Boutique Hotels & Resorts in Chester from AU$145

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check availability on 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, (410 reviews)
"The room smelled really good but the beds were hard."
United States
Samantha
The price is AU$209
includes taxes & fees
25 Jan - 26 Jan
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, (109 reviews)
"So great all around!"
United States
Janet
The price is AU$423
includes taxes & fees
16 Feb - 17 Feb
Stone Hearth Inn and Eatery
Fridge, microwave, oven, stovetop

Cozy 4bd - Ski Okemo, Killington, Magic & Bromley

Cozy 4bd - Ski Okemo, Killington, Magic & Bromley
Chester
10.0 out of 10, Exceptional, (11 reviews)
"We had a really sweet stay here. It was cozy and comfortable, and had everything as advertised. Plenty of towels and kitchen supplies when we needed them, and the beds were comfortable. We had a great trip to Okemo!"
United States
Carla C.
Cozy 4bd - Ski Okemo, Killington, Magic & Bromley
Exterior

Historic 150-year-old farmhouse, Jacuzzi included

Historic 150-year-old farmhouse, Jacuzzi included
Chester Depot
9.8 out of 10, Exceptional, (13 reviews)
"Brought my mom here for leaf peeping. The Farmhouse was clean, comfortable and very inviting. Plenty to do in the surrounding area. Soaking in the hot tub & stargazing in the evening was wonderful! Owner was easy to communicate with. Would highly recommend!"
United States
Michele B.
The price is AU$774
includes taxes & fees
27 Jan - 28 Jan
Historic 150-year-old farmhouse, Jacuzzi included
Dining

Chester Farmhouse Ski Retreat near Slopes

Chester Farmhouse Ski Retreat near Slopes
Chester Depot
9.6 out of 10, Exceptional, (18 reviews)
"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$538
includes taxes & fees
28 Jan - 29 Jan
Chester Farmhouse Ski Retreat near Slopes
Exterior

Cozy Vermont Cabin · Mountain Views · Near Okemo

Cozy Vermont Cabin · Mountain Views · Near Okemo
Chester
10.0 out of 10, Exceptional, (3 reviews)
"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$1,647
includes taxes & fees
4 Feb - 5 Feb
Cozy Vermont Cabin · Mountain Views · Near Okemo
Breakfast area

The Covered Bridge Inn

The Covered Bridge Inn
2.5 star property
Brattleboro
7.6 out of 10, Good, (1,000 reviews)
"Easy check in and good parking"
United States
nicholas
The price is AU$145
includes taxes & fees
8 Feb - 9 Feb
The Covered Bridge Inn
Porch

The Manchester View

The Manchester View
2.5 star property
Manchester Center
9.4 out of 10, Exceptional, (802 reviews)
"Great staff, huge clean room, tasty continental breakfast."
United States
Carey
The Manchester View
Exterior

Best Western Springfield Hotel

Best Western Springfield Hotel
2.5 star property
Springfield
8.8 out of 10, Excellent, (814 reviews)
"Staff was so nice!! "
United States
Stephanie
The price is AU$249
includes taxes & fees
28 Jan - 29 Jan
Best Western Springfield Hotel
Lobby

Comfort Inn & Suites Brattleboro I-91

Comfort Inn & Suites Brattleboro I-91
2.5 star property
Brattleboro
8.6 out of 10, Excellent, (758 reviews)
"The room was clean and the staff was wonderful"
United States
Julianne
The price is AU$218
includes taxes & fees
29 Jan - 30 Jan
Comfort Inn & Suites Brattleboro I-91
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
"Our stay was absolutely wonderful. The room was clean & comfortable with a nice view from balcony. The breakfast was good & the bar was very nice on a cold evening. Look forward to staying here again."
Chris 2-night trip
Posted 10 days ago
On The River Inn
Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

10/10 Excellent
"Staff, cleanliness, ambience, restaurant, all perfect! We can’t wait to return! "
Heather 1-night trip
Posted 2 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 Okemo Mountain Resort, Stratton Mountain Resort and Weston Playhouse. You might also want to consider exploring DaVallia Art & Accents, Bonnie's Bundles Dolls and Vermont Country Store 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.

Explore a world of travel with Expedia