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

Gina M.

HK$22,302 total

includes taxes & fees

15 Nov - 16 Nov

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

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

Eastham

Nancy S.

HK$3,622 total

includes taxes & fees

3 Nov - 4 Nov

A wooden deck with a ceiling fan, a sofa, and chairs.

3. Lovely House 5 Min to Beach with Deck, Grill, Garage

Eastham

Susan C.

HK$3,593 total

includes taxes & fees

3 Nov - 4 Nov

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

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

Eastham

Lourdes P.

HK$3,989 total

includes taxes & fees

8 Nov - 9 Nov

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

Eastham

Catharine D.

HK$3,792 total

includes taxes & fees

3 Nov - 4 Nov

Living room with plenty of seating and beautiful coastal design

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

Eastham

Donna R.

HK$4,720 total

includes taxes & fees

3 Nov - 4 Nov

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

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

Eastham

Pete P.

HK$3,160 total

includes taxes & fees

3 Nov - 4 Nov

A spacious living area with wooden floors, a large dining table, and multiple windows offering a view of the beach.

8. 10 min walk to Beach - Home with Amazing View & Huge Deck

Eastham

HK$4,561 total

includes taxes & fees

18 Nov - 19 Nov

A living room with a fireplace, a sofa, a coffee table, and a television.

9. 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$4,929 total

includes taxes & fees

3 Nov - 4 Nov

A kitchen with granite countertops, white cabinets, and a dining area with a table set for two.

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

Eastham

Jennifer G.

HK$3,959 total

includes taxes & fees

3 Nov - 4 Nov

A sliding glass door leading to an outdoor patio with a view of a lake, red and beige outdoor furniture, and a fire pit.

11. Pond House~Waterfront Oasis on Minister's Pond

Eastham

BILL

HK$3,789 total

includes taxes & fees

3 Nov - 4 Nov

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

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

Eastham

Tereasa F.

HK$3,629 total

includes taxes & fees

4 Nov - 5 Nov

A cozy room with a wooden ceiling, a striped sofa, a beige sofa, a wooden coffee table, and a view of the outdoors through large windows.

13. Sand Bar~3 BR Dog Friendly Beachside Home

Eastham

Debra H.

HK$3,746 total

includes taxes & fees

3 Nov - 4 Nov

A dining area with a table set for two, a chair, and a plant with pink flowers.

14. Beach Walks, Books & Bay Sunsets

Brewster

Sandra G.

HK$4,277 total

includes taxes & fees

3 Nov - 4 Nov

A dining table set for six with placemats, plates, cutlery, and glasses. There are two benches at each end of the table.

15. Beau Breeze~3b/2b by Cooks Brook Beach/Dog Too!

Eastham

mark A.

HK$4,037 total

includes taxes & fees

3 Nov - 4 Nov

A room with a blue sofa, wicker chairs, a round table, a wall-mounted lamp, and a glass door leading outside.

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

Chatham

Mark K.

HK$4,235 total

includes taxes & fees

3 Nov - 4 Nov

A wooden deck with a table and chairs, an umbrella, and a view of the sea.

17. Spectacular Bayfront Cottage with Private Deck & Sunset Views

Wellfleet

Scott M.

HK$3,897 total

includes taxes & fees

29 Nov - 30 Nov

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

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

Eastham

David

HK$4,743 total

includes taxes & fees

15 Nov - 16 Nov

A modern kitchen with white cabinetry, a stainless steel refrigerator, and a central island with bar stools.

19. 2021 CONSTRUCTION 3BR 3BA. Close to Bike Trail & Beaches. Central AC, Firepit.

Eastham

Mark T R.

HK$7,232 total

includes taxes & fees

3 Nov - 4 Nov

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.

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

West Brewster

Jim M.

HK$5,696 total

includes taxes & fees

3 Nov - 4 Nov

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Top Orleans Hotel Reviews

Cape Sands Inn

10/10 Excellent

"Very good"

Red Jacket Beach Resort

8/10 Good

"Great little spot I stayed at for work on my way to Nantucket. It’s been lightly updated but could use more of an update, particularly the bathrooms and wooden decks leading to the rooms. . The rooms were nice with AMAZING views out both the front door and balcony. The property was kept very neat."

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