Photo by Julie Miller

Search Vacation Homes in Chestertown

Plan, book, stay with confidence

Be picky

Search almost a million properties worldwide

Treat yourself

Change your mind

Book hotels with free cancellation

Check prices for these dates

Next weekend

In two weeks

In one month

In two months

Compare 507 Vacation Homes in Chestertown with updated reviews, rates, and availability.

"We enjoyed our week stay with our family and 2 small dogs. Local beach is a convenient walk. Location is also convenient to Lake George attractions - we made the drive almost every day. Would definitely stay here again in the future."

"Super clean super nice people WiFi was a little tough but if you are looking for a great spot this is your place convenient to Lake George "

"We loved our stay. 67 steps is a fantastic property; quaint, bright, and peaceful. Kitchen was fully equipped, bedrooms were sparkling clean and beautifully furnished, and the house was warm and welcoming. We highly recommend this home."

"We wish we could have stayed longer! The house was wonderful and equipped with everything you could think of. Great area too!"

"I was pleasantly surprised by the house and we all enjoyed our time there! That being said, there were some minor details that I think are worth passing on for future guests to be aware of prior to their stay: -There were area rugs placed on top of the carpets in each room (totally understandable to protect high traffic areas!) however, they were laid out so poorly they bunched up all over and were like that for so long they were impossible to flatten out. This caused several trips and almost...

"We rented the main house and guest house for a ski trip with our kids and some of their college friends. Upon arrival, the place was spotless! There was plenty of room for sleeping and hanging out. Guest house was also perfect. Kitchen was well stocked. Gore mountain very close also convenient to supermarket and a few restaurants. Only minor issue was inconsistent water pressure which is not unusual in ski / lake houses like.this. Would definitely rent again "

"This was the perfect get away for spring brake. The place is gorgeous and is even more cozy that you could see in the pictures. The location is really nice. We had the most delicious BBQ in a place called Marks Hometown. There was also a craft beers spot with amazing beer. We went for a super short hike with our kids. The mountain is beautiful and incredibly close to this place. We absolutely loved this place! We’re already planning on coming back for the summer. PS. And the hot tub in beyond...

"Great location, everything needed in the home, and easy check in/out process. Thanks!"

"We loved our stay. The house is exactly as described and close to everything we had planned while in the area. Would definitely stay again. The host Dianne was wonderful."

"The home was amazing plenty of space for the whole family we all had a great stay at the home. The movie selection was great and was nice to unplug for a bit and watch movies with the family. The only problem I had was the road entering home is a bit challenging even with 4x4 the top portion was all ice and made almost impossible to climb but luckily neighbors were great and they had someone come sand within hour which fixed the issue. Will def stay again maybe summer next time if available "

"We had the absolute BEST weekend. We went skiing at Gore Mountain. We had friends and family and it fit us perfectly. We had so much fun in the game room and hot tub! This house is huge and absolutely beautiful. Would recommend to anyone 100%!!!"

"Had a wonderful stay at this property. Owner was friendly and readily available. Easy to get to and good proximity to ski area. "

AED 608 total

includes taxes & fees

26 Mar - 27 Mar

"Plenty of room for everyone, warm and relaxing."

"Wonderful stay. Owner very accomodating. We had everything we needed."

"Four of us stayed at this beautiful,private log cabin style home in the woods for the weekend.It was close to town if you needed gas,groceries,souvenir shopping,etc.,The large home was very neat,clean and comfortable.The owners left us a lovely greeting card for when we arrived.Beds were very comfortable.We highly recommend this home and would enjoy another stay there.Thank you."

"This was the coolest, cleanest, quirkiest, cutest, most fascinating vacation rental I’ve ever stayed in. I’m a sucked for a well equipped kitchen- this one had everything I could have wanted and more. The details of the house were exquisite, from a craftsmanship perspective and a storyteller’s perspective. The amenities were luxurious, from the beds and baths to the cedar soaking tub. The hosts were delightful. Not only do I want to come back, I wanted to buy the place. Such an experience!!"

AED 1,811 total

includes taxes & fees

26 Mar - 27 Mar

"We really enjoyed our week at Peaceful Moose house. The house is very cozy, with lots of space for our party of 6. The first floor master bedroom is so amazing, with a view of the lake. We enjoyed having coffee in the morning and drinks in the evening on the beautiful deck overlooking the lake. The kids enjoyed making smores on the firepit. Tony was a great host and went above and beyond for us. We miss Lake George and Peaceful Moose already and hope to be back!"