Orleans Vacation Homes

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

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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

Orleans

Darren Y.

HK$24,618 total

includes taxes & fees

19 Oct - 20 Oct

A living room with a grey sofa, striped rug, and a lamp.

2. The Pet-Friendly Surf Shack Hideaway on the Cove

Eastham

"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."

Justin R.

HK$4,044 total

includes taxes & fees

3 Nov - 4 Nov

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

Eastham

Susan C.

HK$3,695 total

includes taxes & fees

8 Oct - 9 Oct

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

Harwich

Bill F.

HK$3,763 total

includes taxes & fees

7 Oct - 8 Oct

An outdoor deck with a grill, dining table, chairs, and an umbrella.

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

Eastham

Lourdes P.

HK$4,091 total

includes taxes & fees

13 Oct - 14 Oct

A patio with Adirondack chairs, a fire pit, and a wooden deck.

6. Samara Tide | 3BR Walk to Bay Beach, Pet Friendly

Eastham

Susan W.

HK$3,295 total

includes taxes & fees

13 Oct - 14 Oct

Living room with plenty of seating and beautiful coastal design

7. Solace in the Sun- Adj. Beds/Game Rm/Soakng Tub/Dog Ok

Eastham

Donna R.

HK$5,152 total

includes taxes & fees

7 Oct - 8 Oct

A beach with a wooden fence and a clear view of the ocean.

8. The Alpine/Walk to Beach for 2 or more!

Eastham

Jennifer G.

HK$4,130 total

includes taxes & fees

7 Oct - 8 Oct

A dining table set with plates, glasses, and a variety of food including grapes, cheese, and crackers.

9. National Seashore/Updated/Game Room~Blue Pearl

Eastham

Catharine D.

HK$3,927 total

includes taxes & fees

7 Oct - 8 Oct

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

Eastham

BILL

HK$4,101 total

includes taxes & fees

8 Oct - 9 Oct

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

Eastham

HK$4,580 total

includes taxes & fees

12 Oct - 13 Oct

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

Chatham

Mark K.

HK$3,957 total

includes taxes & fees

13 Oct - 14 Oct

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!

Eastham

Kim S.

HK$4,091 total

includes taxes & fees

13 Oct - 14 Oct

A wooden table set outdoors with plates, glasses, a bottle, and a metal container.

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

Eastham

David

HK$4,402 total

includes taxes & fees

13 Oct - 14 Oct

A table set for two with a view of the sunset over the water, outdoor seating, and a grill area.

15. Mazi's-A Waterfront/2 Bd/Dog Friendly Oasis for 4

Eastham

Alexis N.

HK$3,915 total

includes taxes & fees

13 Oct - 14 Oct

A beach with footprints, a large rock, and a clear sky.

16. The Brewster Pearl

Brewster

"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...

PAULA

HK$5,236 total

includes taxes & fees

4 Nov - 5 Nov

A wooden outdoor shed with a door, a window, and a gravel path leading to it.

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

Eastham

Leonard

HK$4,490 total

includes taxes & fees

7 Oct - 8 Oct

A sandy beach with wooden posts and a clear view of the ocean.

18. Sand Bar-Dog Friendly on Cooks Brook Beach

Eastham

Debra H.

HK$4,450 total

includes taxes & fees

20 Oct - 21 Oct

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!

West Brewster

Jim M.

HK$6,242 total

includes taxes & fees

3 Nov - 4 Nov

A sandy beach path leading to the ocean with a clear sky.

20. Beach Walks, Books & Bay Sunsets

Brewster

Sandra G.

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Top Orleans Hotel Reviews

Sunbird Cape Cod Resort

10/10 Excellent

"Excellent stay. Very clean. Great staff. Convenient to everything. Would definitely stay again."

Cape Sands Inn

8/10 Good

"At this price point, Cape Sands Inn is excellent value. We stayed in room 212, which had a small, but useful balcony that looked out over the garden, barbeque area, and the creek. The room had 2 comfortable queen beds, a large fridge, a coffee maker, and everything worked. I had to ask reception to turn up the hot water, which they did - straight away. I had to learn that it was necessary to run the bath tub tap until the water got hot to get hot water from the sink tap. Once I understood what I had to do, it was easy. The cleaners did a good job, every 2 days. The reception staff were nice and very helpful. It was a very good experience :)"

Uncommoner Hotel by Reverie Boutique Collection

10/10 Excellent

"Loved the hotel and can’t speak more highly of the staff. Only disappointment was the restaurant and grounds were closed our second night due to a private function. Our first night was rained out so giving up our last night to a private party was unfortunate. Maybe in the future they will open some part of the property for hotel guests to enjoy while accommodating a private party."

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