Search and Rent Chester Condos

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Compare 379 Condo Rentals in Chester with updated reviews, rates, and availability.

Indoor pool, outdoor pool
SUNRISE 3BR - 2 Story Remodeled Condo - SKI ON & OFF. Pool + Trailside
10.0 out of 10, Exceptional, (151)
"Property has a great layout and the location was perfect. Would definitely book again."
SUNRISE 3BR - 2 Story Remodeled Condo - SKI ON & OFF. Pool + Trailside
Exterior
Slopeside Ski-On/Off Condo on Stratton. MNT access for hiking, biking, golf.
10.0 out of 10, Exceptional, (33)
"Great property. Spotless. Had everything we needed. Great information about the area. Bedroom configuration was perfect for us. Great ski on ski off location. Easy parking. Very responsive Host. Would definitely stay there again."
Slopeside Ski-On/Off Condo on Stratton. MNT access for hiking, biking, golf.
2 bedrooms, iron/ironing board, WiFi, bed sheets
Ski on ski off condo
10.0 out of 10, Exceptional, (57)
"chased great snow for Spring skiing at Stratton and worked remotely at night. Perfect. Quiet, convenient, clean and reasonably priced."
Ski on ski off condo
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Microwave, oven, stovetop, dishwasher
2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
10.0 out of 10, Exceptional, (76)
"Cute, cozy, and very clean space was perfect for a romantic getaway. Spacious common room and open kitchen amply stocked allowed us to cook in, as well as being centrally located so we just had to step out our door to walk to local restaurants and bars. Okemo mountain is just minutes away!"
The price is $99
$224 total
includes taxes & fees
May 6 - May 7
2 Bed Exceptional Fireplace Condo In the Heart of Town On Shuttle Route
Fridge, microwave, oven, stovetop
Ski-in/out condo with fireplace, pool, hot tub, sauna & washer/dryer
10.0 out of 10, Exceptional, (24)
"This is a beautiful ski in / ski out condo. The back porch is literally on the trail. Perfect location for our family to stop for a mid day snack and lunch break. The condo is exactly as described. We really loved the mud room for storing skis, boots, jackets, etc. We would def return to Okemo and stay here."
Ski-in/out condo with fireplace, pool, hot tub, sauna & washer/dryer
Interior
Ski Haven: 1-Bed Condo, Okemo Base Area Retreat
10.0 out of 10, Exceptional, (4)
"great condo and location and well equipped kitchen."
Ski Haven: 1-Bed Condo, Okemo Base Area Retreat
Property grounds
⭐️Ski On-Ski Off Cozy Mountain Condo w/Real Wood Fire Place- King Bed 2-Bed/Bath
10.0 out of 10, Exceptional, (57)
"Perfect condo for our stay. Easy to get around the area and a very short walk to the slopes - we’ll be back!"
⭐️Ski On-Ski Off Cozy Mountain Condo w/Real Wood Fire Place- King Bed 2-Bed/Bath
Indoor pool, a heated pool
Seasons On Mount Snow - Ski-in/Ski-out
9.8 out of 10, Exceptional, (148)
"Carl was super nice, proactive, and a great communicator for this trip. The place was convenient, clean, in great repair, with lots of amenities and super easy to ski out. Little touches like a box of firewood, tinder, and matches and clear instructions on everything make things so pleasant. Would totally stay again. "
Seasons On Mount Snow - Ski-in/Ski-out
TV, fireplace
Ski-in/out condo with a pool, fireplace & fast WiFi - Sachem Trail at Okemo
9.8 out of 10, Exceptional, (22)
"Clean, convenient and cozy. Would stay there again."
Ski-in/out condo with a pool, fireplace & fast WiFi - Sachem Trail at Okemo
Fridge, microwave, oven, stovetop
Recently Renovated Ski-In/Out Condo w/Fireplace, Shared Pool, Hot Tub, Sauna
9.8 out of 10, Exceptional, (18)
"Great location, very close to ski lifts. House was clean, spacious and cozy with everything you need."
Recently Renovated Ski-In/Out Condo w/Fireplace, Shared Pool, Hot Tub, Sauna
Smart TV, fireplace, stereo
Condo #5 Slopeside One Bedroom with Hot Tub
9.8 out of 10, Exceptional, (21)
"This was the perfect spot for us with our infant and dog. The location was great for us (we both wanted to ski but someone always had to be on baby duty, so being right on the resort was wonderful). We made all our meals onsite and found the kitchen fully stocked for our needs. Our evenings were spent watching March Madness through the window while in the hot tub with the baby monitor close by."
Condo #5 Slopeside One Bedroom with Hot Tub
TV, fireplace
Inviting condo with skiing, pool, hot tub, tennis, fireplace & W/D
9.8 out of 10, Exceptional, (10)
"Very clean and nice condo, comfortable, well equipped kitchen. For our needs perfectly. Love the Sunrise Village area at Killington."
Inviting condo with skiing, pool, hot tub, tennis, fireplace & W/D
Outdoor pool, a heated pool
5 minute walk to lifts and Stratton Village! Cozy fireplace with a private patio
9.6 out of 10, Exceptional, (8)
"Great place. Super close to everything. Host was super helpful. Everything you need for an amazing ski weekend."
5 minute walk to lifts and Stratton Village! Cozy fireplace with a private patio
Property grounds
Ski-in/out condo with patio, full kitchen & high-speed WiFi
9.4 out of 10, Exceptional, (19)
"Enjoy our stay !!!!! Awesome in and out right on the slope feet away for deck."
The price is $153
$403 total
includes taxes & fees
May 5 - May 6
Ski-in/out condo with patio, full kitchen & high-speed WiFi
TV, fireplace
Ski-in/out condo with mountain views, fireplace, hot tub, pool, & tennis
9.4 out of 10, Exceptional, (24)
"The kids (ages 3, 4, 5 and 6) had a blast, and it was amazing that they could play outside in the snow right outside the backdoor."
Ski-in/out condo with mountain views, fireplace, hot tub, pool, & tennis
Outdoor dining
Ski-in/out Condo on Bull Run Trail with fireplace, & full kitchen
9.4 out of 10, Exceptional, (72)
"Highly recommend renting this condo for a true ski on/ski off experience. Yes, the condo is dated but it is clean and well appointed and you can't beat the location on the mountain. We had an excellent experience and will certainly rent here again. Thank you, Vacasa for making check in and check out very easy!"
Ski-in/out Condo on Bull Run Trail with fireplace, & full kitchen
Property grounds
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
9.2 out of 10, Wonderful, (19)
"Great location! Has everything you need! "
The price is $52
$240 total
includes taxes & fees
May 5 - May 6
Ski-In/Out condo with patio, mountain views, washer/dryer, & cable
Sunrise Mountain Village - West Glade J-1- Ski in-Ski Out
9.0 out of 10, Wonderful, (14)
"We were only in town for 2 days for the solar eclipse. We all wished we were staying longer. Please highlight for guests that the code for the door lock stops working right at 10am - we"
Sunrise Mountain Village - West Glade J-1- Ski in-Ski Out
TV, fireplace, DVD player
Mountain view condo with fireplace, pool, hot tub, tennis, washer/dryer & cable
9.0 out of 10, Wonderful, (18)
"This was a nice condo, suited our family's needs for a weekend getaway."
Mountain view condo with fireplace, pool, hot tub, tennis, washer/dryer & cable
Fridge, microwave, oven, stovetop
Ski-In/ski-out condo with mountain view, pools, hot tub & gym
9.0 out of 10, Wonderful, (73)
"Beautiful condo, clean and private, good location!"
Ski-In/ski-out condo with mountain view, pools, hot tub & gym
Don't see what you're looking for?
See all available properties in Chester
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.

