Chatham, MA Vacation Homes from AED 1,592

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 vacation 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.

AED 1,778 total

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.

AED 2,026 total

includes taxes & fees

21 Oct - 22 Oct

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

3. Beautiful home near Jacknife Beach and bike trail

Chatham

Claire D.

AED 2,257 total

includes taxes & fees

1 Nov - 2 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.

AED 5,498 total

includes taxes & fees

26 Oct - 27 Oct

A resort with a large pool, sun loungers, and a pier extending into the water.

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

Harwich

Bill F.

AED 1,827 total

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.

AED 2,241 total

includes taxes & fees

20 Oct - 21 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

AED 2,463 total

includes taxes & fees

3 Nov - 4 Nov

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

8. Family Cottage Close to Beach!!

Harwichport

John N.

AED 3,002 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.

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

West Brewster

Jim M.

AED 2,697 total

includes taxes & fees

20 Oct - 21 Oct

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

10. 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.

AED 1,860 total

includes taxes & fees

26 Oct - 27 Oct

A bedroom with a bed, a desk, a chair, a TV, and a window.

11. Harwich Port Hideaway: 3-bedroom pet-friendly house with AC for relaxing stays

Harwich

Nicole M.

AED 1,934 total

includes taxes & fees

21 Oct - 22 Oct

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

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

Dennis Port

Art E.

AED 1,592 total

includes taxes & fees

20 Oct - 21 Oct

A wicker chair, a wicker table with a glass of water, a bottle of lemonade, a plate with watermelon slices, and a basket of bread rolls.

13. The Genoa | Your Perfect Dennis Port Beach Escape

Dennis Port

AED 1,707 total

includes taxes & fees

20 Oct - 21 Oct

A row of white buildings with storefronts, including a visible sign for 'Chatham' and a 'Chatham' sign above a window.

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

Eastham

Susan C.

AED 1,689 total

includes taxes & fees

20 Oct - 21 Oct

A beach with a wooden walkway leading to the shore, a rocky breakwater, and a clear sky at sunset.

15. Seaside Getaway - Harwichport Beachhouse

Harwich

Meredith R.

AED 1,699 total

includes taxes & fees

20 Oct - 21 Oct

A room with a wooden piano, a round mirror, a white door leading to a balcony with a view of greenery, and a hanging light fixture.

16. Gorgeous Home 1 mile to Beach, by Cape Cod Bikepath

Dennis

AED 1,830 total

includes taxes & fees

2 Nov - 3 Nov

A modern two-story building with large windows and a flat roof.

17. Walk 2 Beach! Slps 10! Fire Pit! Location! A/C!

Dennis Port

Jason H.

AED 2,542 total

includes taxes & fees

20 Oct - 21 Oct

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

18. 10 min walk to Beach - Home with Amazing View & Huge Deck

Eastham

AED 1,961 total

includes taxes & fees

27 Oct - 28 Oct

Living room with plenty of seating and beautiful coastal design

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

Eastham

Donna R.

AED 2,441 total

includes taxes & fees

26 Oct - 27 Oct

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

20. Beach Walks, Books & Bay Sunsets

Brewster

Sandra G.

AED 2,350 total

includes taxes & fees

20 Oct - 21 Oct

View all properties

Find vacation rentals that suit your style

Private vacation homes

Apartments

Save an average of 15% on thousands of hotels when you're signed in

Top Chatham Hotel Reviews

Cape Sands Inn

10/10 Excellent

"We enjoyed our stay. The sitting area and fore pit were nice. The staff were friendly and we enjoyed the hot tub. The pool area could be updated. Overall, great stay."

Lighthouse Inn

10/10 Excellent

"We were on a girl's trip, headed to Salem. Decided to come in a day early to visit Cape cod. We were so happy that we did. From the amazing staff, management, amenities and of course the cottage, everything was perfect. I can't even describe how delicious the food was and the variety of selections on the menu was outstanding. This is a beautiful property and we look forward to coming back with our husbands."

Chatham Wayside Inn

10/10 Excellent

"Great location! Right in the heart of downtown Chatham. The restaurant was a bonus with standard Cape Cod cuisine and very yummy. They also provide bikes if you want to pedal around town. The breakfast included was a bit light, but there's a perfect Cafe next door. We'll definitely stay there again."

Old Harbor Inn

10/10 Excellent

"We thoroughly enjoyed or 25th anniversary weekend at the Old Harbor inn! The staff and owner’s were amazing. The inn was well maintained the atmosphere and amenities were on point. The room was super and clean. The breakfast was great. Thanks to all who made our stay very enjoyable! We will be recommending this inn to our friends."

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Chatham vacation homes

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

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

3. Beautiful home near Jacknife Beach and bike trail

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

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