was incredibly clean with all the amenities needed to have a great family vacation. The host was incredibly quick to reply to any and all inquiries and was so pleasant to deal with. We couldn’t be any happier with our stay and will definitely stay there again if our travels return us to the Cape."
United States
Justin R.
The price is €466
includes taxes & fees
27 Oct - 28 Oct
The Pet-Friendly Surf Shack Hideaway on the Cove
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, (4 reviews)
"Great house with comfy beds. Would consider staying again. "
United States
Susan C.
Lovely House 5 Min to Beach with Deck, Grill, Garage
An outdoor deck with a grill, dining table, chairs, and an umbrella.

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

Sleeps 2-8/Soaking Tub/FirePit~Burrows
Eastham
10.0 out of 10, Exceptional, (9 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 €483
includes taxes & fees
28 Oct - 29 Oct
Sleeps 2-8/Soaking Tub/FirePit~Burrows
Living room with plenty of seating and beautiful coastal design

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.
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.

6. 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.
Cozy Large Home in Harwich with Patio near Wequassett Resort
A dining table set with plates, glasses, and a variety of food including grapes, cheese, and crackers.

7. 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 €441
includes taxes & fees
19 Oct - 20 Oct
National Seashore/Updated/Game Room~Blue Pearl
A beach with a wooden fence and a clear view of the ocean.

8. 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 €476
includes taxes & fees
18 Oct - 19 Oct
The Alpine/Walk to Beach for 2 or more!
A patio with Adirondack chairs, a fire pit, and a wooden deck.

9. 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, (3 reviews)
"The house was cute and clean. The private beach was amazing. We enjoyed our stay!"
United States
Susan W.
The price is €397
includes taxes & fees
27 Oct - 28 Oct
Samara Tide | 3BR Walk to Bay Beach, Pet Friendly
A sliding glass door leading to an outdoor patio with a view of a lake, red and beige outdoor furniture, and a fire pit.

10. 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 €474
includes taxes & fees
19 Oct - 20 Oct
Pond House~Waterfront Oasis on Minister's Pond
A spacious living area with wooden floors, a large dining table, and multiple windows offering a view of the beach.

11. 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 €550
includes taxes & fees
5 Nov - 6 Nov
10 min walk to Beach - Home with Amazing View & Huge Deck
A beach with footprints, a large rock, and a clear sky.

12. The Brewster Pearl

The Brewster Pearl
Brewster
10.0 out of 10, Exceptional, (3 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
A dining table set for six with placemats, plates, cutlery, and glasses. There are two benches at each end of the table.

13. 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, (7 reviews)
"Clean well maintained"
United States
mark A.
The price is €473
includes taxes & fees
18 Oct - 19 Oct
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.

14. 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 €453
includes taxes & fees
28 Oct - 29 Oct
Mazi's-A Waterfront/2 Bd/Dog Friendly Oasis for 4
A wooden table set outdoors with plates, glasses, a bottle, and a metal container.

15. Driftmoor~Dog Frndly 3bd/2 bth~Luxe

Driftmoor~Dog Frndly 3bd/2 bth~Luxe
Eastham
10.0 out of 10, Exceptional, (3 reviews)
"Driftmoor was a fantastic place to stay for our Labor Day trip to Provincetown. The property is extremely clean and spacious. The location was convenient to several local eateries. Management was easy to communicate with."
United States
David
The price is €517
includes taxes & fees
28 Oct - 29 Oct
Driftmoor~Dog Frndly 3bd/2 bth~Luxe
A sandy beach with wooden posts and a clear view of the ocean.

16. Sand Bar~3 BR Dog Friendly Beachside Home

Sand Bar~3 BR Dog Friendly Beachside Home
Eastham
10.0 out of 10, Exceptional, (34 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 €478
includes taxes & fees
22 Oct - 23 Oct
Sand Bar~3 BR Dog Friendly Beachside Home
A room with a blue sofa, wicker chairs, a round table, a wall-mounted lamp, and a glass door leading outside.

17. 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, (107 reviews)
"Excellent location and stay at the lucky 7 cottage. The communication with the host was outstanding, best I’ve experienced. We’ll definitely be back for another time at this location."
United States
Mark K.
The price is €447
includes taxes & fees
27 Oct - 28 Oct
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK
A wooden outdoor shed with a door, a window, and a gravel path leading to it.

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

Gray Whale-Minutes to Eastham Bay & Ocean Beaches
Eastham
10.0 out of 10, Exceptional, (7 reviews)
"very well appointed accommodations - great location - helpful amenities. would come back again!"
United States
Leonard
The price is €516
includes taxes & fees
27 Oct - 28 Oct
Gray Whale-Minutes to Eastham Bay & Ocean Beaches
A spacious living room with a large sliding glass door leading to an outdoor patio, a ceiling fan, and a white sofa with patterned cushions.

19. Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!

Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!
West Brewster
10.0 out of 10, Exceptional, (37 reviews)
"Previous reviews were all 10/10 & I agree once again. We definitely will be back!!"
United States
Jim M.
Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!
A sandy beach path leading to the ocean with a clear sky.

20. Beach Walks, Books & Bay Sunsets

Beach Walks, Books & Bay Sunsets
Brewster
10.0 out of 10, Exceptional, (3 reviews)
"The property was very clean, lots of little excellent touches, and amazing views. We truly enjoyed the pathway to the private beach. I wished we could have stayed longer. We will definitely be booking again."
United States
Sandra G.
The price is €579
includes taxes & fees
19 Oct - 20 Oct
Beach Walks, Books & Bay Sunsets
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

Bayside Resort Hotel

Bayside Resort Hotel

10/10 Excellent
"A little dated but comfortable, clean and a good choice of breakfast. Lovely area outside to the rear of the Hotel and both pool areas were very nice. Absolutely perfect if travelling with children."
judith 3-night trip
Posted 1 hour ago
Bayside Resort Hotel

Find out more about Orleans

Orleans Holiday Homes information

Number of reviews
278
Accommodation
2541 Holiday Homes
Lowest Price
€397
Highest Price
€579