A covered wooden bridge over a river, surrounded by rocky terrain and greenery.

Boutique Hotels & Resorts in Chester

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Check availability on Chester Boutique Hotels

Tonight
10 Aug - 11 Aug
Tomorrow
11 Aug - 12 Aug
This weekend
14 Aug - 16 Aug
Next weekend
21 Aug - 23 Aug
No exact matches found, but these alternatives could be just right

Recommended hotels in Chester

1. Fullerton Inn

Fullerton Inn
Chester Depot
United States
Kirsty
AU$214
includes taxes & fees
31 Aug - 1 Sept
Fullerton Inn

2. Stone Hearth Inn and Eatery

Stone Hearth Inn and Eatery
Chester
United States
Kathleen
AU$322
includes taxes & fees
12 Aug - 13 Aug
Stone Hearth Inn and Eatery

3. Charming Chester Farmhouse near Near VT Slopes

Charming Chester Farmhouse near Near VT Slopes
Chester Depot
United States
Stephanie F.
AU$588
includes taxes & fees
11 Aug - 12 Aug
Charming Chester Farmhouse near Near VT Slopes

4. Historic 150-year-old farmhouse, Jacuzzi included

Historic 150-year-old farmhouse, Jacuzzi included
Chester Depot
United States
Ryan K.
AU$663
includes taxes & fees
8 Sept - 9 Sept
Historic 150-year-old farmhouse, Jacuzzi included

5. Cozy Vermont Cabin · Mountain Views · Near Okemo

Cozy Vermont Cabin · Mountain Views · Near Okemo
Chester
United States
pauline
AU$1,406
includes taxes & fees
17 Aug - 18 Aug
Cozy Vermont Cabin · Mountain Views · Near Okemo

6. Tranquil 3 bedroom Home with Hot Tub/Fast WIFI/Standby Generator in Andover

Tranquil 3 bedroom Home with Hot Tub/Fast WIFI/Standby Generator in Andover
Andover
United States
Lorraine C.
AU$885
includes taxes & fees
17 Aug - 18 Aug
Tranquil 3 bedroom Home with Hot Tub/Fast WIFI/Standby Generator in Andover

7. Best Western Springfield Hotel

Best Western Springfield Hotel
Springfield
United States
Gerry
AU$279
includes taxes & fees
17 Aug - 18 Aug
Best Western Springfield Hotel

8. The Landgrove

The Landgrove
Londonderry
United States
Jared
AU$322
includes taxes & fees
3 Sept - 4 Sept
The Landgrove

9. Harvest Barn Inn

Harvest Barn Inn
Bellows Falls
Canada
Natalie
AU$252
includes taxes & fees
17 Aug - 18 Aug
Harvest Barn Inn

10. The Hartness House

The Hartness House
Springfield
United States
Dan
AU$299
includes taxes & fees
20 Aug - 21 Aug
The Hartness House
View all properties

Top Chester Hotel Reviews

Latchis Hotel

Latchis Hotel

8/10 Good
"In an old Theater building. Definitely has character and cool features. We arrived too late for the movies, but still fun. In central Brattleboro which has some interesting shops, but is suffering from homelessnes and mental illness/drug use. Didnt really feel unsafe and we walked a few blocks to a fun restaurant with good food & karioke. Person at desk was lovely and helpful. Room was ok- a little dated and could be cleaner."
Jonathan 1-night trip
Posted 15 hours ago
Latchis Hotel
Kimpton Taconic Hotel by IHG

Kimpton Taconic Hotel by IHG

10/10 Excellent
"Excellent amenities and perfect if you're traveling with a dog to VT. Rooms are very nice albeit a bit small and very low water pressure in the shower."
Yvette 1-night trip
Posted 7 days 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 DaVallia Art & Accents, Weston Playhouse and Grafton Valley Arts Guild Cricketers Gallery. 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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