Search Guest Houses in Chester from CA $148

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Check prices for these dates

Next weekend
Apr 11 - Apr 13
In two weeks
Apr 18 - Apr 20
In one month
May 2 - May 4
In two months
May 30 - Jun 1

Browse Select Chester Guest Houses

Fullerton Inn
Standard Room, 2 Double Beds

Fullerton Inn

2.5 star property
8.0 out of 10, Very good, (344)
"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 CA $182
CA $198 total
includes taxes & fees
Apr 8 - Apr 9
Fullerton Inn
Stone Hearth Inn and Eatery
Front of property

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 CA $471
CA $514 total
includes taxes & fees
Apr 7 - Apr 8
Stone Hearth Inn and Eatery
Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!
Interior

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 CA $120
CA $221 total
includes taxes & fees
Apr 6 - Apr 7
Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!
King & Queen Suite in Historic Inn Circa 1780
Interior

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 CA $125
CA $232 total
includes taxes & fees
Apr 7 - Apr 8
King & Queen Suite in Historic Inn Circa 1780
Honeymoon Suite with Jacuzzi Tub in Historic Inn
1 bedroom, desk, iron/ironing board, free WiFi

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 CA $139
CA $235 total
includes taxes & fees
Apr 6 - Apr 7
Honeymoon Suite with Jacuzzi Tub in Historic Inn
Room in Historic Inn! 20 Minutes to Okemo!
Terrace/patio

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 CA $125
CA $219 total
includes taxes & fees
Apr 6 - Apr 7
Room in Historic Inn! 20 Minutes to Okemo!
1868 CARRIAGE HOUSE-QUAINT + COZY-LESS THAN 20 MIN TO OKEMO!
Exterior

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!
Sprawling Riverbend Farmhouse Close to Mountains with Hot Tub
Smart TV, fireplace, books, stereo

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
Exterior

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
Property grounds

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
Room, 2 Queen Beds Efficiency

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
Stunning farmhouse-Historic village-Mins to Skiing
Fridge, microwave, oven, stovetop

Stunning farmhouse-Historic village-Mins to Skiing

9.2 out of 10, Wonderful, (11)
"Stayed here with friends for our annual ski trip. Spacious and comfortable."
Stunning farmhouse-Historic village-Mins to Skiing
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, (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!!
Outdoor dining

Cozy Hideaway near Ludlow/Okemo. HOT TUB!!

9.8 out of 10, Exceptional, (204)
"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!!
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.