Search Condo Rentals in Chester

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Compare 399 Condo Rentals in Chester with updated reviews, rates, and availability.

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

9.2 out of 10, Wonderful, (19)
"Many years ago my husband and I had summer access to an identical condo to this one in Solitude Village on Mt. Okemo, so this past week was a real walk down memory lane! The condo was lovely…very clean and well appointed, with sweeping views of the mountains from the master bedroom and living room. The king mattress was very comfortable, and the numerous linens available were fresh, plentiful and high-end. The grounds of Solitude were exquisitely maintained, and while these units do not have AC,...
Ski-in/out condo with pool, 2 hot tubs, sauna - short walk to Solitude clubhouse

Ski On & Off 2 BR Okemo Solitude Village Condo

10.0 out of 10, Exceptional, (24)
"We had a wonderful weekend ski trip with our teenage daughter. The condo is beautiful, very well appointed and just a short walk across the parking lot to the ski trail. We love the location of Solitude Village, so easy to access the entire mountain. We would definitely come back!"
Ski On & Off 2 BR Okemo Solitude Village Condo

Stratton Mountain, Nearly Ski In/Ski Out, Obertal C Building, 2 Bedrooms, 1 Bath

9.8 out of 10, Exceptional, (151)
"Frequent renter of this condo, everything about it is great; location, cleanliness, responsiveness of owner, etc."
Stratton Mountain, Nearly Ski In/Ski Out, Obertal C Building, 2 Bedrooms, 1 Bath

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

8.4 out of 10, Very Good, (52)
"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

Ski on ski off condo

10.0 out of 10, Exceptional, (62)
"We came to Stratton for the 29029 event. We have both participated before and this year we’re volunteering. We knew we wanted to stay close to the base lodge and this was the perfect location - an easy 10 minute walk. The condo was clean and we really liked having a fulll kitchen and washer/dryer. The shower was great after spending 8 hours at the summit - great water pressure and loved the rain shower head! Would definitely book again!"
Ski on ski off condo

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

9.2 out of 10, Wonderful, (64)
"Was supposed to be first floor but had to go up lots of stairs. The place was very clean but dated. Better for young people not good for old people."
The price is SAR 293
SAR 1,056 total
includes taxes & fees
26 Nov - 27 Nov
Ski-in/out mountainside condo close to everything with full kitchen - tranquil

Walk to Mount Snow, Cozy, Clean and Comfortable!

9.6 out of 10, Exceptional, (29)
"Upon reserving the property, I sent an email to the owner and requested an early checkin, he responded very quickly and accomodated my request. The check in process was very easy, and the property was very clean. The only issue was the hot tub was not installed and functioning dury my stay, which I specifically asked for. The inside of the condo was very clean and the owner provided everything you needed. The only downside was the outside of the property was a little run down and needed some...
Walk to Mount Snow, Cozy, Clean and Comfortable!

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

9.8 out of 10, Exceptional, (157)
"This was possibly one of the best VRBO experiences for me. Flawless in all respects"
Seasons On Mount Snow - Ski-in/Ski-out

Slopeside Ski-On/Off Condo on Stratton. MNT access for hiking, biking, golf.

10.0 out of 10, Exceptional, (37)
"Thank you so much for a great stay! "
Slopeside Ski-On/Off Condo on Stratton. MNT access for hiking, biking, golf.

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

9.8 out of 10, Exceptional, (40)
"Well appointed and perfect location - would definitely stay again"
Ski-in/out condo with water & mountain views, private sauna & fireplace

Updated Ski in ski out condo & mountain biking located at Seasons on Mt. Snow

10.0 out of 10, Exceptional, (45)
"Great location, cute condo, very clean."
Updated Ski in ski out condo & mountain biking located at Seasons on Mt. Snow

⭐️Ski On-Ski Off Cozy Mountain Condo w/Real Wood Fire Place- King Bed 2-Bed/Bath

10.0 out of 10, Exceptional, (61)
"Great location and nice views - caught sunrise and sunset. plenty of parking. Owner was easy to reach and responded quickly."
⭐️Ski On-Ski Off Cozy Mountain Condo w/Real Wood Fire Place- King Bed 2-Bed/Bath

