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Browse Select Chester Holiday Homes

Tranquil farmhouse in Manchester - perfect for ski or summer fun!

The price is £524
includes taxes & fees
26 Aug - 27 Aug
Tranquil farmhouse in Manchester - perfect for ski or summer fun!

Whimsical Room & Private Bathroom in Historic Inn

8.8 out of 10, Excellent, (9)
"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!"
The price is £118
includes taxes & fees
1 Sept - 2 Sept
Whimsical Room & Private Bathroom in Historic Inn

Charming Chester Farmhouse – peaceful and close to everything!

9.6 out of 10, Exceptional, (12)
"Great location. Beautiful house. All the amenties. We came up for a ski trip and it was perfect. "
The price is £321
includes taxes & fees
8 Sept - 9 Sept
Charming Chester Farmhouse – peaceful and close to everything!

WhiSki Cabin - 12 Acres With a Mountain View!

10.0 out of 10, Exceptional, (3)
"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. "
The price is £741
includes taxes & fees
1 Sept - 2 Sept
WhiSki Cabin - 12 Acres With a Mountain View!

Family Friendly Hilltop House In Putney Vermont

9.4 out of 10, Exceptional, (56)
"The property was beautiful--great views, super peaceful, and fabulous hosts. "
The price is £217
includes taxes & fees
6 Sept - 7 Sept
Family Friendly Hilltop House In Putney Vermont

Cozy Home Near Downtown, Shops, and Restaurants.

2.0 star property
10.0 out of 10, Exceptional, (7)
"This was just a few minutes drive from the city of Keene and was a perfect family rental. It had everything we needed. "
The price is £416
includes taxes & fees
21 Aug - 22 Aug
Cozy Home Near Downtown, Shops, and Restaurants.

110 Deluxe Studio Queen on the 1st floor w/ outdoor heated pool

8.0 out of 10, Very good, (5)
"The view of the river behind the room was great"
The price is £120
includes taxes & fees
21 Aug - 22 Aug
110 Deluxe Studio Queen on the 1st floor w/ outdoor heated pool

Queen Studio on the 2nd floor with outdoor heated pool 207

8.0 out of 10, Very good, (5)
"Overall a good option for a visit to Killington if you don’t need to be on the access road. The outdoor heated pool was a really nice way to relax after a day of skiing. If you don’t want to drive, there is a pretty good restaurant across the street. The only slight concern is if more units than unit 207 are listed on VRBO (the unit we stayed in). I’m glad we had an upstairs unit because the floor was very squeaky. I was wondering if it was annoying the unit below us. With that minor detail...
The price is £129
includes taxes & fees
14 Sept - 15 Sept
Queen Studio on the 2nd floor with outdoor heated pool 207

Cozy 3br condo @West Dover Vt. Heated pool, tennis, pickleball and pool table.

10.0 out of 10, Exceptional, (4)
"Great location to Mt Snow and its surroundings. Easy, pleasant and accommodating communications with the host. Comfortable accommodations. "
The price is £331
includes taxes & fees
22 Aug - 23 Aug
Cozy 3br condo @West Dover Vt. Heated pool, tennis, pickleball and pool table.

Lake Front Family Friendly Escape

10.0 out of 10, Exceptional, (3)
"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!"
The price is £314
includes taxes & fees
8 Sept - 9 Sept
Lake Front Family Friendly Escape

Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts

7.8 out of 10, Good, (50)
"Great condo in great location. Easy walk to restaurants and lifts."
The price is £188
includes taxes & fees
24 Aug - 25 Aug
Stratton Mountain Condo with Shared Pool, Hot Tubs, and Sauna - Walk to Lifts

Brook Bound Inn - Main Lodge - Deluxe King w/ Pullout Couch - Room 203

10.0 out of 10, Exceptional, (1)
"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!! "
The price is £269
includes taxes & fees
21 Aug - 22 Aug
Brook Bound Inn - Main Lodge - Deluxe King w/ Pullout Couch - Room 203

Two Double bed Standard Hotel room 219

7.6 out of 10, Good, (4)
"Very clean and easy access."
The price is £119
includes taxes & fees
25 Aug - 26 Aug
Two Double bed Standard Hotel room 219

Mtn View & Hot Tub-Peaceful Property w/ stream-mins to Hiking, Biking, Swimming

9.0 out of 10, Wonderful, (2)
"Our family had the best time staying here. The home was spacious and gave our two young children plenty of room to roam and explore. It was also close enough to the main road where everything was accessible but also isolated enough where you feel like you're getting away. Erin was great about answering any questions and making sure our stay was comfortable. We'd definitely return here!"
The price is £326
includes taxes & fees
1 Sept - 2 Sept
Mtn View & Hot Tub-Peaceful Property w/ stream-mins to Hiking, Biking, Swimming

Sleep Woodstock - 2 Double Beds - Dog Friendly

10.0 out of 10, Exceptional, (1)
"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! "
The price is £144
includes taxes & fees
27 Aug - 28 Aug
Sleep Woodstock - 2 Double Beds - Dog Friendly

MtSnow* HotTub* Pool * AirHockey*PingPong * Darts

The price is £479
includes taxes & fees
21 Aug - 22 Aug
MtSnow* HotTub* Pool * AirHockey*PingPong * Darts

116 Two Double bed Standard Hotel room

8.6 out of 10, Excellent, (10)
"The place is good. It was our first time here and enjoyed our stay. The brook overlooking our window made the day"
The price is £119
includes taxes & fees
24 Aug - 25 Aug
116 Two Double bed Standard Hotel room

Two Queen Bed Standard Hotel room with outdoor heated pool 201

8.6 out of 10, Excellent, (12)
"Our room was easy to find and very clean. And the late check-in was very helpful."
The price is £119
includes taxes & fees
24 Aug - 25 Aug
Two Queen Bed Standard Hotel room with outdoor heated pool 201

Okemo's Back Room - in the heart of the village on the shuttle route!

9.6 out of 10, Exceptional, (14)
"Perfect location. Charming place to stay. Very clean. Great view of the creek."
The price is £274
includes taxes & fees
21 Aug - 22 Aug
Okemo's Back Room - in the heart of the village on the shuttle route!

104 Two Queen Bed Standard Hotel Room outdoor heated pool

8.6 out of 10, Excellent, (27)
"Excellent customer service and beautiful, well-maintained property."
The price is £119
includes taxes & fees
25 Aug - 26 Aug
104 Two Queen Bed Standard Hotel Room outdoor heated pool
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Chester Hotel Reviews