Search Guest Houses in Chester from CA $310

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Check prices for these dates

Next weekend
Feb 7 - Feb 9
In two weeks
Feb 14 - Feb 16
In one month
Feb 28 - Mar 2
In two months
Mar 28 - Mar 30

Browse Select Chester Guest Houses

The Burrell House
Exterior

The Burrell House

2.5 star property
9.6 out of 10, Exceptional, (122)
"Really enjoyed it. Quaint area, great room and friendly service!"
The Burrell House
The Inn At Quail Run
Seasonal outdoor pool

The Inn At Quail Run

2.5 star property
9.0 out of 10, Wonderful, (64)
"Very nice "
The price is CA $310
CA $341 total
includes taxes & fees
Feb 4 - Feb 5
The Inn At Quail Run
The Weston
Front of property

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 $648
CA $706 total
includes taxes & fees
Feb 2 - Feb 3
The Weston
Ludlow Village Guest House - prime location on ski shuttle, walk to restaurants
Fridge, microwave, oven, stovetop

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

9.8 out of 10, Exceptional, (39)
"Just as in the photos.Well stocked kitchen.Quite small but Thoughtfully laid out and supplied."
Ludlow Village Guest House - prime location on ski shuttle, walk to restaurants
Sutton's Place
Porch

Sutton's Place

2.5 star property
8.0 out of 10, Very good, (45)
"At first we weren’t too sure, as we arrived at night and it felt like walking into a strangers house. However, after we got more comfortable we loved it. No cleanliness issues, very easy to come in and out. Very close to everything you’d want in Manchester and easy parking. "
Sutton's Place
Mountain cabin by skiing with fireplaces & well-equipped kitchen - dog-friendly
Outdoor dining

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.
Terrace/patio

Ski SouthernVermont Getaway.

10.0 out of 10, Exceptional, (63)
"I can’t say enough good things about this lovely home between Rutland and Manchester, VT! The location was ideal for our getaway, surrounded by beautiful hiking trails and the perfect balance of quiet and accessibility. The property itself was charming and cozy, with every detail thoughtfully taken care of – from the fire pit and grill outside to the comfortable indoor setup with board games and TV. The host went above and beyond to make our stay special, even checking in upon our arrival to...
Ski SouthernVermont Getaway.
Inn at Clearwater Pond (Quechee)
Property amenity

Inn at Clearwater Pond (Quechee)

3.5 star property
9.4 out of 10, Exceptional, (44)
"Tina was super accommodating and we had a nice get-away. Super convenient location remote feeling but minutes to all of quechee and very close to woodstock. A local farm recommended and we really enjoyed the rural back roads in this most beautiful part of vermont."
Inn at Clearwater Pond (Quechee)
Renovated guest house. Min from Lake and Skiing.
Fridge, microwave, oven, stovetop

Renovated guest house. Min from Lake and Skiing.

10.0 out of 10, Exceptional, (1)
"A lovely resting spot for my friend and I for two nights. Very clean, quiet, beautiful views from deck and very nice owners."
Renovated guest house. Min from Lake and Skiing.
Cozy, charming cottage 7 mins from Mount Snow and Lake Whitingham
Fridge, microwave, oven, stovetop

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!
Exterior

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

9.6 out of 10, Exceptional, (35)
"Overall good. Very clean, well stocked. Pros: * Bed in master bedroom was comfy * Kitchen was spacious and well stocked (thank you for the coffee and tea options!) * Living room/dining room was spacious and comfortable. Enjoyed the pamphlets left in the box in the dining room with ideas of things to do locally. * Wifi worked well * Loved the Mrs. Meyer's cleaning products (hand soap, dish soap) CONS: * The listing description does not mention that this is a second floor unit - glad my...
1868 CARRIAGE HOUSE-QUAINT + COZY-LESS THAN 20 MIN TO OKEMO!
Magical Retreat Cottage - 15 min to Mt Snow - Ideal workcation
Property grounds

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
Exterior

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"
110 Deluxe Studio Queen on the 1st floor w/ outdoor heated pool
Salt Ash Inn
Billiards

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
Spa reception

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

Log Cabin - Cozy, Quaint & Scenic and Ready for Your Enjoyment!
Interior

Log Cabin - Cozy, Quaint & Scenic and Ready for Your Enjoyment!

9.8 out of 10, Exceptional, (73)
"This cabin was the perfect little spot for a New Years vacation. It’s easy to get to, has parking on site, and is a short drive to get groceries, some shops in town, and more. We loved the nostalgic feel of the appliances and decor, including the retro Nintendo comforter! We cooked all of our meals while here, the stove and oven worked well and there were plenty of pots, pans, etc. The fireplace was easy to use and warmed the entire place well, even during a snowstorm. We made good use to the CD...
Log Cabin - Cozy, Quaint & Scenic and Ready for Your Enjoyment!
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, (21)
"The property is along a well maintained dirt road, which our little EV had no trouble navigating. The cabin stayed very warm, and with no neighbors around it was very peaceful. We had no cell service at the cabin but the wifi worked well, and the hosts provided great communication. Our family had a great time."
Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area
Long Trail House at Stratton Mountain Resort
Condo, 2 Bedrooms | Pool

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 $573
CA $713 total
includes taxes & fees
Mar 3 - Mar 4
Long Trail House at Stratton Mountain Resort
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.