Boutique Hotels & Resorts in Chester from AU$212

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Check availability on Chester Boutique Hotels

Tonight
7 Dec - 8 Dec
Tomorrow
8 Dec - 9 Dec
Next weekend
12 Dec - 14 Dec
In two weeks
19 Dec - 21 Dec

Best Chester Boutique Hotels

No exact matches found, but these alternatives could be just right

Recommended hotels in Chester

Garden
Fullerton Inn

Fullerton Inn

2.5 star property
Chester Depot
8.2 out of 10, Very good, (402)
"Lovely stay"
United States
Christine
The price is AU$212
includes taxes & fees
9 Dec - 10 Dec
Fullerton Inn
Front of property
Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery

3.0 star property
Chester
9.2 out of 10, Wonderful, (107)
"Good breakfast and dinner options. Great location for hiking."
United States
Paul
The price is AU$322
includes taxes & fees
7 Jan - 8 Jan 2026
Stone Hearth Inn and Eatery
Dining
Quaint Queen room at the Chester Inn

Quaint Queen room at the Chester Inn

2.0 star property
Chester Depot
10.0 out of 10, Exceptional, (1)
"This was a wonderful experience for us. The Inn and room were spotless. Very comfortable bed. We will return. The only issue was the tub/shore. Too much of a challenge for older folks. "
United States
Thomas
Quaint Queen room at the Chester Inn
Terrace/patio
Room in Historic Inn! 20 Minutes to Okemo!

Room in Historic Inn! 20 Minutes to Okemo!

Chester Depot
9.2 out of 10, Wonderful, (18)
"The Chester Inn was beautiful and located in downtown Chester. "
United States
Peter C.
The price is AU$293
includes taxes & fees
8 Dec - 9 Dec
Room in Historic Inn! 20 Minutes to Okemo!
Interior
Whimsical Room & Private Bathroom in Historic Inn

Whimsical Room & Private Bathroom in Historic Inn

Chester Depot
8.8 out of 10, Excellent, (9)
"After a long month of work I needed a weekend in VT to calm the nerves. This was a beautiful spot to be in, glad I was here!"
United States
Paul S.
The price is AU$309
includes taxes & fees
8 Dec - 9 Dec
Whimsical Room & Private Bathroom in Historic Inn
Dining
Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!

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

Chester Depot
9.0 out of 10, Wonderful, (2)
"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. "
United States
Jacque
The price is AU$300
includes taxes & fees
8 Dec - 9 Dec
Historic Chester Inn! Circa, 1870 - right on Main Street & 20 minutes to Okemo!
Exterior
Historic 150-year-old farmhouse, Jacuzzi included

Historic 150-year-old farmhouse, Jacuzzi included

Chester Depot
9.8 out of 10, Exceptional, (10)
"This was a lovely inviting piece of history to stay in! The amenities were wonderful, the host very engaged with being sure we had what we needed. It is (for those who may not know Vermont) SUPER close to all sorts of hiking, tours, cute stores and great food! Our family will absolutely stay here again!"
United States
Amy S.
The price is AU$637
includes taxes & fees
9 Dec - 10 Dec
Historic 150-year-old farmhouse, Jacuzzi included
Terrace/patio
Chester Farmhouse Ski Retreat near Slopes

Chester Farmhouse Ski Retreat near Slopes

Chester Depot
9.6 out of 10, Exceptional, (16)
"This was my second time staying at this property. Everything was great just like last year. I highly recommend it if you are staying in Chester, VT. "
United States
Lori N.
The price is AU$510
includes taxes & fees
9 Dec - 10 Dec
Chester Farmhouse Ski Retreat near Slopes
Fridge, microwave, oven, stovetop
Cozy Vermont Cabin · Mountain Views · Near Okemo

Cozy Vermont Cabin · Mountain Views · Near Okemo

Chester
10.0 out of 10, Exceptional, (3)
"We really enjoyed our stay at this home. It had everything we needed and was very comfortable. The countryside around this part of Vermont is beautiful. We found lots of great museums and restaurants. "
United States
Donald M.
The price is AU$1,535
includes taxes & fees
8 Dec - 9 Dec
Cozy Vermont Cabin · Mountain Views · Near Okemo
Interior
King & Queen Suite in Historic Inn Circa 1780

King & Queen Suite in Historic Inn Circa 1780

Chester Depot
9.8 out of 10, Exceptional, (16)
"Central for our needs. easy check in process. Lovely large room with comfy beds. "
United States
HIlary H.
The price is AU$580
includes taxes & fees
3 Jan - 4 Jan 2026
King & Queen Suite in Historic Inn Circa 1780
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.
View all properties

Top Chester Hotel Reviews

On The River Inn

On The River Inn

10/10 Excellent
"Excellent place to stay anytime of the year."
Susan 2-night trip
Posted 3 days ago
On The River Inn
Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

10/10 Excellent
"Staff was great. Our room was okay… broken blinds and lots of scuffs on walls"
Christine 1-night trip
Posted 3 weeks ago
Kimpton Taconic Hotel by IHG

Frequently asked questions

What's there to see and do in Chester?
The shopping, coffee shops and skiing are just some of the things to enjoy while you're in the area. Activities and attractions to experience around Chester include Stratton Mountain Resort, Grafton Historical Society and Weston Playhouse. You might also want to consider exploring Vermont Country Store, Lowell Lake State Park and Magic Mountain Ski Resort while you're here.
What kind of weather should I plan for when I travel to Chester?
Getting an idea of what to expect from the weather in Chester will help you enjoy your stay to the fullest. The hottest months are usually July and August, with an average temperature of 18°C, while the coldest months are January and February, with an average of -4°C. The snowiest months in Chester are January, March, November and February, with each month seeing an average of 35 cm of snowfall.
What's the best way to get to my boutique hotel in Chester?
You have a few options for getting to and around Chester. The closest major airport is Springfield, VT (VSF-Hartness State), which is located 6.6 mi (10.7 km) from the heart of the city, but Rutland, VT (RUT-Rutland Southern Vermont Regional) may also be an option. If you'd like to venture out around the area, you may want to rent a car for your trip.

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