Holiday Homes in Chatham

Change your mind

Book hotels with free cancellation

Treat yourself

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

Featured Holiday Homes in Chatham and around

Our top choices for Chatham holiday homes

"Plenty of space to stay with friends but have your own space. Lots of outdoors activities in the area which was perfect. Clean, comfortable and pool table and hot tub were a plus! "

"Great location for access to both Tanglewood and Lenox center. "

"We had a 2 night stay while in Catskill for a wedding. My hubby, 8 year old and 2 dogs in tow. House was just right for us. My son loved the board games available and the foosball table. House is uncluttered and very clean. Surrounding are is historic with a short walk to downtown shops. I would definitely rent here again. "

"What a wonderful property for our girls trip! The house is clean, there’s so much hangout space, and it’s so well supplied. "

"Fantastic home! Clean, well stocked and very comfortable. We had a great time and will be back. The owner was kind, considerate and appreciative of our stay. Thanks again! "

"Kind and responsive host."

includes taxes & fees

10 Sept - 11 Sept

"We had a great time staying at this house. It was quiet and relaxing. We would stay again!"

"We loved Manor Lane! It had every amenity you could ask for. The house is fun and charming and there are thoughtful touches everywhere you look! We had fun watching movies in the living room, playing games in the lounge, cooking family meals in the spectacular kitchen and playing tennis in the sunshine. A perfect 10!"

"Well located and comfortable "

"We thoroughly enjoyed our stay and would go again. The host was easy to communicate with and answered our questions quickly. Hope we get to take advantage of the pretty backyard next time. "

includes taxes & fees

3 Sept - 4 Sept

"Spacious, welcoming, so well stocked, we felt lucky to find the property."

"We went as a family to get away from the city life for the weekend. We have no complaints except that it could’ve been a bit cleaner in the sense that there were many cobwebs. Nonetheless we rlly enjoyed our weekend in Great Barrington "

"Enjoyed the property, location and charming house that was well stocked with everything we needed."

"Perfect for a family vacation with a baby and dog. Particularly enjoyed having drinks and dinner on the deck, overlooking the water. Felt like a private retreat. "

"Was as nice as the pictures. A plus for a very comfortable king sized bed! Right in town for walking to shops and restaurants. Thank you!"

"Clean, great communication with owner, excellent location! "

"This place truly has everything you could want in a vacation rental. It was exceptionally clean, spacious, and accommodating. From the moment we arrived, it felt like a home away from home. The host clearly puts a lot of care into maintaining the property and ensuring guests are comfortable. We had everything we needed for an enjoyable stay. Highly recommend and would definitely book again!"