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Check prices for these dates

Next weekend
28 Feb - 2 Mar
In two weeks
7 Mar - 9 Mar
In one month
21 Mar - 23 Mar
In two months
18 Apr - 20 Apr

Compare 427 Condo Rentals in Chester with updated reviews, rates, and availability.

Walk to Mount Snow, Cozy, Clean and Comfortable!
Exterior

Walk to Mount Snow, Cozy, Clean and Comfortable!

9.6 out of 10, Exceptional, (33)
"Nice place for a short ski trip. Convenient shuttle to mountain. The property manager was very responsive to requests and the weekend was perfect"
Walk to Mount Snow, Cozy, Clean and Comfortable!
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities

Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities

8.6 out of 10, Excellent, (24)
"The apartment was in a great location to get to the ski lifts. "
The price is AED 279
AED 1,066 total
includes taxes & fees
27 Feb - 28 Feb
Ski-in/ski-out condo with deck, wood-burning fireplace, & community amenities
SUNRISE 3BR - 2 Story Remodeled Condo - SKI ON & OFF. Pool + Trailside
Interior

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

10.0 out of 10, Exceptional, (165)
"Very nice property and location. Unit had everything we needed. Nicely laid out for our family. Owners were very responsive. "
SUNRISE 3BR - 2 Story Remodeled Condo - SKI ON & OFF. Pool + Trailside
Walk-to-A/B Quad, Winterplace condo with hot tubs, indoor pool, fireplace & wifi

Walk-to-A/B Quad, Winterplace condo with hot tubs, indoor pool, fireplace & wifi

Walk-to-A/B Quad, Winterplace condo with hot tubs, indoor pool, fireplace & wifi
Cozy Mountain Condo with Ski-In/Ski-Out Access, and Electric Fireplace

Cozy Mountain Condo with Ski-In/Ski-Out Access, and Electric Fireplace

Cozy Mountain Condo with Ski-In/Ski-Out Access, and Electric Fireplace
Escape to This Mountain Retreat Near Hiking Trails, Pools, and Golf Courses
Living area

Escape to This Mountain Retreat Near Hiking Trails, Pools, and Golf Courses

10.0 out of 10, Exceptional, (8)
"My husband, daughter and I had a wonderful long weekend at William's cabin. It was incredibly cozy and spacious. We enjoyed our evenings by the fire after a long day of skiing. It was an easy check in and check out process. William is a wonderful host! I would highly recommend renting this cabin for a cozy getaway to Stratton."
Escape to This Mountain Retreat Near Hiking Trails, Pools, and Golf Courses
Cozy 3 bedroom condo 2.5 miles to Mount Snow
Living area

Cozy 3 bedroom condo 2.5 miles to Mount Snow

9.2 out of 10, Wonderful, (36)
"We loved the place. It was very homey and comfortable. My only suggestion would be to upgrade the towels and add a few more dish towels. "
The price is AED 367
AED 1,129 total
includes taxes & fees
4 Mar - 5 Mar
Cozy 3 bedroom condo 2.5 miles to Mount Snow
8 Guest 3BR, 2 BA Stratton Condo with Fireplace and forest views.
Living area

8 Guest 3BR, 2 BA Stratton Condo with Fireplace and forest views.

10.0 out of 10, Exceptional, (10)
"We had a wonderful, excellent stay at this place. It's only few minutes of drive from Stratton Mountain. The kitchen was equipped with all necessary modern clean appliances, utensils all were in a perfect condition. The bathrooms were super clean with nice quality shampoo, conditioner. The bed sheets were crispy and clean. Everything we needed was there and exceeded our expectations - huge TV with multiple streaming apps, board games, plenty of dry firewood, state of art thermostats to adjust...
8 Guest 3BR, 2 BA Stratton Condo with Fireplace and forest views.
Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails

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

7.6 out of 10, Good, (50)
"This cozy cabin was perfect for a ski weekend with friends. We really enjoyed gathering by the stone fireplace after a couple long days out on the slopes."
The price is AED 393
AED 1,187 total
includes taxes & fees
26 Feb - 27 Feb
Condo with Seasonal Pool & Tennis Courts - Walk to Ski Trails
Updated Ski in ski out condo & mountain biking located at Seasons on Mt. Snow
Interior

