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Next weekend

7 Rab. I - 9 Rab. I

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14 Rab. I - 16 Rab. I

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28 Rab. I - 30 Rab. I

In two months

25 Rab. II - 27 Rab. II

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

Standard Room, 2 Double Beds | Iron/ironing board, free WiFi, bed sheets

"Everyone was super friendly and very welcoming wonderful stay "

SAR 527 total

includes taxes & fees

10 Mar - 11 Mar

"Charming historic inn with incredibly good breakfast and dinner menu. Bakery also out of this world. Kids loved the library:game room and 24hr hot cocoa bar. Family owned- mother tubs inn and her children run the restaurant. Such a warm, lovely family. If you have trouble with stairs, may not be the best for you, but otherwise would stay again."

SAR 1,355 total

includes taxes & fees

3 Mar - 4 Mar

"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. "

SAR 588 total

includes taxes & fees

30 Mar - 31 Mar

"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."

SAR 617 total

includes taxes & fees

1 Apr - 2 Apr

"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...

SAR 584 total

includes taxes & fees

1 Apr - 2 Apr

1 bedroom, desk, iron/ironing board, free WiFi

"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."

SAR 626 total

includes taxes & fees

30 Mar - 31 Mar

"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...

"We had a wonderful visit with family and The Farmhouse offered a comfortable place for us to gather."

"During this season of gratitude we felt so lucky to stay at such a well appointed and lovely home. Unlike many rental homes that are stripped of personality, this home was full of charm and lovingly designed touches. From the cookware to the bedding the home was welcoming and comfortable. The kitchen and living room in particular were of good size for our entire group to eat and relax comfortably each with its own fireplace. "

Room, 2 Queen Beds Efficiency | Free WiFi

"Cute little motel. Basic but has what you need. Yummy muffins for breakfast too."

"Stayed here with friends for our annual ski trip. Spacious and comfortable."

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Other property types in Chester

"Loved being tucked away in the wilderness. Owners were very responsive. "

Condo, 2 Bedrooms | Pool | Outdoor pool, open 10:00 AM to 10:00 PM, sun loungers

"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. "

SAR 1,702 total

includes taxes & fees

1 Apr - 2 Apr

"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."

SAR 1,230 total

includes taxes & fees

12 Mar - 13 Mar

Recent reviews of Chester hotels

5/5 Excellent

"This place was adorable, and it was a very lucky find on the eve of a storm on a holiday weekend with 2 dogs in tow. Seems to be an old motel renovated. Cute decor. There were lots of cute helpful extras packed into a small space. Coffee, tea and Cider for the Keurig, retro mini fridge, garbage can with recyclables and compost sections, dog quilts. Self check in. Lot was frequently plowed during 24 hours of snow. Close to Killington and downtown Woodstock. Loved the 3pm check in and 11am checkout! Small things that were not ‘perfect’ were broken rack for hanging things near entry, some small garbage debris missed by housekeeping, and difficulty determining if I needed to contact Expedia or Sleep Woodstock with a question. All in all really came in clutch when we needed a clean and comfortable place close to mountain!"

A verified traveler stayed at Sleep Woodstock Motel

Posted 2 days ago

Frequently asked questions

How much do condos in Chester cost?

Condos in Chester range from SAR 240 to SAR 1,125 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 427 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.

Search Condo Rentals in Chester

Plan, book, stay with confidence

Check prices for these dates

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

Fullerton Inn

Stone Hearth Inn and Eatery

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

King & Queen Suite in Historic Inn Circa 1780

Room in Historic Inn! 20 Minutes to Okemo!

Honeymoon Suite with Jacuzzi Tub in Historic Inn

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

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

Rustic 150-year-old farmhouse, Jacuzzi included

Sprawling Riverbend Farmhouse Close to Mountains with Hot Tub

Motel in the Meadow

Stunning farmhouse-Historic village-Mins to Skiing

Other property types in Chester

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

Long Trail House at Stratton Mountain Resort

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

Recent reviews of Chester hotels

Sleep Woodstock Motel

Best Western Springfield Hotel

The Putney Inn

Fullerton Inn

Aspen At Manchester

Hampton Inn Brattleboro

Hampton Inn and Suites Manchester

Colonial Motel And Spa

Pointe at Castle Hill Resort

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