Search Condos Rentals in Chester from CA $113

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Check prices for these dates

Next weekend
Jul 11 - Jul 13
In two weeks
Jul 18 - Jul 20
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Aug 1 - Aug 3
In two months
Aug 29 - Aug 31

Browse Select Chester Condo Rentals

Ski In/Out Sunrise West Glade 3 BR 3 BA Trailside, Sauna, Pool, Hot Tub
3 bedrooms, iron/ironing board, free WiFi, bed sheets

Ski In/Out Sunrise West Glade 3 BR 3 BA Trailside, Sauna, Pool, Hot Tub

3.0 star property
9.6 out of 10, Exceptional, (11)
"Excellent location"
Ski In/Out Sunrise West Glade 3 BR 3 BA Trailside, Sauna, Pool, Hot Tub
Renovated Ski-In/Ski-Out Peru Condo at Bromley Mtn
Aerial view

Renovated Ski-In/Ski-Out Peru Condo at Bromley Mtn

9.6 out of 10, Exceptional, (36)
"Great stay, super easy access to the slopes. Place was great with helpful and communicable hosts. Will stay again! "
Renovated Ski-In/Ski-Out Peru Condo at Bromley Mtn
SUNRISE 3BR - 2 Story Remodeled Condo - SKI ON & OFF. Pool + Trailside
Indoor pool, outdoor pool

SUNRISE 3BR - 2 Story Remodeled Condo - SKI ON & OFF. Pool + Trailside

10.0 out of 10, Exceptional, (172)
"Great location for ski on/off, updated kitchen and bathrooms, quiet, spacious and comfortable. Plan on coming back."
SUNRISE 3BR - 2 Story Remodeled Condo - SKI ON & OFF. Pool + Trailside
Cozy Townhome with Shared Pool & Tennis, W/D & Wood-Burning Fireplace
TV, fireplace

Cozy Townhome with Shared Pool & Tennis, W/D & Wood-Burning Fireplace

9.2 out of 10, Wonderful, (5)
"Absolutely loved my stay here. It's as clean, and nice and the whole process was easy. I would definitely come back."
Cozy Townhome with Shared Pool & Tennis, W/D & Wood-Burning Fireplace
Ski-in/out condo with pool, 2 hot tubs, sauna - short walk to Solitude clubhouse
TV, fireplace, video games, DVD player

Ski-in/out condo with pool, 2 hot tubs, sauna - short walk to Solitude clubhouse

9.4 out of 10, Exceptional, (29)
"Nice location steps off of Moonshadow trail. "
Ski-in/out condo with pool, 2 hot tubs, sauna - short walk to Solitude clubhouse
Lovely ski-in/out condo steps from ski lift with trails and amazing views
TV, fireplace

Lovely ski-in/out condo steps from ski lift with trails and amazing views

8.6 out of 10, Excellent, (24)
"We loved staying at the townhome. It was a welcome place to stay while we traveled around, enjoying fall. It was very comfortable and the village amenities were great."
The price is CA $113
CA $402 total
includes taxes & fees
Jul 7 - Jul 8
Lovely ski-in/out condo steps from ski lift with trails and amazing views
Mountain Home w/Balcony, Pool Views, Shared Pool, Hot Tub, Free WiFi, Fireplace
Exterior

Mountain Home w/Balcony, Pool Views, Shared Pool, Hot Tub, Free WiFi, Fireplace

9.0 out of 10, Wonderful, (21)
"The condo is very close to everything and the perfect amount of room for a family of 5. Great outdoor pools and 2 hot tubs too!"
Mountain Home w/Balcony, Pool Views, Shared Pool, Hot Tub, Free WiFi, Fireplace
Inviting condo with a fireplace, hot tubs, pool, tennis & washer/dryer
Property grounds

Inviting condo with a fireplace, hot tubs, pool, tennis & washer/dryer

9.2 out of 10, Wonderful, (50)
"The stay itself was wonderful. The apartment is fantastic for its location, cleanliness, and amenities. Unfortunately, being on the second floor with people above you there can be a lot of noise. Pool was wonderful. Walk to skiing is fantastic. Would happily come back"
Inviting condo with a fireplace, hot tubs, pool, tennis & washer/dryer
Ski-in/out condo with water & mountain views, private sauna & fireplace
TV, fireplace

