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Vacation Homes in Chatham

Our top choices for Chatham vacation homes

"Stayed here for a weekend with my fiance and our dog and it was perfect. Short 5 minute drive from downtown and all the great restaurants and shopping. Very dog friendly with fenced in backyard. "

SAR 1,975 total

includes taxes & fees

2 Sep - 3 Sep

"Pam was an excellent host. The house is in a great location and served as a perfect home base for my group over 4th of July Weekend."

SAR 2,693 total

includes taxes & fees

3 Sep - 4 Sep

"Great location, very sweet house. Perfect for our weekend getaway."

SAR 2,280 total

includes taxes & fees

7 Sep - 8 Sep

"Loved our stay. Property is very clean and in a quiet neighborhood close to town and beaches. Host Bonnie was great. Would definitely rent again."

SAR 1,855 total

includes taxes & fees

1 Sep - 2 Sep

"We had a lovely time celebrating my wife’s 60th birthday at this beautiful Chatham property. The house fit four generations perfectly, with great spaces to gather, nearby beach access, and a fun swing set for the little ones. The Chatham Bars Inn, where we ate and played tennis, is in easy walking distance. Bill, the property manager, was very responsive. "

SAR 10,162 total

includes taxes & fees

1 Sep - 2 Sep

"Walk to all the shops and beaches. Quiet neighborhood, yet still in the heart of a beautiful Cape Cod home. Large table on a pretty porch that sits 12 people comfortably. Nice back yard. Very clean. Bill, the owner, was very responsive. You will enjoy your stay here!!"

SAR 7,000 total

includes taxes & fees

22 Sep - 23 Sep

SAR 2,011 total

includes taxes & fees

29 Sep - 30 Sep

"The property was perfect. Fenced in large back yard, quiet neighborhood, centrally located to everythjng. House was clean & neat neat "

SAR 1,517 total

includes taxes & fees

29 Sep - 30 Sep

"Recommended "

"Fifth year we vacation at the Cape.This was the beat place we had.Our host Tara was great.Always got right back to me with a response.The house was clean,it was very comfortable,and very well stocked.We will definitely stay there again."

SAR 2,142 total

includes taxes & fees

29 Sep - 30 Sep

"Cosy retreat with pond view. Great for canoeing with the dog. Sweet porch for reading and morning coffee. Tara was an excellent host who communicated immediately and went well above and beyond to correct an issue that was out of her control.A great central location that allowed us to roam freely to our favorite beaches, hikes, and restaurants. We will gladly return in the future. "

SAR 1,372 total

includes taxes & fees

1 Sep - 2 Sep

"We’d loved our stay. Great house in a great neighborhood. Would love to stay here again!"

SAR 3,023 total

includes taxes & fees

23 Sep - 24 Sep

"Very cute and comfortable 3-bedroom home. The kitchen is nice and big and very well stocked. We enjoyed the large deck."

SAR 1,876 total

includes taxes & fees

3 Sep - 4 Sep

"The home was clean, cool and comfortable. Booking was easy and effortless! Can’t wait to go back!"

SAR 2,203 total

includes taxes & fees

29 Sep - 30 Sep

"This house worked perfectly for two families vacationing together. The lower level provided a great hang out space for the teens. This home has recently been renovated and has new floors, appliances, and very comfortable beds. It was very clean and nicely decorated.We loved the proximity to the bike path - and the location was the perfect distance to bike into Orleans for a visit to The Chocolate Sparrow, or to head in the other direction to swim at Great Pond, or take the bike trail out to...

SAR 3,052 total

includes taxes & fees

1 Sep - 2 Sep

2 bedrooms, desk, iron/ironing board, WiFi

"The property met our needs very nicely. The bathrooms were dated, as was he most of the home, but it was clean and very comfortable. We enjoyed staying there very much."

SAR 1,718 total

includes taxes & fees

29 Sep - 30 Sep