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Check prices for these dates

Next weekend
8 Aug - 10 Aug
In two weeks
15 Aug - 17 Aug
In one month
29 Aug - 31 Aug
In two months
26 Sep - 28 Sep

Condo Rentals in Chester

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

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

9.6 out of 10, Exceptional, (39)
"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
Bright & cheery condo with seasonal pool access
Property grounds

Bright & cheery condo with seasonal pool access

8.2 out of 10, Very Good, (39)
"Perfect for adults and kids looking to ski. Easy access. Clean and easy rental"
Bright & cheery condo with seasonal pool access
Coveted Ski-In/Ski-Out Winterplace Condo with Hot Tubs, Indoor Pool & Fireplace
Exterior

Coveted Ski-In/Ski-Out Winterplace Condo with Hot Tubs, Indoor Pool & Fireplace

9.2 out of 10, Wonderful, (17)
"We loved our stay at the Winterplace condo. It was clean and so easy to find, park and best of all ski out of!"
Coveted Ski-In/Ski-Out Winterplace Condo with Hot Tubs, Indoor Pool & 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, (51)
"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 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
Dog-friendly & riverfront condo one mile from Okemo with wood fireplace
Terrace/patio

Dog-friendly & riverfront condo one mile from Okemo with wood fireplace

8.8 out of 10, Excellent, (19)
"Great Location. Inside of place was great. "
Dog-friendly & riverfront condo one mile from Okemo with wood fireplace
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, (175)
"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
Ski-in/out mountainside condo with pool, hot tub, game room & washer/dryer
Fridge, microwave, oven, stovetop

Ski-in/out mountainside condo with pool, hot tub, game room & washer/dryer

9.6 out of 10, Exceptional, (14)
"This was a great place to stay. Clean, spacious, and gorgeous. I love the fully stocked kitchen, the games for the family, and relaxing spa like bathrooms."
Ski-in/out mountainside condo with pool, hot tub, game room & washer/dryer
Ski-in/out condo with fireplace, hot tubs. pool, tennis & washer/dryer
Property grounds

Ski-in/out condo with fireplace, hot tubs. pool, tennis & washer/dryer

9.4 out of 10, Exceptional, (25)
"Great ski in ski out location. Lift is right next to condo"
Ski-in/out condo with fireplace, hot tubs. pool, tennis & washer/dryer
★No Cleaning Fee★10% OFF★Walk To Mountain★Amenities+
Fridge, microwave, oven, stovetop

★No Cleaning Fee★10% OFF★Walk To Mountain★Amenities+

10.0 out of 10, Exceptional, (50)
"From beginning to end, a great experience:the owners are very responsive throughout the process, check-in and parking was a breeze, condo is great, location is perfect -- right across the street from the village -- we had a wonderful time -- thank you Brandon!!"
★No Cleaning Fee★10% OFF★Walk To Mountain★Amenities+
Summer retreat! Mountain View, Walk to Village/Tennis/Fitness/Dance camps; HITS
Fridge, microwave, oven, stovetop

Summer retreat! Mountain View, Walk to Village/Tennis/Fitness/Dance camps; HITS

10.0 out of 10, Exceptional, (41)
"We came to spend the day at Bromley. We climbed stratton as well in the rain. We had a great time"
Summer retreat! Mountain View, Walk to Village/Tennis/Fitness/Dance camps; HITS
Mountainside Luxury 2-Level Condo at Okemo. Ski-In/Out.
Property grounds

Mountainside Luxury 2-Level Condo at Okemo. Ski-In/Out.

10.0 out of 10, Exceptional, (34)
"We loved staying here. Such a wonderful experience. "
Mountainside Luxury 2-Level Condo at Okemo. Ski-In/Out.
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: 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
Ski-in/ski-out condo with resort amenities and mountain views
Exterior

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
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 SAR 326
SAR 1,129 total
includes taxes & fees
14 Aug - 15 Aug
Lovely ski-in/out condo steps from ski lift with trails and amazing views
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, (168)
"Wonderful host / fantastic location "
Seasons On Mount Snow - Ski-in/Ski-out
Summer Adventure Park Trail Side Condo
Outdoor pool, a heated pool

Summer Adventure Park Trail Side Condo

9.8 out of 10, Exceptional, (36)
"Very happy with our stay. If you’re looking for a comfortable, clean condo in a fantastic location that is reasonably priced this is the spot!"
Summer Adventure Park Trail Side Condo
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 SAR 473
SAR 1,026 total
includes taxes & fees
4 Aug - 5 Aug
2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
Beautiful Spacious Condo at Killington Resort
Fridge, microwave, oven, stovetop

Beautiful Spacious Condo at Killington Resort

9.8 out of 10, Exceptional, (38)
"Beautiful, very spacious condo."
Beautiful Spacious Condo at Killington Resort
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

Woodstock Inn & Resort

Woodstock Inn & Resort

10/10 Excellent
"Bed was more comfortable than home. Dinner at Richardson’s Grill was fantastic. Breakfast buffet was mediocre. Room was very nice but bathroom needed updating."
Susan 2-night trip
Posted 2 days ago
Woodstock Inn & Resort

Frequently asked questions

How much do condos in Chester cost?
Condos in Chester range from SAR 326 to SAR 473 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 504 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.