Ski-in/out condo with water & mountain views, private sauna & fireplace

9.8 out of 10, Exceptional, (45)
"This condo was super clean, well appointed, comfortable for our family, and the absolute perfect location for ski in/ski out convenience. Highly recommend!"
Ski-in/out condo with water & mountain views, private sauna & fireplace
Charming 1-bedroom condo in delightful Dover
Fridge, microwave, oven, stovetop

Charming 1-bedroom condo in delightful Dover

10.0 out of 10, Exceptional, (1)
"Amenities are fine. All needs extremely fully available. Kitchen well stocked. Bed was comfortable. "
The price is CA $145
CA $276 total
includes taxes & fees
Jul 7 - Jul 8
Charming 1-bedroom condo in delightful Dover
Slopeside condo with nearby skiing, balcony, fireplace, & washer/dryer
Fridge, microwave, oven, stovetop

Slopeside condo with nearby skiing, balcony, fireplace, & washer/dryer

8.6 out of 10, Excellent, (17)
"Great location for ski lovers"
Slopeside condo with nearby skiing, balcony, fireplace, & washer/dryer
Ski-In/ski-out condo with views, pool, hot tubs, gym & tennis access
Fridge, microwave, oven, stovetop

Ski-In/ski-out condo with views, pool, hot tubs, gym & tennis access

8.4 out of 10, Very good, (56)
"This property was a great place to stay and enjoy the quite Vermont wilderness. We took advantage of the clubhouse pool and hot tub as well as scenic woodland walks through the trails right outside the front door."
Ski-In/ski-out condo with views, pool, hot tubs, gym & tennis access
Seasons On Mount Snow - Ski-in/Ski-out
Indoor pool, a heated pool

Seasons On Mount Snow - Ski-in/Ski-out

9.8 out of 10, Exceptional, (166)
"Wonderful host / fantastic location "
Seasons On Mount Snow - Ski-in/Ski-out
Experience the ultimate Vermont getaway at our cozy 1BR/1BA ski-in/ski-out condo in Killington
Exterior

Experience the ultimate Vermont getaway at our cozy 1BR/1BA ski-in/ski-out condo in Killington

The price is CA $274
CA $625 total
includes taxes & fees
Jul 7 - Jul 8
Experience the ultimate Vermont getaway at our cozy 1BR/1BA ski-in/ski-out condo in Killington
Seasons Lodge | Trailside Condo w/ Fireplace!
Pool

Seasons Lodge | Trailside Condo w/ Fireplace!

10.0 out of 10, Exceptional, (7)
"Very well maintained space with everything a family needs to have a good time skiing. "
Seasons Lodge | Trailside Condo w/ Fireplace!
Perfect Okemo Ski Location! Winterplace 3 Bedroom Condo- Short Walk to Slopes!
Exterior

Perfect Okemo Ski Location! Winterplace 3 Bedroom Condo- Short Walk to Slopes!

10.0 out of 10, Exceptional, (57)
"We had a great time at the wonderful Winterplace condo. The host was very responsive . "
Perfect Okemo Ski Location! Winterplace 3 Bedroom Condo- Short Walk to Slopes!
Ski-in/ski-out condo with resort amenities and mountain views
Indoor pool, a heated pool

Ski-in/ski-out condo with resort amenities and mountain views

8.0 out of 10, Very good, (7)
"Plenty of space for our group!"
Ski-in/ski-out condo with resort amenities and mountain views
Ski-In/Ski-out Condo: Most accessible location on Okemo Mountain
TV, fireplace

Ski-In/Ski-out Condo: Most accessible location on Okemo Mountain

9.8 out of 10, Exceptional, (8)
"Family had a great trip thanks"
Ski-In/Ski-out Condo: Most accessible location on Okemo Mountain
Comfortable condo with fireplace, pool, and sauna access - near slopes
Fridge, microwave, oven, stovetop

Comfortable condo with fireplace, pool, and sauna access - near slopes

8.4 out of 10, Very good, (14)
"Perfect location. On the MOOver line. Plenty of space for my family of four. "
Comfortable condo with fireplace, pool, and sauna access - near slopes
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, (96)
"Convenient 2 BR space with comfy beds right in the heart of Ludlow. Would definitely stay there again."
The price is CA $145
CA $338 total
includes taxes & fees
Jul 7 - Jul 8
2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
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 CA $113 to CA $274 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.