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Check prices for these dates

Next weekend
Jul 4 - Jul 6
In two weeks
Jul 11 - Jul 13
In one month
Jul 25 - Jul 27
In two months
Aug 22 - Aug 24

Condo Rentals in Chester

Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort
Exterior

Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort

10.0 out of 10, Exceptional, (18)
"Lovely large property, everything was clean and well maintained! Will happily stay there again!"
$482 nightly
The price is $540
Jun 24 - Jun 25
Total includes taxes and fees
Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort
2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
Microwave, oven, stovetop, dishwasher

2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route

10.0 out of 10, Exceptional, (95)
"We loved Wendy's place. It was clean, updated and had everything we needed. Its in the center of town so convenient to shops and restaurants and close to the mountain. We will be booking again. "
$246 nightly
The price is $266
Jul 7 - Jul 8
Total includes taxes and fees
2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
Condo in the heart of town near skiing - less than a mile to Okemo Mountain
Fridge, microwave, oven, stovetop

Condo in the heart of town near skiing - less than a mile to Okemo Mountain

9.0 out of 10, Wonderful, (13)
"Great location and very comfortable."
$223 nightly
The price is $252
Jul 15 - Jul 16
Total includes taxes and fees
Condo in the heart of town near skiing - less than a mile to Okemo Mountain
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
Property grounds

Ski-in/out mountainside condo close to everything with full kitchen - tranquil

9.0 out of 10, Wonderful, (72)
"Dated but well appointed and comfortable condo. Be prepared for lots of stairs but great location directly slopeside."
$238 nightly
The price is $266
Jun 24 - Jun 25
Total includes taxes and fees
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
TV, DVD player

Ski-In/Out condo with patio, mountain views, washer/dryer, & cable

9.4 out of 10, Exceptional, (24)
"Great location for ski in ski out unit on 1st floor. Steps away from clock tower base and lift. Easy access to post ski fun for drink/dining super close The Loft or The Bull both 2 mins walk from condo. "
$205 nightly
The price is $230
Jun 28 - Jun 29
Total includes taxes and fees
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
Ground Floor ski-in/out condo, full kitchen & high-speed WiFi
Exterior

Ground Floor ski-in/out condo, full kitchen & high-speed WiFi

9.4 out of 10, Exceptional, (20)
"Enjoy our stay !!!!! Awesome in and out right on the slope feet away for deck."
$348 nightly
The price is $390
Jun 24 - Jun 25
Total includes taxes and fees
Ground Floor ski-in/out condo, full kitchen & high-speed WiFi
Okemo | Charming 1BR Condo + Close to Amenities
Exterior

Okemo | Charming 1BR Condo + Close to Amenities

$279 nightly
The price is $305
Jun 25 - Jun 26
Total includes taxes and fees
Okemo | Charming 1BR Condo + Close to Amenities
Okemo | 1BR + Loft Condo + Close to All Amenities
Exterior

Okemo | 1BR + Loft Condo + Close to All Amenities

$317 nightly
The price is $346
Jun 25 - Jun 26
Total includes taxes and fees
Okemo | 1BR + Loft Condo + Close to All Amenities
Okemo | 3BR Condo & Close to Amenities + Slopes!
Exterior

Okemo | 3BR Condo & Close to Amenities + Slopes!

$411 nightly
The price is $450
Jun 25 - Jun 26
Total includes taxes and fees
Okemo | 3BR Condo & Close to Amenities + Slopes!
Okemo | 3BR + Loft Condo & Close to All Amenities
Exterior

Okemo | 3BR + Loft Condo & Close to All Amenities

$591 nightly
The price is $646
Jun 26 - Jun 27
Total includes taxes and fees
Okemo | 3BR + Loft Condo & Close to All Amenities
Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
Fridge, microwave, oven, stovetop

Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails

7.6 out of 10, Good, (53)
"This cozy cabin was perfect for a ski weekend with friends. We really enjoyed gathering by the stone fireplace after a couple long days out on the slopes."
$245 nightly
The price is $275
Jun 24 - Jun 25
Total includes taxes and fees
Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
Cozy 3 bedroom condo 2.5 miles to Mount Snow
Property grounds

