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Private, Dog-Friendly Estate with Free WiFi, Fireplaces, Washer/Dryer, & Pond

9.4 out of 10, Exceptional, (26)
"Beautiful location and so many cozy touches throughout home!"
Private, Dog-Friendly Estate with Free WiFi, Fireplaces, Washer/Dryer, & Pond

Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable

8.2 out of 10, Very good, (39)
"This place was great for my family and I. It is very close to Okemo and town "
Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable

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 HK$1,641
HK$3,332 total
includes taxes & fees
11 Aug - 12 Aug
Charming Chester Farmhouse – peaceful and close to everything!

Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym

10.0 out of 10, Exceptional, (4)
"Great location, large space for family, good amenities, love the fireplace and coffee set up."
The price is HK$2,296
HK$5,930 total
includes taxes & fees
13 Aug - 14 Aug
Relax & Recover Mountain Retreat - Hot Tub + Sauna + Home Gym

Alpine 6-BR Estate On Okemo Mountain

10.0 out of 10, Exceptional, (2)
"Nice place"
Alpine 6-BR Estate On Okemo Mountain

Premier Woodstock Village Riverfront Home

Premier Woodstock Village Riverfront Home

Timeless Red Sox Retreat w/ Scenic Mountain Views!

10.0 out of 10, Exceptional, (23)
"Beautiful property "
Timeless Red Sox Retreat w/ Scenic Mountain Views!

Lake Rescue Vacation Home- Pets Welcome-Okemo and Killington close!!!

10.0 out of 10, Exceptional, (46)
"Our family had a great stay in Ludlow for a four day ski vacation. Tom and Patti were great hosts and their home is convenient to both Okemo and Killington. The hosts communicated well with us and their place was perfect for our needs (family of 4), clean, and convenient to downtown Ludlow and restaurants. "
Lake Rescue Vacation Home- Pets Welcome-Okemo and Killington close!!!

NEW - Beautiful mountain home steps to Okemo, Great for Wedding stays

10.0 out of 10, Exceptional, (36)
"Our annual trip was great! The house was fantastic and the owners were very friendly and responsive. Would definitely recommend this awesome house!"
NEW - Beautiful mountain home steps to Okemo, Great for Wedding stays

Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location

9.8 out of 10, Exceptional, (173)
"Gorgeous log home , spacious, cozy , fun and comfortable ."
Fabulous Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, BEST Location

Quaint lakefront home with a fire pit and beautiful views

9.4 out of 10, Exceptional, (96)
"We had a great time staying at this cabin. It’s really well located and was perfect for our stay."
Quaint lakefront home with a fire pit and beautiful views

The Mountain Escape!

9.8 out of 10, Exceptional, (17)
"Easy booking, clean home, great location and the owner very easy to get in touch with."
The price is HK$958
HK$4,471 total
includes taxes & fees
11 Aug - 12 Aug
The Mountain Escape!

Cool Barn renovation with views. 5 mins to hikes, restaurants, fishing and more!

10.0 out of 10, Exceptional, (63)
"We had a "
Cool Barn renovation with views. 5 mins to hikes, restaurants, fishing and more!

Beautiful Custom Built Timber Frame Home, Sleeps 11

10.0 out of 10, Exceptional, (105)
"Home was big, clean, and close to mt snow. We had a great stay. Thanks!"
Beautiful Custom Built Timber Frame Home, Sleeps 11

Charming 1-bedroom hotel in peaceful Newfane with AC, WiFi

10.0 out of 10, Exceptional, (1)
"This was the definition of a New England inn!! Super cute and the staff were fantastic! They were so helpful! I would definitely stay here again!! "
The price is HK$1,531
HK$2,013 total
includes taxes & fees
11 Aug - 12 Aug
Charming 1-bedroom hotel in peaceful Newfane with AC, WiFi

PRIVATE & AFFORDABLE charming custom ranch in S. Woodstock. WIFI and AC.

9.8 out of 10, Exceptional, (218)
"Our stay was amazing! The house offered everything we needed, was spacious and clean. Working with the owners was also easy. Would definitely recommend and stay again!"
PRIVATE & AFFORDABLE charming custom ranch in S. Woodstock. WIFI and AC.

Woodstock Carriage House-280 acres-Views-Gardens-Skiing-Farm-2.5 miles from town

10.0 out of 10, Exceptional, (53)
"Cozy accommodations, great location, beautiful property, wonderful hosts."
Woodstock Carriage House-280 acres-Views-Gardens-Skiing-Farm-2.5 miles from town

Cozy cottage tucked away in the woods

10.0 out of 10, Exceptional, (43)
"Nice and comfy - loved the decor and the property."
Cozy cottage tucked away in the woods

Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi

9.8 out of 10, Exceptional, (25)
"Beautiful place."
Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi

Historic Charm, Located On the River - Rustic Chic

10.0 out of 10, Exceptional, (1)
"Amazing location and great house!! "
Historic Charm, Located On the River - Rustic Chic
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