Search Vacation Homes in Chester

Check prices for these dates

Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24
In one month
Sep 5 - Sep 7
In two months
Oct 3 - Oct 5

Vacation Homes in Chester

Private, Dog-Friendly Estate with Free WiFi, Fireplaces, Washer/Dryer, & Pond
TV, fireplace, video games

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
Quaint lakefront home with a fire pit and beautiful views
Property grounds

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
Classic ski home with hot tub, washer/dryer, mountain views, fireplace, & cable
Fridge, microwave, oven, stovetop

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
Breaktime - Quiet and Private on dead end street
Property grounds

Breaktime - Quiet and Private on dead end street

10.0 out of 10, Exceptional, (30)
"I like the location close to mountain walking trails and fine dining options. "
Breaktime - Quiet and Private on dead end street
Pet-Friendly Claremont Vacation Rental!
Terrace/patio

Pet-Friendly Claremont Vacation Rental!

8.8 out of 10, Excellent, (5)
"Only will stay here! "
Pet-Friendly Claremont Vacation Rental!
Ski-in/out home with a hot tub, fireplace, cable & golf nearby
Outdoor dining

Ski-in/out home with a hot tub, fireplace, cable & golf nearby

9.4 out of 10, Exceptional, (23)
"Nice and roomy. Plenty of room throughout the entire house. Kitchen area LARGE. back deck was nice with the hot tub. Ski run steps from the house. Really nice place."
Ski-in/out home with a hot tub, fireplace, cable & golf nearby
PRIVATE & AFFORDABLE charming custom ranch in S. Woodstock. WIFI and AC.
Exterior

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.
Tasteful Country Home on 5 Acres ~ 3 Mi to Lake!
View from property

Tasteful Country Home on 5 Acres ~ 3 Mi to Lake!

10.0 out of 10, Exceptional, (6)
"In town for funeral, the place was great. Very roomy and comfy."
Tasteful Country Home on 5 Acres ~ 3 Mi to Lake!
Heated Saltwater Pool: Riverfront Home in Ludlow
A heated pool

Heated Saltwater Pool: Riverfront Home in Ludlow

10.0 out of 10, Exceptional, (12)
"We had a wonderful stay. The house was very clean and well maintained and very well stocked. The pool and surrounding area were beautiful. We enjoyed day hikes at buttermilk falls and echo lake, which are so close by. We highly recommend this place to anyone looking to spend a few relaxing days in Vermont."
Heated Saltwater Pool: Riverfront Home in Ludlow
Timeless Red Sox Retreat w/ Scenic Mountain Views!
Fridge, microwave, stovetop, dishwasher

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

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
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
Outdoor spa tub

Your Vermont Mountain Haven Pet Friendly home with Hot tub!

9.8 out of 10, Exceptional, (21)
"This place was very enjoyable, it was just 3 of us so there was more than enough room. It is a very comfortable home and we enjoyed the easy trip into Manchester for some meals and a wonderful day of hiking some great nearby trails."
$574 nightly
The price is $644
Aug 17 - Aug 18
Total includes taxes and fees
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
The Mountain Escape!
Outdoor spa tub

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."
$504 nightly
The price is $570
Aug 7 - Aug 8
Total includes taxes and fees
The Mountain Escape!
Woodstock Carriage House-280 acres-Views-Gardens-Skiing-Farm-2.5 miles from town
Fridge, microwave, oven, stovetop

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
Beautiful Custom Built Timber Frame Home, Sleeps 11
Smart TV, fireplace, DVD player, table tennis

Beautiful Custom Built Timber Frame Home, Sleeps 11

10.0 out of 10, Exceptional, (103)
"Home was big, clean, and close to mt snow. We had a great stay. Thanks!"
Beautiful Custom Built Timber Frame Home, Sleeps 11
Historic Renovated Barn at Boorn Brook Farm - Manchester Vermont
Dining

Historic Renovated Barn at Boorn Brook Farm - Manchester Vermont

10.0 out of 10, Exceptional, (201)
"This location is awesome. Close to town and skiing but we felt like we were secluded in the forest when sitting in the hot tub. We had a great time!"
Historic Renovated Barn at Boorn Brook Farm - Manchester Vermont
Private, new home near Skyeship gondola with four fireplaces, washer/dryer, WiFi
Property grounds

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
Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge
Property grounds

Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge

9.8 out of 10, Exceptional, (212)
"Only a 4 minute drive from the slopes!"
Lake front house about 1 mile from Okemo's Jackson Gore Base Lodge
Family Home w/ Great Yard, Fireplace, Kayaks, AC & WiFi - Near Skiing/Lakes
Interior

Family Home w/ Great Yard, Fireplace, Kayaks, AC & WiFi - Near Skiing/Lakes

10.0 out of 10, Exceptional, (24)
"Great location close to the slopes. Clean and comfortable. Loved the fireplace. "
Family Home w/ Great Yard, Fireplace, Kayaks, AC & WiFi - Near Skiing/Lakes
Pet-Friendly! Hot Tub | Marsh Family Road Retreat
Interior

Pet-Friendly! Hot Tub | Marsh Family Road Retreat

9.2 out of 10, Wonderful, (9)
"Wassil weekend was everything it promised to be. Definitely worth tbe trip."
Pet-Friendly! Hot Tub | Marsh Family Road Retreat
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chester Hotel Reviews

Hampton Inn and Suites Manchester

Hampton Inn and Suites Manchester

10/10 Excellent
"We really enjoyed our stay at this property. It's nicely kept.. and EV charging is included in stay. Great breakfast, too. "
Deberah L 2-night trip
Posted 1 day ago
Hampton Inn and Suites Manchester