Chatham, MA Vacation Homes from AED 1,135

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

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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 1,795 total

includes taxes & fees

27 Oct - 28 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

Corinne J.

AED 2,178 total

includes taxes & fees

23 Nov - 24 Nov

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 5,628 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 1,761 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.

An outdoor dining area with white chairs and umbrellas, overlooking the ocean.

7. 2 Bedroom, 2 Bath, 1100 sqft, sun porch, eat in kitchen, Washer/Dryer, Gas Grill

Dennis

Betsy D.

AED 1,135 total

includes taxes & fees

7 Nov - 8 Nov

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

8. 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

8 Nov - 9 Nov

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

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

Dennis Port

Art E.

AED 1,620 total

includes taxes & fees

26 Oct - 27 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.

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

West Brewster

Jim M.

AED 2,814 total

includes taxes & fees

27 Oct - 28 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.

AED 1,847 total

includes taxes & fees

2 Nov - 3 Nov

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

12. Family Cottage Close to Beach!!

Harwichport

John N.

AED 3,002 total

includes taxes & fees

26 Oct - 27 Oct

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

13. 10 min walk to Beach - Home with Amazing View & Huge Deck

Eastham

AED 1,888 total

includes taxes & fees

27 Oct - 28 Oct

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

14. Seaside Getaway - Harwichport Beachhouse

Harwich

Meredith R.

AED 1,699 total

includes taxes & fees

26 Oct - 27 Oct

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

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

Harwich

Nicole M.

AED 2,110 total

includes taxes & fees

24 Nov - 25 Nov

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

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

Eastham

Susan C.

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

17. Beach Walks, Books & Bay Sunsets

Brewster

Sandra G.

AED 2,350 total

includes taxes & fees

26 Oct - 27 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.

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

Dennis

Diana S.

AED 1,830 total

includes taxes & fees

2 Nov - 3 Nov

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

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

Eastham

Tereasa F.

AED 1,796 total

includes taxes & fees

28 Oct - 29 Oct

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Top Chatham Hotel Reviews

Sunbird Cape Cod Resort

8/10 Good

"Good sized clean room. Good location for exploring. Nice restaurants nearby. Even had a pickleball court with equipment provided. Staff were very helpful. Amazing whale watching with Dolphin Fleet, 37 whales some with calves!!"

Margaritaville Resort Cape Cod

8/10 Good

"Overall, the hotel and our room were lovely. There was a large event taking place during our stay, and a significant number of younger guests from the event were gathered throughout the public areas. While completely understandable, it did make it difficult for us to enjoy those spaces. Our only real disappointment was breakfast. We needed something quick and were directed to the to-go area, but waited more than 20 minutes for a simple breakfast sandwich. When it was made incorrectly, the interaction felt unnecessarily dismissive and we were made to feel as though the mistake was our fault. A little more customer-service-minded handling would have made a big difference. Aside from that experience, we had a lovely room and enjoyed our stay overall."

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

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