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Compare 505 Condo Rentals in Chester with updated reviews, rates, and availability.

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

9.8 out of 10, Exceptional, (165)
"Wonderful host / fantastic location "
Seasons On Mount Snow - Ski-in/Ski-out

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

10.0 out of 10, Exceptional, (171)
"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 condo with a fireplace, hot tub, gym, pool, washer/dryer & cable

8.2 out of 10, Very Good, (19)
"Unfortunately there was a hot water heater issue and the management company could not fixit nor provide a replacement property ahead of a busy holiday weekend."
Ski-in/out condo with a fireplace, hot tub, gym, pool, washer/dryer & cable

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

10.0 out of 10, Exceptional, (18)
"Our stay was great. The place is clean, well stocked, and spacious. It felt like we were staying at a friend’s place. "
The price is SAR 1,125
SAR 2,025 total
includes taxes & fees
24 Apr - 25 Apr
Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort

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

9.0 out of 10, Wonderful, (72)
"Perfect location for a quick ski trip. "
The price is SAR 281
SAR 995 total
includes taxes & fees
25 Apr - 26 Apr
Ski-in/out mountainside condo close to everything with full kitchen - tranquil

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

3.0 star property
9.8 out of 10, Exceptional, (7)
"The location of this unit was ideal for people who like to vacation without having to drive. We literally skied to The Sunrise Cafe for dinner the first night. All of our outdoor adventures started right from our door with excellent access to trails. The Community center had a great hot tub and free equipment to use. We would definitely go back. "
Ski In/Out Sunrise West Glade 3 BR 3 BA Trailside, Sauna, Pool, Hot Tub

Mountain-view condo with private balcony, fireplace, & updated interior

7.8 out of 10, Good, (14)
"A short walk to the base of Stratton, my son hiked to the peak and loved the views! It's close to other towns, and a perfectly outfitted condo with plenty of space and amenities. Dishwasher hadn't been emptied (a note for the cleaning service) but otherwise was neat and clean. Thank you!"
Mountain-view condo with private balcony, fireplace, & updated interior

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

8.4 out of 10, Very Good, (14)
"Just stayed for the weekend & had a really great experience! The furniture & hot tub have been updated since the photos on the ad have been taken. Great view of the mountain & all the appliances also looked really new. Definitely bring bedding for the pull out couch if you plan to use it as th"
Comfortable condo with fireplace, pool, and sauna access - near slopes

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

9.4 out of 10, Exceptional, (12)
"The condo was perfect, just what we were looking for. Vacasa is the management firm and they are very difficult to work with. They gave us the wrong door code to begin with so after trying to open the door in the freezing cold with children at night we had to go back to the car and wait on hold to get in touch with vacasa to eventually get the right code. The condo comes with two parking passes but we had a third card as the condo accomodates 10 people. I asked vacasa where a 3rd car could park...
Ski-in/out mountainside condo with pool, hot tub, game room & washer/dryer

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

8.4 out of 10, Very Good, (56)
"Cold first night"
Ski-In/ski-out condo with views, pool, hot tubs, gym & tennis access

Renovated Ski-in/Ski-Out Condo w/ Shared Pools, Hot Tub, Sauna & Great Location

8.6 out of 10, Excellent, (47)
"Access to trail was great. Condo had everything we needed. Bathrooms recently renovated. "
Renovated Ski-in/Ski-Out Condo w/ Shared Pools, Hot Tub, Sauna & Great Location

Condo near ski trail with fireplace, hot tub, pool, tennis & washer/dryer

9.4 out of 10, Exceptional, (36)
"We really enjoyed our stay. The condo was the perfect size for our group. Its location offered a lot of flexibility — everyone could ski as much or as little as they wanted to, being able to ski in/out as they wished. "
Condo near ski trail with fireplace, hot tub, pool, tennis & washer/dryer

Charming 3BR/2BA Condo in Sunrise Village at Killington. Pool. Hot Tub. Sports Center.

