Chatham Holiday Houses | Expedia.co.nz

A boat on a calm river, a large house with a red roof, and dense greenery in the background.

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Chatham holiday homes

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

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

Chatham

Mark K.

includes taxes & fees

20 Oct - 21 Oct

A lighthouse with a cylindrical tower and a white building with a red roof.

2. Quaint & Cozy Downtown Chatham Home, Walk to Town and Beaches

Chatham

Joanne B.

includes taxes & fees

2 Nov - 3 Nov

A sandy beach with a grassy path leading to the water.

3. Beautiful home near Jacknife Beach and bike trail

Chatham

Claire D.

includes taxes & fees

13 Nov - 14 Nov

A two-story house with a covered porch and a stone staircase leading to the entrance.

4. Stunning Beach Retreat - Walk to Beach - Chatham Bars Inn - Town + Game Room

Chatham

Sally S.

includes taxes & fees

19 Oct - 20 Oct

A living room with two beige sofas, a white coffee table, a flat-screen TV, and a wicker basket.

5. Cozy Large Home in Harwich with Patio near Wequassett Resort

Harwich

Bill F.

includes taxes & fees

27 Oct - 28 Oct

An outdoor patio with Adirondack chairs, a fire pit, and string lights.

6. Winter Cape Escape - Walk to Wychmere, Fire Pit, Fenced Yard

Harwich

Norman Y.

includes taxes & fees

15 Oct - 16 Oct

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

7. 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

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.

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

West Brewster

Jim M.

includes taxes & fees

15 Oct - 16 Oct

A two-story house with a front porch, a chimney, and a well-maintained lawn.

9. Family Cottage Close to Beach!!

Harwichport

John N.

includes taxes & fees

26 Oct - 27 Oct

A wooden deck with outdoor furniture, a covered seating area, and a view of neighboring houses.

10. Family-friendly house w/gas grill, deck, streaming services - near Haigis Beach

Dennis Port

Art E.

includes taxes & fees

15 Oct - 16 Oct

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

11. 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.

includes taxes & fees

26 Oct - 27 Oct