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

Orleans Vacation Rentals

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Check prices for these dates

In two weeks
Oct 16 - Oct 18
In two months
Nov 27 - Nov 29
In three months
Dec 25 - Dec 27
In four months
Jan 22 - Jan 24

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 $2,560
CA $4,462 total
includes taxes & fees
Oct 19 - Oct 20
Beautiful home in Orleans. Park, Beach, Lake & Ocean. Telsa charge
A row of white buildings with storefronts, including a visible sign for 'Chatham' and a 'Chatham' sign above a window.

2. 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 $198
CA $682 total
includes taxes & fees
Oct 7 - Oct 8
Lovely House 5 Min to Beach with Deck, Grill, Garage
A living room with a grey sofa, striped rug, and a lamp.

3. 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)
"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 CA $218
CA $723 total
includes taxes & fees
Oct 6 - Oct 7
The Pet-Friendly Surf Shack Hideaway on the Cove
A resort with a large pool, sun loungers, and a pier extending into the water.

4. 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 $199
CA $712 total
includes taxes & fees
Oct 7 - Oct 8
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.

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 $216
CA $720 total
includes taxes & fees
Oct 6 - Oct 7
National Seashore/Updated/Game Room~Blue Pearl
Living room with plenty of seating and beautiful coastal design

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 CA $273
CA $942 total
includes taxes & fees
Oct 6 - Oct 7
Solace in the Sun- Adj. Beds/Game Rm/Soakng Tub/Dog Ok
An outdoor deck with a grill, dining table, chairs, and an umbrella.

7. 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 $221
CA $745 total
includes taxes & fees
Oct 13 - Oct 14
Sleeps 2-8/Soaking Tub/FirePit~Burrows
A patio with Adirondack chairs, a fire pit, and a wooden deck.

8. 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 $210
CA $600 total
includes taxes & fees
Oct 6 - Oct 7
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.

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)
"Had everything we needed for a comfortable stay."
United States
BILL
The price is CA $223
CA $748 total
includes taxes & fees
Oct 6 - Oct 7
Pond House~Waterfront Oasis on Minister's Pond
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 CA $226
CA $752 total
includes taxes & fees
Oct 6 - Oct 7
The Alpine/Walk to Beach for 2 or more!
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 CA $283
CA $836 total
includes taxes & fees
Oct 12 - Oct 13
10 min walk to Beach - Home with Amazing View & Huge Deck
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
9.8 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 $135
CA $727 total
includes taxes & fees
Oct 27 - Oct 28
Quaint Chatham home w/beautiful backyard & furnished multi-level deck, dogs OK
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, (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 $221
CA $745 total
includes taxes & fees
Oct 13 - Oct 14
Beau Breeze~3b/2b by Cooks Brook Beach/Dog Too!
A beach with footprints, a large rock, and a clear sky.

14. 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 $306
CA $951 total
includes taxes & fees
Nov 1 - Nov 2
The Brewster Pearl
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, (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 $269
CA $808 total
includes taxes & fees
Oct 13 - Oct 14
Driftmoor~Dog Frndly 3bd/2 bth~Luxe
A wooden outdoor shed with a door, a window, and a gravel path leading to it.

16. 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 $277
CA $819 total
includes taxes & fees
Oct 6 - Oct 7
Gray Whale-Minutes to Eastham Bay & Ocean Beaches
A table set for two with a view of the sunset over the water, outdoor seating, and a grill area.

17. 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 CA $315
CA $700 total
includes taxes & fees
Oct 8 - Oct 9
Mazi's-A Waterfront/2 Bd/Dog Friendly Oasis for 4
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.

18. 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.
The price is CA $271
CA $1,082 total
includes taxes & fees
Oct 3 - Oct 4
Coastal Cape Cod 3 bedroom close to the beach, bike path & ponds!
A sandy beach with wooden posts and a clear view of the ocean.

19. 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 $326
CA $817 total
includes taxes & fees
Oct 20 - Oct 21
Sand Bar-Dog Friendly on Cooks Brook Beach
A modern kitchen with white cabinetry, a stainless steel refrigerator, and a central island with bar stools.

20. 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 $608
CA $1,446 total
includes taxes & fees
Oct 3 - Oct 4
2021 CONSTRUCTION 3BR 3BA. Close to Bike Trail & Beaches. Central AC, Firepit.
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

10/10 Excellent
"Loved the cottage! Beautiful view! Staff was lovely!"
Joanne 1-night trip
Posted less than an hour ago
Lighthouse Inn

Find out more about Orleans

Orleans Vacation Homes information

Number of reviews
320
Accommodation
2503 Vacation Homes
Lowest Price
CA $600
Highest Price
CA $4,462

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