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

9.4 out of 10, Exceptional, (33)
"Great condo for family fun and skiing. We would definitely stay again!"
Condo near ski trail with fireplace, hot tub, pool, tennis & washer/dryer

Renovated Luxury 4 Bedroom 3.5 Bath Okemo Trailside

10.0 out of 10, Exceptional, (23)
"We were awestruck when we entered the property and saw the view of mountains and cloud. Liked the interior and blend of contemporary as well as traditional designs inside. Had a lovely stay and Robert is the best and most transparent host I have ever experienced."
Renovated Luxury 4 Bedroom 3.5 Bath Okemo Trailside

Stratton 1 Bedroom Long Trail Condo, Walk to Village and Lifts

9.6 out of 10, Exceptional, (45)
"Great location to mountain and village. Small room but great for a family of 4- (kids only 6 and 8). Will grow out of this space with older kids. Great proximity to pool too! Loved it."
Stratton 1 Bedroom Long Trail Condo, Walk to Village and Lifts

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

8.6 out of 10, Excellent, (4)
Ski-in/ski-out condo with resort amenities and mountain views

Magic Mountain Trailside Condo - Ski In / Ski Out

9.8 out of 10, Exceptional, (10)
"This was the perfect spot for my wife and I for a 2 night stay while attending a wedding on the mountain. The condo was clean and had everything needed for us to enjoy the weekends festivities. "
The price is SAR 469
SAR 1,188 total
includes taxes & fees
26 Nov - 27 Nov
Magic Mountain Trailside Condo - Ski In / Ski Out

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

9.6 out of 10, Exceptional, (11)
"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

Modern & Updated Winterplace 3Br- Sleeps 12 by RedAwning

7.4 out of 10, Good, (3)
"I have booked with VRBO for years. The booking said Ski in and out with a renovated surroundings. First … walking down 2 flights of stairs icy wooden walkway , across a icy parking lot, up a bank of snow and down in ski boots is not what I call ski in and out. Close to slopes is one thing! Second, my family cooks in for meals. The pots and pans were dirty and awful. Didn’t have enough silverware or glasses! Mattresses in master and second bedroom were old and uncomfortable. The unit was ok but...
Modern & Updated Winterplace 3Br- Sleeps 12 by RedAwning

Ski-in/ski-out home with a private hot tub, dry sauna, wood fireplace, & balcony

Ski-in/ski-out home with a private hot tub, dry sauna, wood fireplace, & balcony
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, (39)
"Everything was wonderful. Easy in and out. Near to almost everything. Beautiful area. I left my keys by mistake and they were wonderful in getting them back to me. I would stay there again. "
Ski in & out Spruce Glen Townhomes on Great Eastern Trail

Cozy Hideaway near Ludlow/Okemo. HOT TUB!!

9.8 out of 10, Exceptional, (196)
"It was a wonderful little cabin that was clean and decorated comfortably. It had everything we needed. The hot tub was delightful! "
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!

Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, Trim a Tree! 45% Off! Free Pool

9.8 out of 10, Exceptional, (164)
"The property is exactly like the pictures indicate. The house is in a friendly neighborhood outside of town. The house is very comfortable and spacious. The host responds to your messages in timely manner, and, she is very workable. Would definitely stay there again "
Luxury Log Home, 6 BR 4BA, Pool Table, Hot Tub, Trim a Tree! 45% Off! Free Pool
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?
Expect to pay from SAR 293 to SAR 469 per night for condos in Chester. No matter your budget, an epic stay is a click away on Expedia. 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?
Make use of your vacation days and choose from 399 condos in Chester. For work-related travel, a solo adventure and everything in between, Expedia will help you find the perfect space in just a click or two.
Why book your condo in Chester with Expedia?
Expedia makes it easy to find your dream condo in Chester. On the lookout for a luxury stay? Try out our filters to search for properties with a 5-star rating. If you have a fixed budget, click on how much you’d like to spend and then browse our fabulous deals. We’ll help you find the right place whatever your trip looks like.
How can I find cheap condos in Chester?
The easiest way to compare cheap condos in Chester is with Expedia’s easy-to-use filter tool. Refine your search by star rating, amenities and budget to secure awesome prices in just a few clicks.