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

10.0 out of 10, Exceptional, (51)
"Really loved the location of this property! Ski on/ski off was amazing! The property was great, exactly as pictured and we would love staying here again in the future!"
Updated Ski in ski out condo & mountain biking located at Seasons on Mt. Snow
Okemo Mountain Retreat: 3BR Ski-in/Ski-Out Condo

Okemo Mountain Retreat: 3BR Ski-in/Ski-Out Condo

10.0 out of 10, Exceptional, (11)
"Thanks for the lodging. Had a great time getting some turns on the mountain. Hopefully be able to come back soon "
Okemo Mountain Retreat: 3BR Ski-in/Ski-Out Condo
Newly renovated ski-in/out slope side condo

Newly renovated ski-in/out slope side condo

8.8 out of 10, Excellent, (19)
"Clean, and close to clock tower base "
Newly renovated ski-in/out slope side condo
Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort
Living area

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

10.0 out of 10, Exceptional, (17)
"Amazing place! "
The price is AED 1,286
AED 2,189 total
includes taxes & fees
28 Feb - 1 Mar
Beautiful Condominium at Castle Hill Resort, 10 Minutes from Okemo Ski Resort
Roomy ski condo next to Mt. Snow, on the mover bus, with hot tub and sauna!
Living area

Roomy ski condo next to Mt. Snow, on the mover bus, with hot tub and sauna!

10.0 out of 10, Exceptional, (4)
"This was the perfect ski condo for two families-everything we needed, close to the mountain. We would definitely rent again."
Roomy ski condo next to Mt. Snow, on the mover bus, with hot tub and sauna!
Ski-in/out condo with a fireplace, hot tub, gym, pool, washer/dryer & cable

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
Now avail PRIME Feb Weekend - Fri Feb 21 - Sun Feb 23
Property grounds

Now avail PRIME Feb Weekend - Fri Feb 21 - Sun Feb 23

10.0 out of 10, Exceptional, (29)
"Perfect location. Well cared for, nicely updated and a super host ."
The price is AED 2,571
AED 4,175 total
includes taxes & fees
24 Feb - 25 Feb
Now avail PRIME Feb Weekend - Fri Feb 21 - Sun Feb 23
Ski-in/out mountainside condo close to everything with full kitchen - tranquil

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

9.2 out of 10, Wonderful, (66)
"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 AED 294
AED 1,022 total
includes taxes & fees
24 Feb - 25 Feb
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
Lovely ski-in/out condo steps from ski lift with trails and amazing views

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

8.8 out of 10, Excellent, (22)
"Unit is very close to ski lift. Ski in / ski out was great!!!"
The price is AED 279
AED 1,057 total
includes taxes & fees
24 Feb - 25 Feb
Lovely ski-in/out condo steps from ski lift with trails and amazing views
Charming 3BR/2BA Condo in Sunrise Village at Killington. Pool. Hot Tub. Sports Center.
Cozy living room of the Sunrise Timberline ski-in ski-out rental condo in Killington, VT, featuring a large L-shaped sofa, a balcony and a high window showing mountain views, and an exposed-brick wall with a 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. "
Charming 3BR/2BA Condo in Sunrise Village at Killington. Pool. Hot Tub. Sports Center.
Snow Mtn Escape-Shuttle to Mt.Snow w/ Indoor Pool!

Snow Mtn Escape-Shuttle to Mt.Snow w/ Indoor Pool!

Snow Mtn Escape-Shuttle to Mt.Snow w/ Indoor 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.
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Other property types in Chester

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

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

10.0 out of 10, Exceptional, (22)
"Loved being tucked away in the wilderness. Owners were very responsive. "
Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area
Long Trail House at Stratton Mountain Resort
Living room

Long Trail House at Stratton Mountain Resort

3.0 star property
8.4 out of 10, Very Good, (72)
"Condo was great, cozy, and clean. Has access to the pool and hot tubs from back porch and has great Mountain View’s. The village had plenty of food, little expensive, but pretty good. Overall great place to stay and enjoy the mountain. "
The price is AED 1,451
AED 1,803 total
includes taxes & fees
25 Mar - 26 Mar
Long Trail House at Stratton Mountain Resort
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Front of property

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
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 AED 279 to AED 2,571 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 427 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.