Other property types in Chester

Fridge, microwave, oven, stovetop
Lakefront house with skiing nearby, dock, and amazing views - dog-friendly
9.6 out of 10, Exceptional, (29)
"Two families stayed for a ski trip to okemo. Proximity to the mountain was a big plus for us. The cabin is cozy."
Lakefront house with skiing nearby, dock, and amazing views - dog-friendly
Exterior
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
9.6 out of 10, Exceptional, (176)
"Third time as good as the first. We will return next year"
Beautiful Honeymoon Cottage close to Manchester Vermont. {Manchester Center}
Interior
Secluded dog-friendly chalet in the woods w/fireplace, jetted tub, deck, & grill
9.4 out of 10, Exceptional, (47)
"We loved our stay at the chalet. It's perfectly situated in the cutest little neighborhood, while also feeling very secluded. The chalet had everything we needed for our stay. While visiting we walked a few of the trails nearby, part of the Valley Trail and the Hoot, Toot and Whistle. They were both perfect for our pups, especially during hunting season. We gave our pups an extra squeeze in honor of Scarlet. Thank you for sharing your place with us! We would love to stay again!!"
Secluded dog-friendly chalet in the woods w/fireplace, jetted tub, deck, & grill
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.

Chester Condo Rentals information

Number of reviews
668
Accommodation
379 Condo Rentals
Lowest Price
$52
Highest Price
$153

Frequently asked questions

How much do condos in Chester cost?
The price range for condos in Chester is $52 to $153 per night. No matter your budget, you’ll find a place that fits your needs — as well as your entire squad! This price was 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.
Why book your condo in Chester with Expedia?
Booking a condo in Chester is as simple as deciding on your travel dates and selecting an option that suits your style. Looking for something upscale or budget friendly, or a stay that also has a kitchen and laundry? Use Expedia’s search filters to further narrow your search results and find your dream fit.
How can I find cheap condos in Chester?
The simplest way to compare cheap condos in Chester is with Expedia’s handy filter tool. Refine your search by budget, amenities and star rating to land awesome rates in just a few keystrokes.
What is there to do in Chester near my condo?
Once you’ve unpacked your bags, set out and discover the wonderful things Chester has for you to experience. DaVallia Art & Accents is a top attraction to add to your itinerary.

Recent reviews of Chester hotels
Expedia verified reviews

The Shire Woodstock

The Shire Woodstock

5/5 Excellent
"Outstanding "
A verified traveler stayed at The Shire Woodstock
Posted 6 hours ago
The Shire Woodstock