Orleans Holiday Homes from £322: Search Holiday Homes in Orleans

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.

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

Anna P.

includes taxes & fees

29 Sept - 30 Sept

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.

includes taxes & fees

19 Oct - 20 Oct

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

Eastham

Donna R.

includes taxes & fees

29 Sept - 30 Sept

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.

includes taxes & fees

29 Sept - 30 Sept

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

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

Eastham

Jennifer G.

includes taxes & fees

29 Sept - 30 Sept

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

Eastham

BILL

includes taxes & fees

6 Oct - 7 Oct

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

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

Eastham

Lourdes P.

includes taxes & fees

28 Sept - 29 Sept

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

Eastham

includes taxes & fees

27 Sept - 28 Sept

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

Harwich

Bill F.

includes taxes & fees

28 Sept - 29 Sept

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

Eastham

Leonard

includes taxes & fees

29 Sept - 30 Sept

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

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

Eastham

Susan W.

includes taxes & fees

6 Oct - 7 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.

includes taxes & fees

6 Oct - 7 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.

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

West Brewster

Jim M.

includes taxes & fees

28 Sept - 29 Sept

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

15. Beach Walks, Books & Bay Sunsets

Brewster

Sandra G.

includes taxes & fees

6 Oct - 7 Oct

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

16. Sand Bar-Dog Friendly on Cooks Brook Beach

Eastham

Debra H.

includes taxes & fees

29 Sept - 30 Sept

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

Chatham

Mark K.

includes taxes & fees

5 Oct - 6 Oct

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.

Eastham

Mark T R.

includes taxes & fees

25 Sept - 26 Sept

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

19. 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

includes taxes & fees

25 Oct - 26 Oct

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

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

Eastham

David

includes taxes & fees

20 Oct - 21 Oct

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Top Orleans Hotel Reviews

Hyannis Harbor Hotel

10/10 Excellent

"Lovely hotel great location and staff was excellent"

Uncommoner Hotel by Reverie Boutique Collection

8/10 Good

"It was a nice touch to get a complementary champagne on arrival The bathroom, shower pumps for the shampoo and for the shower gel did not work. I asked twice in one day for it to be fixed and it was not I asked the second day one time and it was not fixed. The third day I told the front desk that I was just gonna post that this is my fourth time asking and it hasn’t been fixed and it was an easy fix. He said he would take care of it and he did. But seriously, three other staff members could not get a new pump? The properties beautiful and has a lot of amenities. Unfortunately, it rained one day so we had to stay in the hotel and just watch TV and read books."