9.0 out of 10, Wonderful, (2)
"We had a special ski weekend with friends. "
The price is SAR 928
SAR 2,327 total
includes taxes & fees
24 Apr - 25 Apr
Charming 3BR/2BA Condo in Sunrise Village at Killington. Pool. Hot Tub. Sports Center.

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

8.8 out of 10, Excellent, (23)
"Wonderful location and comfortable. Appliances were a bit dated, but that didn’t impact our stay. The unit was not cleaned from the previous occupants upon our check in and took a few hours to do so. This is not the fault of the owner, but did impact our initial experience. Overall wonderful though. Great location and comfortable with a working fireplace. Would stay here again. "
The price is SAR 266
SAR 1,049 total
includes taxes & fees
24 Apr - 25 Apr
Lovely ski-in/out condo steps from ski lift with trails and amazing views

Stratton Mtn Studio | Renovated | Walk to Lifts

10.0 out of 10, Exceptional, (28)
"Nicely renovated, well equipped condo very conveniently close to the main lodge and all it offers. It is small but for two people it certainly is fine and murphy bed is a clever solution. Well done!"
The price is SAR 523
SAR 1,388 total
includes taxes & fees
24 Apr - 25 Apr
Stratton Mtn Studio | Renovated | Walk to Lifts

Beautifully renovated 2 bedroom condo in Stratton VT - walk to Village/Lifts!

10.0 out of 10, Exceptional, (11)
"The unit was very nice and the owner was very communicative. The whole process was super easy from booking to check in and out. All instructions were excellent. We cannot wait to go back. We highly recommend this property/owner! Great value too!"
Beautifully renovated 2 bedroom condo in Stratton VT - walk to Village/Lifts!

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

7.6 out of 10, Good, (53)
"Irish Bar nearby was a plus on St. Patrick’s Day !"
The price is SAR 199
SAR 969 total
includes taxes & fees
24 Apr - 25 Apr
Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails

Okemo's Jackson Gore-1 Bedroom Condo /Direct Ski Access. Walk to Pool & hot tubs

9.8 out of 10, Exceptional, (23)
"A quick trip with my son and took a chance on some spring skiing. While the weather was closer to summer than spring, our accommodations did not disappoint. Very roomy, comfortable and had everything, and then some, of what we needed. Excellent service by Jackson Gore and excellent communication with Alyson, our VRBO rep. Highly recommend and will be doing this again. "
Okemo's Jackson Gore-1 Bedroom Condo /Direct Ski Access. Walk to Pool & hot tubs

The Okemo Love Lounge

10.0 out of 10, Exceptional, (38)
"Fantastic location-out the back door onto the slope right next to the lift. Interior just as described. Host was super responsive and helpful. Would definitely stay again. "
The Okemo Love Lounge

Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street

9.0 out of 10, Wonderful, (21)
"We were in walking distance of restaurants. Close to Buttermilk Falls which was awesome! We went to Crowleys Cheese Factory, Green Mountain Sugar"
The price is SAR 184
SAR 862 total
includes taxes & fees
24 Apr - 25 Apr
Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street
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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Other property types in Chester

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3.0 star property
9.0 out of 10, Wonderful, (42)
"This property was perfectly situated for ski on ski off accessibility. It had plenty of room for four adults. We also enjoyed the Sauna after skiing. The host Ryan was very easy to deal with and the check in/out process was simple and efficient. "
Ski in & out Spruce Glen Townhomes on Great Eastern Trail

Your Vermont Mountain Haven Pet Friendly home with Hot tub!

9.8 out of 10, Exceptional, (18)
"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."
The price is SAR 759
SAR 2,415 total
includes taxes & fees
12 May - 13 May
Your Vermont Mountain Haven Pet Friendly home with Hot tub!

Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}

9.6 out of 10, Exceptional, (213)
"Cabin was beautiful! Love the little stream outside. Very close to restaurants, shopping, and hiking trails. "
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
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.

Frequently asked questions

How much do condos in Chester cost?
Condos in Chester range from SAR 184 to SAR 1,125 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 505 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.