Search Guest Houses in Chester from CA $175

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Browse Select Chester Guest Houses

The Burrell House

2.5 star property
9.6 out of 10, Exceptional, (123)
"We have a very sweet room that suits us fine. Is strange that we have not seen another person at this property since we have been here. No check in to speak of. Our friend is also staying here, and his room is essentially like a closet… so small. Close to town though, so very convenient"
The price is CA $189
CA $206 total
includes taxes & fees
Mar 16 - Mar 17
The Burrell House

The Inn At Quail Run

2.5 star property
9.0 out of 10, Wonderful, (64)
"Very nice "
The price is CA $311
CA $342 total
includes taxes & fees
Mar 4 - Mar 5
The Inn At Quail Run

The Weston

5.0 star property
10.0 out of 10, Exceptional, (7)
"The inn is beautiful and the service was exemplary. We asked for early check in and the staff was very accommodating. The room was very comfortable. We would love to visit again."
The price is CA $651
CA $709 total
includes taxes & fees
Mar 5 - Mar 6
The Weston

Ludlow Village Guest House - prime location on ski shuttle, walk to restaurants

9.8 out of 10, Exceptional, (40)
"My wife and I stayed here for 6 nights early February. The apartment is centrally located and had everything we needed. We walked everywhere. Minutes from the mountain, grocery store and restaurants. The building is small, but renovation was very well thought out. Absolutely no complaints. We look forward to booking here again. Thank you Craig and Diane!"
Ludlow Village Guest House - prime location on ski shuttle, walk to restaurants

Sutton's Place

2.5 star property
8.0 out of 10, Very good, (46)
"The owner is very nice. A lot of walkable dining options. "
Sutton's Place

Mountain cabin by skiing with fireplaces & well-equipped kitchen - dog-friendly

9.6 out of 10, Exceptional, (7)
"I had an excellent stay. The home was comfortable, clean, and very charming. The location was beautiful and private, and convenient to several nearby locations. I had no trouble checking in or out, and communications with the host were very easy."
Mountain cabin by skiing with fireplaces & well-equipped kitchen - dog-friendly

Ski SouthernVermont Getaway.

10.0 out of 10, Exceptional, (64)
"Great stay for our short snowboarding trip to Stratton. Very clean and quiet place. Terry was very responsive and accommodating for us. Would definitely consider staying here again if its available. Thanks! "
Ski SouthernVermont Getaway.

Inn at Clearwater Pond (Quechee)

3.5 star property
9.4 out of 10, Exceptional, (45)
"AMAZING STAY AMAZING PLACE"
Inn at Clearwater Pond (Quechee)

Renovated guest house. Min from Lake and Skiing.

10.0 out of 10, Exceptional, (2)
"This place was a pleasant surprise. Exactly what we were looking for. Thoroughly enjoyed this visit "
Renovated guest house. Min from Lake and Skiing.

Cozy, charming cottage 7 mins from Mount Snow and Lake Whitingham

10.0 out of 10, Exceptional, (11)
"Our 3rd stay at Josh's house was great. Perfect setup and location for a ski weekend. Josh is incredibly nice and communicative. Will be back next season."
Cozy, charming cottage 7 mins from Mount Snow and Lake Whitingham

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!

Magical Retreat Cottage - 15 min to Mt Snow - Ideal workcation

10.0 out of 10, Exceptional, (3)
"We enjoyed our stay. Being only 15 minutes from places to eat, we had total privacy and quiet. The surrounding forest and nearby river are great and make you feel like you have escaped somewhere. Plenty of room for a family of four with a loft and a private room. Living space was nicely setup. If you want to prep your own meals during a stay, this place has all that you would need. Coffee maker, grinder, and some coffee were there. A dishwasher was excellent. A washer and drier on site make it...
Magical Retreat Cottage - 15 min to Mt Snow - Ideal workcation

110 Deluxe Studio Queen on the 1st floor w/ outdoor heated pool

8.0 out of 10, Very good, (5)
"Beds not terrible. Sofa bed very terrible. Great pool. Reasanable price vs quality. Renovated in pass years. Clean place"
The price is CA $175
CA $257 total
includes taxes & fees
Mar 18 - Mar 19
110 Deluxe Studio Queen on the 1st floor w/ outdoor heated pool

Salt Ash Inn

3.0 star property
6.0 out of 10, (126)
"Great place, close proximity to Killington. Clean & quiet...Recommend this location."
Salt Ash Inn

Snow Goose Inn

2.5 star property
8.0 out of 10, Very good, (11)
"We booked this place as a bed and breakfast. No breakfast. No staff on site. No information was provided at the hotel to help us find things in the area. We were not informed that this was a "self check in hotel" until after the cancellation date. Calling the Heritage office (off site) for assistance was useless as the staff could not answer our questions. The common areas were sparsely furnished and shabby. The outside deck area hadn't been swept in quite a while. The deck furniture was in...
Snow Goose Inn
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

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

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 CA $528
CA $656 total
includes taxes & fees
Apr 1 - Apr 2
Long Trail House at Stratton Mountain Resort

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

9.2 out of 10, Wonderful, (67)
"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 CA $544
CA $970 total
includes taxes & fees
Mar 9 - Mar 10
Ski-in/out mountainside condo close to everything with full kitchen - tranquil
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.