Cozy 3 bedroom condo 2.5 miles to Mount Snow

9.2 out of 10, Wonderful, (39)
"This is the third time I’ve stayed here and it’s very convenient and I really love what the host did for upgrades on the property. "
$263 nightly
The price is $297
Jun 30 - Jul 1
Total includes taxes and fees
Cozy 3 bedroom condo 2.5 miles to Mount Snow
Ski-In/Out Condo with Mountain Views, and Washer/Dryer
Dining

Ski-In/Out Condo with Mountain Views, and Washer/Dryer

9.8 out of 10, Exceptional, (16)
"Location location location!"
$357 nightly
The price is $400
Jun 24 - Jun 25
Total includes taxes and fees
Ski-In/Out Condo with Mountain Views, and Washer/Dryer
Hawk Mountain retreat near Okemo with wifi, washer/dryer & deck
Fridge, microwave, oven, stovetop

Hawk Mountain retreat near Okemo with wifi, washer/dryer & deck

9.8 out of 10, Exceptional, (23)
"convenient to okemo"
$558 nightly
The price is $625
Jun 24 - Jun 25
Total includes taxes and fees
Hawk Mountain retreat near Okemo with wifi, washer/dryer & deck
Charming 1-bedroom condo in delightful Dover
Fridge, microwave, oven, stovetop

Charming 1-bedroom condo in delightful Dover

$156 nightly
The price is $176
Jul 1 - Jul 2
Total includes taxes and fees
Charming 1-bedroom condo in delightful Dover
Mount Snow Condo: 4 min Walk to Sundance Lift (High Speed - 6 Seat)
Property grounds

Mount Snow Condo: 4 min Walk to Sundance Lift (High Speed - 6 Seat)

9.4 out of 10, Exceptional, (18)
"Clean, comfortable, convenient! "
$428 nightly
The price is $484
Jun 24 - Jun 25
Total includes taxes and fees
Mount Snow Condo: 4 min Walk to Sundance Lift (High Speed - 6 Seat)
NEW Ski in/out condo with Mt views, hot tub, porch, gym & wifi!
Microwave, oven, stovetop, dishwasher

NEW Ski in/out condo with Mt views, hot tub, porch, gym & wifi!

10.0 out of 10, Exceptional, (1)
"Excellent stay super close to the mtn. "
$323 nightly
The price is $365
Jul 1 - Jul 2
Total includes taxes and fees
NEW Ski in/out condo with Mt views, hot tub, porch, gym & wifi!
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
Property grounds

Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities

8.4 out of 10, Very Good, (27)
"This condo was as advertised. Perfect location to mountain snow, and quick ride into town. Would stay here again. "
$265 nightly
The price is $300
Jun 24 - Jun 25
Total includes taxes and fees
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
2BR Loft With Views | Ski-In Access
Property grounds

2BR Loft With Views | Ski-In Access

$372 nightly
The price is $411
Jul 10 - Jul 11
Total includes taxes and fees
2BR Loft With Views | Ski-In Access
Expansive 2BR | Sleeps 10 | Ski-In
Property grounds

Expansive 2BR | Sleeps 10 | Ski-In

$451 nightly
The price is $498
Jul 10 - Jul 11
Total includes taxes and fees
Expansive 2BR | Sleeps 10 | Ski-In
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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Frequently asked questions

How much do condos in Chester cost?
Condos in Chester range from $176 to $646 per night. This gives you lots of space for your whole family at a price that's easy on your wallet. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.
How many condos are there in Chester?
Choose from 509 condos in Chester. No matter if you're traveling with the little ones or planning a getaway with friends, Expedia will help you find the perfect space for your squad.
Why book your condo in Chester with Expedia?
Getaways should be a piece of cake, so if you're in search of condos at a great price, Expedia has you covered. Keep the budget in check and go for something small and affordable, or book 5-star accommodations and treat your loved ones. Our search filters make it easy to find a stay in Chester that suits your needs.