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

Fullerton Inn

2.5 star property
8.0 out of 10, Very Good, (345)
"Excellent service to help resolve reservation mix up. Small but serviceable room. Very limited breakfast. On premises restaurant was excellent for dinner"
The price is AED 474
AED 516 total
includes taxes & fees
10 Apr - 11 Apr
Fullerton Inn

Stone Hearth Inn and Eatery

3.0 star property
9.2 out of 10, Wonderful, (89)
"A historic establishment ran by a family, this cozy place in the mountains is a nice retreat from the daily hustle and bustle. "
The price is AED 1,218
AED 1,327 total
includes taxes & fees
10 Apr - 11 Apr
Stone Hearth Inn and Eatery

Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!

8.0 out of 10, Very Good, (1)
"Property seemed well-maintained and cared for. We were only there a short time, but it was well put together. The check-in process was a little hectic, check in time was 3pm, but our room wasn't ready. The caretaker was very friendly. We only had to wait about 20 minutes. We weren't aware this property was a VRBO, and not a regular Inn. "
The price is AED 312
AED 576 total
includes taxes & fees
10 Apr - 11 Apr
Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!

Honeymoon Suite with Jacuzzi Tub in Historic Inn

8.6 out of 10, Excellent, (7)
"I was enchanted to be staying in a beautiful antique decorated place. And the jacuzzi tub was large, comfortable, and easily accessed by a step."
The price is AED 364
AED 613 total
includes taxes & fees
10 Apr - 11 Apr
Honeymoon Suite with Jacuzzi Tub in Historic Inn

King & Queen Suite in Historic Inn Circa 1780

9.6 out of 10, Exceptional, (14)
"This is a fine place to stay. Everything is thoughtfully provided to make guests comfortable. The bed was very high quality, too. There were snacks, breakfast options, and good coffee available in the morning. Nothing fancy, but very useful and much appreciated."
The price is AED 327
AED 605 total
includes taxes & fees
10 Apr - 11 Apr
King & Queen Suite in Historic Inn Circa 1780

1868 CARRIAGE HOUSE-QUAINT + COZY-LESS THAN 20 MIN TO OKEMO!

9.6 out of 10, Exceptional, (36)
"We stayed for 20 days in January to enjoy skiing at Okemo, which was a short trip from the Carriage House. It was better than described on the listing with more amenities than expected. The kitchen was stocked with everything needed for cooking and baking-except for the groceries. The modern appliances and crockpot allowed me to cook with ease. Having a washer/dryer on site, as well as detergent, was very convenient. Hosts Jennifer and Michael provide a detailed description of how everything...
1868 CARRIAGE HOUSE-QUAINT + COZY-LESS THAN 20 MIN TO OKEMO!

Room in Historic Inn! 20 Minutes to Okemo!

9.4 out of 10, Exceptional, (13)
"I loved the room we stayed in. It was such a comfortable bed as well as the pillows. The bathroom was large and just about everything in our room was like a storybook. Loved skimming through some of the old books...so informative. The only thing I wished we knew is it was difficult to find a place to eat as we were there Monday thru Wednesday morning and no eateries on Main Street was opened. We drove a half our to eat breakfast. Perhaps it was the wrong season to go but the foliage was...
The price is AED 327
AED 572 total
includes taxes & fees
14 Apr - 15 Apr
Room in Historic Inn! 20 Minutes to Okemo!

Sprawling Riverbend Farmhouse Close to Mountains with Hot Tub

10.0 out of 10, Exceptional, (3)
"We loved staying in Amelia’s wonderful home! It was a short 20 min from Okemo ski resort and provided all of features we needed. Thank you for everything and for being so attentive!"
Sprawling Riverbend Farmhouse Close to Mountains with Hot Tub

Rustic 150-year-old farmhouse, Jacuzzi included

10.0 out of 10, Exceptional, (4)
"We had a wonderful visit with family and The Farmhouse offered a comfortable place for us to gather."
Rustic 150-year-old farmhouse, Jacuzzi included

Farmhouse w/ mountain views close to skiing. Includes outdoor sauna EV CHRGR

Farmhouse w/ mountain views close to skiing. Includes outdoor sauna EV CHRGR

Motel in the Meadow

2.5 star property
8.4 out of 10, Very Good, (71)
"Cute little motel. Basic but has what you need. Yummy muffins for breakfast too."
Motel in the Meadow

Beautiful farmhouse in Historic village

9.2 out of 10, Wonderful, (11)
"Stayed here with friends for our annual ski trip. Spacious and comfortable."
Beautiful farmhouse in Historic village
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, (42)
"This property was perfectly situated for ski on ski off accessibility. It had plenty of room for four adults. We also enjoyed the Sauna after skiing. The host Ryan was very easy to deal with and the check in/out process was simple and efficient. "
Ski in & out Spruce Glen Townhomes on Great Eastern Trail

Cozy Hideaway near Ludlow/Okemo. HOT TUB!!

9.8 out of 10, Exceptional, (205)
"Location was perfect. Cabin cute and comfortable. Pond was an amazing bonus with lots of cool birds. We had the best vacation there ever!"
Cozy Hideaway near Ludlow/Okemo. HOT TUB!!

Your Vermont Mountain Haven Pet Friendly home with Hot tub!

9.8 out of 10, Exceptional, (16)
"Family ski weekend. Our stay was very comfortable. Communication with host was phenomenal, always prompt and courteous Location is nice , very close to the ski resorts "
The price is AED 744
AED 2,365 total
includes taxes & fees
15 Apr - 16 Apr
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 AED 180 to AED 1,102 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.