14 Results
Cancel Clear Filters Apply Filters

Price Per Week

$ $

Sleeps

Bedrooms

Bathrooms

Booking Options

Property Type

Cabins
Cottages
Farmhouses
Homes
Apartments
Barns
Boats
Bungalows
Castles
Chalets
Condos
Estates
Hotels
Lodges
Studios
Townhomes
Villas
Yachts

Booking Options

Location Type

Even More Filters

Features

Managed By

14 Results
Cancel Clear Filters Apply Filters
Use filters to narrow your search results!

Chester Vacation Rentals(14)

14 Results
$280 - $400
per night
2 - 3 night min stay
  • 5 BR,
  • Sleeps 12
2 - 3 night min stay
(5)
$157 - $350
per night
2 - 7 night min stay
  • 3 BR,
  • 2 BA,
  • Sleeps 12
2 - 7 night min stay
(11)
  • 3 BR,
  • 2 BA,
  • Sleeps 6
2 night min stay
1 Review
  • 5 BR,
  • 3 BA,
  • Sleeps 10
$100 - $140
per night
2 night min stay
  • 2 BR,
  • 1 BA,
  • Sleeps 4
2 night min stay
(12)
  • 2 BR,
  • 1 BA,
  • Sleeps 6
2 night min stay
(9)
  • 7 BR,
  • 3 BA,
  • 1 HF BA,
  • Sleeps 16
3 night min stay
  • Studio,
  • 1 BA,
  • Sleeps 5
2 Reviews
$125 - $150
per night
2 - 3 night min stay
  • 5 BR,
  • 1 BA,
  • 1 HF BA,
  • Sleeps 11
2 - 3 night min stay
2 Reviews
  • 2 BR,
  • 1 BA,
  • Sleeps 10
2 night min stay
1 Review
  • 4 BR,
  • 2 BA,
  • Sleeps 8
2 - 4 night min stay
1 Review
  • 3 BR,
  • 1 BA,
  • Sleeps 6
2 - 5 night min stay
  • 2 BR,
  • 1 BA,
  • Sleeps 5
2 night min stay
(20)
$200 - $300
per night
3 - 7 night min stay
  • 3 BR,
  • 2 BA,
  • Sleeps 8
3 - 7 night min stay
(9)
 View map Map
Advertisement
 

Recent Chester Reviews

A Wonderful Get Away!

5 of 5
This charming Farmhouse is the perfect get away for extended family or a group of friends! My family fit comfortably in the house, relaxed by the fire, and had some great meals with plenty of places to sit. It was a quick drive to Okemo Mt (20 minutes) for those of us who chose to ski, and plenty to do for those who do not ski. It is a quick ride into downtown Ludlow with places to eat, or we could stay on the farm and enjoy the beautiful Vermont surroundings. I highly recommend taking a wonderful horse drawn sleigh ride around the farm and through the woods on their property, as well as visit the many sheep and horses they have on the farm. The owners of the farm are extremely friendly and accommodating. The pictures of this farm house do not do it justice, we all found it to be larger and even more charming in person than the pictures portray!
  • Submitted: Jan 20, 2015
  • Stayed: Jan 2015

Really would have loved to stay forever!

5 of 5
You couldn't ask for more from this great cabin in the woods. All the makings of a relaxing retreat with activities close by for those that want. Spent most of our time relaxing either by the river listening to the rushing water, having coffee and reading on the back porch, or curled up in the cozy living room using all the modern amenities! Had a great time exploring the area as well. Yummy restaurants right in Chester, Bromley Mountain in summer was a blast and Manchester pretty much has anything you may be looking to shop for.
  • Submitted: Oct 10, 2014
  • Stayed: Jul 2014

Great cabin in an awesome town!

5 of 5
The owner was extremely accommodating and thoughtful. Our first time here was back in January during a big winter storm. The owner was kind enough to let us go up a day early, free of charge, so that we did not have to drive up during the storm. We were blown away by his kindness. The cabin is cozy and charming with everything you need. There is a nice wood stove with plenty of firewood, it was -15 degrees outside but we were nice and toasty inside. There is a huge selection of DVDs that we took advantage of and got to watch some great movies while we were snowed in. The town of Chester itself is a great town to stay in. You don't get much of the ski crowd, but Ludlow, VT and other ski areas are only a few minutes away. There are some great antique stores nearby including our personal favorite, Wyndham Antique Center in Bellow Falls. I highly recommend this cabin to anyone looking for a place to unwind. P.S.- Do yourself a favor and get some Blue Wings at Stone Hearth Inn & Tavern, you can thank me later.
  • Submitted: Feb 17, 2014
  • Stayed: Jan 2014