Search and Rent Chester Condos

  • Plan, book, stay with confidence

    • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    one key icon
    Treat yourself
    Save instantly and earn perks with One Key
    Learn about One Key
    today icon
    Change your mind
    Book hotels with free cancellation

Check prices for these dates

Next weekend
May 9 - May 11
In two weeks
May 16 - May 18
In one month
May 30 - Jun 1
In two months
Jun 27 - Jun 29

Compare 514 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)
"My friends and I stayed here for a wedding, and it was the perfect location for us! Easy to find and check in, with all the necessary amenities. I would highly recommend this rental for anyone looking to stay in the area!"
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 with trail access. The pool, sauna and steam room were great. Very clean and very convenient. Owners were very responsive and helpful."
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)
"We came back for a second time because we loved this place so much! Spectacular views, well-furnished, great layout for families and a very pleasant stay!"
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)
"Amazing place! "
The price is $539
includes taxes & fees
$481 per night
May 1 - May 2
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, (72)
"Dated but well appointed and comfortable condo. Be prepared for lots of stairs but great location directly slopeside."
The price is $251
includes taxes & fees
$224 per night
May 1 - May 2
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, (7)
"Excellent location"
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

7.8 out of 10, Good, (14)
"Spent only one due the dirty conditions and red spot on the sheets "
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

8.4 out of 10, Very Good, (14)
"great condo pool nice and quiet "
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)
"This was a great place to stay. Clean, spacious, and gorgeous. I love the fully stocked kitchen, the games for the family, and relaxing spa like bathrooms."
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, (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
Interior

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

8.6 out of 10, Excellent, (47)
"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, (36)
"Loved access to the pool"
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.

9.0 out of 10, Wonderful, (2)
"We had a special ski weekend with friends. "
The price is $621
includes taxes & fees
$550 per night
May 1 - May 2
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)
"We loved staying at the townhome. It was a welcome place to stay while we traveled around, enjoying fall. It was very comfortable and the village amenities were great."
The price is $279
includes taxes & fees
$247 per night
May 1 - May 2
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)
"Great location."
The price is $373
includes taxes & fees
$331 per night
May 1 - May 2
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)
"Great time and perfect locationEverything you need for a Stratton get away"
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, (53)
"Irish Bar nearby was a plus on St. Patrick’s Day !"
The price is $260
includes taxes & fees
$233 per night
May 1 - May 2
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)
"We loved the location with ski slopes right out the door and the hot tubs were perfect after a full day outside"
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, (38)
"Place was great, location was incredible and communication with host was great "
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 $217
includes taxes & fees
$194 per night
May 11 - May 12
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.
Don't see what you're looking for?
See all available properties in Chester
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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)
"Peaceful vacation"
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, (42)
"Very nice place only negative was the sauna did not work"
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
Outdoor spa tub

Your Vermont Mountain Haven Pet Friendly home with Hot tub!

9.8 out of 10, Exceptional, (18)
"This place was absolutely perfect and wonderful. It offered a cozy family getaway to enjoy the southern Vermont scene that we have grown to love so very much. The house and owner are absolutely amazing and we hope to stay here again for our trips back to this area. Highly recommend! "
The price is $644
includes taxes & fees
$574 per night
May 1 - May 2
Your Vermont Mountain Haven Pet Friendly home with Hot tub!
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 $217 to $621 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 514 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.