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

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

Our top choices for Orleans vacation 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 CA $2,526
CA $4,402 total
includes taxes & fees
Oct 19 - Oct 20
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, (28 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 CA $214
CA $711 total
includes taxes & fees
Sep 30 - Oct 1
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.
The price is CA $209
CA $692 total
includes taxes & fees
Oct 19 - Oct 20
Lovely House 5 Min to Beach with Deck, Grill, Garage

4. 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 CA $268
CA $869 total
includes taxes & fees
Oct 7 - Oct 8
Solace in the Sun- Adj. Beds/Game Rm/Soakng Tub/Dog Ok
A dining table set with plates, glasses, and a charcuterie board with cheese, grapes, and crackers.

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 CA $213
CA $708 total
includes taxes & fees
Sep 30 - Oct 1
National Seashore/Updated/Game Room~Blue Pearl
A beach with a wooden fence and a clear view of the ocean.

6. 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 CA $222
CA $739 total
includes taxes & fees
Sep 30 - Oct 1
The Alpine/Walk to Beach for 2 or more!
A sliding glass door leading to an outdoor patio with a view of a lake, red and beige outdoor furniture, and a fire pit.

7. 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 CA $220
CA $738 total
includes taxes & fees
Oct 5 - Oct 6
Pond House~Waterfront Oasis on Minister's Pond
An outdoor deck with a grill, dining table, chairs, and an umbrella.

8. 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 CA $217
CA $732 total
includes taxes & fees
Sep 30 - Oct 1
Sleeps 2-8/Soaking Tub/FirePit~Burrows
A spacious living area with wooden floors, a large dining table, and multiple windows offering a view of the beach.

9. 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 CA $278
CA $821 total
includes taxes & fees
Oct 12 - Oct 13
10 min walk to Beach - Home with Amazing View & Huge Deck
A resort with a large pool, sun loungers, and a pier extending into the water.

10. 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 CA $209
CA $710 total
includes taxes & fees
Sep 28 - Sep 29
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.

11. 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 CA $273
CA $805 total
includes taxes & fees
Sep 30 - Oct 1
Gray Whale-Minutes to Eastham Bay & Ocean Beaches
A sandy beach path leading to the ocean with a clear sky.

12. Beach Walks, Books & Bay Sunsets

Beach Walks, Books & Bay Sunsets
Brewster
10.0 out of 10, Exceptional, (1 review)
"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 CA $271
CA $808 total
includes taxes & fees
Sep 23 - Sep 24
Beach Walks, Books & Bay Sunsets
A patio with Adirondack chairs, a fire pit, and a wooden deck.

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.
The price is CA $207
CA $592 total
includes taxes & fees
Oct 5 - Oct 6
Samara Tide | 3BR Walk to Bay Beach, Pet Friendly
A dining table set for six with placemats, plates, cutlery, and glasses. There are two benches at each end of the table.

14. 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 CA $218
CA $735 total
includes taxes & fees
Oct 5 - Oct 6
Beau Breeze~3b/2b by Cooks Brook Beach/Dog Too!
A sandy beach with wooden posts and a clear view of the ocean.

15. 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 CA $257
CA $731 total
includes taxes & fees
Sep 28 - Sep 29
Sand Bar-Dog Friendly on Cooks Brook Beach
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.

16. 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, (33 reviews)
"Previous reviews were all 10/10 & I agree once again. We definitely will be back!!"
United States
Jim M.
The price is CA $279
CA $1,098 total
includes taxes & fees
Sep 23 - Sep 24
Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!
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
9.8 out of 10, Exceptional, (106 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 CA $133
CA $717 total
includes taxes & fees
Oct 5 - Oct 6
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK
A modern kitchen with white cabinetry, a stainless steel refrigerator, and a central island with bar stools.

18. 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, (48 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 CA $598
CA $1,422 total
includes taxes & fees
Sep 27 - Sep 28
2021 CONSTRUCTION 3BR 3BA. Close to Bike Trail & Beaches. Central AC, Firepit.
A beach with footprints, a large rock, and a clear sky.

19. 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 CA $302
CA $932 total
includes taxes & fees
Oct 22 - Oct 23
The Brewster Pearl
A wooden table set outdoors with plates, glasses, a bottle, and a metal container.

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

Driftmoor~Dog Frndly 3bd/2 bth~Luxe
Eastham
10.0 out of 10, Exceptional, (2 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 CA $312
CA $858 total
includes taxes & fees
Oct 19 - Oct 20
Driftmoor~Dog Frndly 3bd/2 bth~Luxe
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

Hyannis Travel Inn

Hyannis Travel Inn

10/10 Excellent
"This is a nice hotel , excellent staff clean room well take care of good environment the best in Hyannis Massachusetts number 1"
Jerome 1-night trip
Posted less than an hour ago
Hyannis Travel Inn

Find out more about Orleans

Orleans Vacation Homes information

Number of reviews
316
Accommodation
2556 Vacation Homes
Lowest Price
CA $592
Highest Price
CA $4,402

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