aerial view of the Quechee Covered Bridge, over the Ottauquechee River, Quechee Vermont

Boutique Hotels & Resorts in Chester from AU$152

  • 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, (437 reviews)
"Beautiful old inn Great Staff"
United States
Elizabeth A
The price is AU$215
includes taxes & fees
17 June - 18 June
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, (119 reviews)
"Friendly helpful clean. Bathroom clean. Nice pillows. A/c was super because it was very hot outside. Breakfast was very good"
United States
Kathleen
The price is AU$291
includes taxes & fees
17 June - 18 June
Stone Hearth Inn and Eatery
Exterior

Historic 150-year-old farmhouse, Jacuzzi included

Historic 150-year-old farmhouse, Jacuzzi included
Chester Depot
9.8 out of 10, Exceptional, (17 reviews)
"Our Stay was outstanding. 20 minutes from Okemo! Hot Tub was excellent; the beds were super comfortable, and Colin's food recommendations were spot on. I will be coming to this house again next year!"
United States
Kevin K.
The price is AU$648
includes taxes & fees
17 June - 18 June
Historic 150-year-old farmhouse, Jacuzzi included
Exterior

Tranquil 3 bedroom Home with Hot Tub and Standby Generator in Andover

Tranquil 3 bedroom Home with Hot Tub and Standby Generator in Andover
Andover
The price is AU$819
includes taxes & fees
17 June - 18 June
Tranquil 3 bedroom Home with Hot Tub and Standby Generator in Andover
Dining

Charming Chester Farmhouse near Near VT Slopes

Charming Chester Farmhouse near Near VT Slopes
Chester Depot
9.4 out of 10, Exceptional, (22 reviews)
"We had a great stay! The house was clean, comfortable, and exactly as described. The location was perfect and the host was very responsive. We’d definitely stay here again and highly recommend it."
United States
Stephanie F.
The price is AU$574
includes taxes & fees
17 June - 18 June
Charming Chester Farmhouse near Near VT Slopes
Exterior

Cozy Vermont Cabin · Mountain Views · Near Okemo

Cozy Vermont Cabin · Mountain Views · Near Okemo
Chester
10.0 out of 10, Exceptional, (4 reviews)
"Clean, spacous house, good location and great scenes of the mountains."
United States
pauline
The price is AU$1,397
includes taxes & fees
29 June - 30 June
Cozy Vermont Cabin · Mountain Views · Near Okemo
Lobby

Keene Elm City Hotel, an Ascend Collection Hotel

Keene Elm City Hotel, an Ascend Collection Hotel
2.5 star property
Keene
8.6 out of 10, Excellent, (1,004 reviews)
"Good stay everything you could ask for from a budget friendly hotel."
United States
Stephen
The price is AU$167
includes taxes & fees
18 June - 19 June
Keene Elm City Hotel, an Ascend Collection Hotel
Exterior

Best Western Springfield Hotel

Best Western Springfield Hotel
2.5 star property
Springfield
8.8 out of 10, Excellent, (862 reviews)
"Great place to stay"
United States
Daniel
The price is AU$265
includes taxes & fees
24 June - 25 June
Best Western Springfield Hotel
Signature Suite, Kitchen, Mountain View | Living area

Brittany Motel

Brittany Motel
2.0 star property
Manchester Center
9.4 out of 10, Exceptional, (365 reviews)
"The bed was very comfortable! We had a great sleep and made our breakfast in the "snack room". It was pleasant and quiet- we sat on chairs out front looking at the mountain in front of us. It was a great place to stay."
United States
Susan
The price is AU$152
includes taxes & fees
17 June - 18 June
Brittany Motel
Restaurant

Best Western Plus Keene Hotel

Best Western Plus Keene Hotel
3.0 star property
Keene
8.4 out of 10, Very good, (1,005 reviews)
"Best place to stay the food was good and we had a wonderful stay. Swimming pool was fun and safe for kids"
United States
Nidia Ruby
The price is AU$183
includes taxes & fees
21 June - 22 June
Best Western Plus Keene Hotel
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

Latchis Hotel

Latchis Hotel

10/10 Excellent
"This was my second stay at The Latchis, and once again it was a great experience. The hotel is clean, the staff are consistently friendly and welcoming, and the location is incredibly convenient—especially for those of us coming up from New York on Amtrak. One of my favorite things about staying here is the building itself. The Latchis has so much character and history, and it's a refreshing change from a typical chain hotel. It adds something special to the whole experience. I'll definitely be back on my next trip to Brattleboro!"
Kaitlin 3-night trip
Posted 5 hours ago
Latchis Hotel

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 DaVallia Art & Accents, Weston Playhouse and Bellows Falls Opera House. You might also want to consider exploring Bonnie's Bundles Dolls, Vermont Country Store and Lowell Lake State Park 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