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Check prices for these dates

Next weekend
4 Apr - 6 Apr
In two weeks
11 Apr - 13 Apr
In one month
25 Apr - 27 Apr
In two months
23 May - 25 May

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

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, (164)
"Wonderful host / fantastic location "
The price is AED 643
AED 818 total
includes taxes & fees
26 Mar - 27 Mar
Seasons On Mount Snow - Ski-in/Ski-out
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, (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
Fridge, microwave, oven, stovetop

Ski-in/out condo with a fireplace, hot tub, gym, pool, washer/dryer & cable

8.2 out of 10, Very Good, (19)
"Place and location were good. That said management company never sent our check information. Apparently they had sent separate email that required ID verification and was deleted as I thought it was spam. I completely understand why this would be helpful but has never been required at any place I've stayed before. The problem is that this was never communicated in the text I received day prior or with booking email. When I realized I had received no checkin details it then took over 1.5 hrs...
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
Exterior

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 AED 1,102
AED 1,966 total
includes taxes & fees
30 Mar - 31 Mar
Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
Property grounds

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

9.0 out of 10, Wonderful, (70)
"Unit is comfortable, clean and very accessible to the Clock tower base of Okemo mtn for skiing. That's why you choose this unit. It definitely can use some updates and general maintenance. Items homeowner could address:Shower drainage issues, several lightbulbs need changing, add some cutlery (There should be enough spoons to cover the amount of people the unit can accomodate), Update lockbox and the door lock on ski closet. "
The price is AED 275
AED 970 total
includes taxes & fees
7 Apr - 8 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 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
9.8 out of 10, Exceptional, (6)
"Everything was excellent. 3 baths 3 beds. Perfect. Bring coffee filters and hangers."
Ski In/Out Sunrise West Glade 3 BR 3 BA Trailside, Sauna, Pool, Hot Tub
Mountain-view condo with private balcony, fireplace, & updated interior
Snow and ski sports

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

8.2 out of 10, Very Good, (13)
"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
Fridge, microwave, oven, stovetop

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

8.2 out of 10, Very Good, (11)
"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
Interior

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
Fridge, microwave, oven, stovetop

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

8.4 out of 10, Very Good, (55)
"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
Interior

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

8.6 out of 10, Excellent, (46)
"Location with access to slopes was exceptional! The condo itself was cozy and inviting. Everything necessary was provided for the duration of the stay. Would stay again! Cheers"
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
Fridge, microwave, oven, stovetop

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

9.4 out of 10, Exceptional, (35)
"Perfect condo for a ski weekend to celebrate our son's birthday. Bunk beds were perfect for 4 active boys. Location was also perfect. Condo was well appointed and exactly as advertised. We will be back!"
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.
Smart TV, fireplace

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

10.0 out of 10, Exceptional, (1)
"We had a special ski weekend with friends. "
The price is AED 1,010
AED 2,568 total
includes taxes & fees
27 Mar - 28 Mar
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
TV, fireplace

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 AED 261
AED 1,019 total
includes taxes & fees
7 Apr - 8 Apr
Lovely ski-in/out condo steps from ski lift with trails and amazing views
Stratton Mtn Studio | Renovated | Walk to Lifts
Exterior

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 AED 643
AED 1,536 total
includes taxes & fees
13 Apr - 14 Apr
Stratton Mtn Studio | Renovated | Walk to Lifts
Beautifully renovated 2 bedroom condo in Stratton VT - walk to Village/Lifts!
Exterior

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

10.0 out of 10, Exceptional, (11)
"Amazing condo and the location can’t be beat! Thanks!"
Beautifully renovated 2 bedroom condo in Stratton VT - walk to Village/Lifts!
Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
Fridge, microwave, oven, stovetop

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

7.6 out of 10, Good, (52)
"Irish Bar nearby was a plus on St. Patrick’s Day !"
The price is AED 195
AED 935 total
includes taxes & fees
7 Apr - 8 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
Indoor pool, outdoor pool

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

9.8 out of 10, Exceptional, (23)
"This was our third time skiing at Okemo and was without doubt the best. Access to the slopes is so easy and the unit itself is top notch. Loved everything about it! "
Okemo's Jackson Gore-1 Bedroom Condo /Direct Ski Access. Walk to Pool & hot tubs
The Okemo Love Lounge
Fridge, microwave, oven, dishwasher

The Okemo Love Lounge

10.0 out of 10, Exceptional, (37)
"Hi Everything was as described in listing. Lots of amenities son kitchen as well as in bathroom. Place was very clean. Only feedback is that front door lock is very hard to open and area rugs were curling up in the sides so we moved them out of the walking area. I would stay again. Perfect location. "
The price is AED 1,377
AED 2,106 total
includes taxes & fees
26 Mar - 27 Mar
The Okemo Love Lounge
Downtown Condo w/ Electric Fireplace, WiFi & Shuttle Stop Across the Street
Interior

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 AED 180
AED 848 total
includes taxes & fees
7 Apr - 8 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

Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area
Miscellaneous

Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area

10.0 out of 10, Exceptional, (23)
"This lovingly built off-grid glamping cabin is drenched with sun! It’s absolutely gorgeous! The kids enjoyed pumping their own water and sledding down the front hill. Paris is an excellent hostess- she answered all our questions very promptly & thoroughly. We cant wait to come back! Thank you!!!"
Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Fridge, microwave, oven, stovetop

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3.0 star property
9.0 out of 10, Wonderful, (41)
"very clean and easy to access close to mountain"
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Long Trail House at Stratton Mountain Resort
Condo, 2 Bedrooms | Pool | Outdoor pool, open 10:00 AM to 10:00 PM, sun loungers

Long Trail House at Stratton Mountain Resort

3.0 star property
8.6 out of 10, Excellent, (74)
"Nice, clean room in prime location"
The price is AED 1,267
AED 1,575 total
includes taxes & fees
13 Apr - 14 Apr
Long Trail House at Stratton Mountain 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.

Frequently asked questions

How much do condos in Chester cost?
Condos in Chester range from AED 180 to AED 1,377 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.
How can I find cheap condos in Chester?
Expedia can help you look for cheap condos in Chester. To book your ideal stay in a few clicks, try out our handy filter tool to refine your search results by star rating, amenities and budget.