Chester Vacation Rentals

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 one month

In two months

In three months

Browse Select Chester Vacation Homes

"Condo was clean & well furnished. Only stayed one night after a visit to Quechee, Woodstock, and area."

CA $237 total

includes taxes & fees

Aug 24 - Aug 25

Iron/ironing board, travel crib, WiFi, bed sheets

"The property is exactly as represented. It’s super clean. Comfortable beds. Bathrooms are updated and nice. It’s right across from a beautiful river and close proximity to quaint downtown Woodstock or nearby Killington. Felt safe and homey. Great communication from property owner. Would recommend! "

CA $264 total

includes taxes & fees

Aug 21 - Aug 22

"Unit 109, single bedroom queen, was roomy, clean and decorated like a mountain cabin. The porch looked out over a beautiful little stream. Very convenient to Killington, centrally located. Very nice pool. The only inconvenience was the bathroom, which was accessed through the bedroom only, so anyone using the sofa bed in the living room needed to pass through the bedroom to use the bathroom."

CA $270 total

includes taxes & fees

Aug 25 - Aug 26

"We really enjoyed our stay at this home. It had everything we needed and was very comfortable. The countryside around this part of Vermont is beautiful. We found lots of great museums and restaurants. "

CA $1,382 total

includes taxes & fees

Aug 21 - Aug 22

"After a long month of work I needed a weekend in VT to calm the nerves. This was a beautiful spot to be in, glad I was here!"

CA $216 total

includes taxes & fees

Sep 2 - Sep 3

"Great location. Beautiful house. All the amenties. We came up for a ski trip and it was perfect. "

CA $590 total

includes taxes & fees

Sep 3 - Sep 4

"Great location to Mt Snow and its surroundings. Easy, pleasant and accommodating communications with the host. Comfortable accommodations. "

CA $606 total

includes taxes & fees

Aug 22 - Aug 23

"Great condo in great location. Easy walk to restaurants and lifts."

CA $345 total

includes taxes & fees

Aug 24 - Aug 25

"Our room was easy to find and very clean. And the late check-in was very helpful."

CA $218 total

includes taxes & fees

Aug 24 - Aug 25

"What an amazing place! Very serene, clean and big enough for my family of 5. The hosts thought of everything to make our stay comfortable and memorable. Tough to beat the location! We will absolutely return!"

CA $582 total

includes taxes & fees

Sep 8 - Sep 9

"The check in process was so easy, our room was clean and had everything we needed. We would definitely stay here again"

CA $235 total

includes taxes & fees

Sep 7 - Sep 8

"The property was beautiful--great views, super peaceful, and fabulous hosts. "

CA $398 total

includes taxes & fees

Sep 6 - Sep 7

"The place was nice. It was clean, lots of supplies were provided, and it was in a great location. The host contacted me the day before, letting me know that the wifi was out, and the technician was unavailable until the next week. I was appreciative of the heads up. Unfortunately, the TV was unusable without wifi, no option to watch local channels. Cellular (Verizon) data was non-existent throughout the majority of daytime hours. Despite this smallish issue, I would stay here again! "

CA $279 total

includes taxes & fees

Sep 16 - Sep 17

"Great location with plenty of space for the whole family. Highly recommend!"

CA $741 total

includes taxes & fees

Aug 25 - Aug 26

"This was just a few minutes drive from the city of Keene and was a perfect family rental. It had everything we needed. "

CA $763 total

includes taxes & fees

Aug 21 - Aug 22

"We stayed here for one night to ski at Mount Snow and it was amazing! Very comfortable, cozy, well kept, clean with well stocked kitchen. It was perfect for our purpose and would definitely come back!! "

CA $490 total

includes taxes & fees

Aug 23 - Aug 24