Properties are selected based on real traveler reviews and popularity among guests who’ve booked a night in Chester on Hotels.com. These Chester hotels consistently deliver on comfort, location and traveler experience. Last updated on .
Hotels in Chester
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Aug 30 - Aug 31Tomorrow
Aug 31 - Sep 1Next weekend
Sep 4 - Sep 6In two weeks
Sep 11 - Sep 13Where to stay in Chester?
Fullerton Inn
Fullerton InnChester Depot
CNY935
CNY1,020 total
includes taxes & fees
Sep 1 - Sep 2
Stone Hearth Inn and Eatery
Stone Hearth Inn and EateryChester
CNY1,406
CNY1,532 total
includes taxes & fees
Aug 31 - Sep 1
Best Western Springfield Hotel
Best Western Springfield HotelSpringfield
CNY1,204
CNY1,325 total
includes taxes & fees
Sep 1 - Sep 2
The Hartness House
The Hartness HouseSpringfield
CNY1,193
CNY1,312 total
includes taxes & fees
Aug 31 - Sep 1
Harvest Barn Inn
Harvest Barn InnBellows Falls
CNY1,170
CNY1,275 total
includes taxes & fees
Aug 31 - Sep 1
Pointe at Castle Hill Resort
Pointe at Castle Hill ResortCavendish
CNY781
CNY891 total
includes taxes & fees
Aug 31 - Sep 1
Castle Hill Resort And Spa
Castle Hill Resort And SpaCavendish
CNY1,811
CNY1,974 total
includes taxes & fees
Aug 31 - Sep 1
The Common Man Inn & Restaurant
The Common Man Inn & RestaurantClaremont
CNY902
CNY979 total
includes taxes & fees
Sep 7 - Sep 8
Blue Gentian Lodge at Magic Mountain
Blue Gentian Lodge at Magic MountainLondonderry
CNY1,003
CNY1,103 total
includes taxes & fees
Aug 31 - Sep 1
Jackson Gore Village, A Vail Resorts Property
Jackson Gore Village, A Vail Resorts PropertyJackson Gore Base Area
CNY1,112
CNY1,351 total
includes taxes & fees
Sep 30 - Oct 1
The Upper Pass Lodge at Magic Mountain
The Upper Pass Lodge at Magic MountainLondonderry
CNY616
CNY684 total
includes taxes & fees
Sep 3 - Sep 4
Main and Mountain Bar & Motel
Main and Mountain Bar & MotelLudlow
CNY1,143
CNY1,257 total
includes taxes & fees
Sep 6 - Sep 7
The Inn at Weathersfield
The Inn at WeathersfieldPerkinsville
CNY1,192
CNY1,547 total
includes taxes & fees
Sep 2 - Sep 3
Claremont Motor Lodge
Claremont Motor LodgeClaremont
CNY740
CNY803 total
includes taxes & fees
Aug 31 - Sep 1
Holiday Inn Express Hotel & Suites Brattleboro by IHG
Holiday Inn Express Hotel & Suites Brattleboro by IHGBrattleboro
CNY1,137
CNY1,251 total
includes taxes & fees
Sep 13 - Sep 14
The Putney Inn
The Putney InnPutney
CNY733
CNY806 total
includes taxes & fees
Aug 31 - Sep 1
Bromley View Inn
Bromley View InnBondville
CNY515
CNY566 total
includes taxes & fees
Aug 31 - Sep 1
Hampton Inn and Suites Manchester
Hampton Inn and Suites ManchesterManchester Center
CNY1,043
CNY1,147 total
includes taxes & fees
Sep 8 - Sep 9
Sun Lodge near Manchester VT, Ascend Collection Hotel
Sun Lodge near Manchester VT, Ascend Collection HotelBromley Mountain
CNY909
CNY1,000 total
includes taxes & fees
Sep 6 - Sep 7
Go beyond your typical stay in Chester
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Our prices for hotels in Chester are cheapest in May
Our prices for hotels in Chester are cheapest in May
Price trends for hotels in Chester
Pricing is based on two traveler single night rates
Top neighborhoods in Chester
Chester Depot
The Chester Depot neighborhood has lots to see including DaVallia Art & Accents and Bonnie's Bundles Dolls.
Top landmarks in Chester
Bonnie's Bundles Dolls
7.6/10 (4 reviews)
Chester Depot is home to Bonnie's Bundles Dolls, so why not stop by during your stay in Chester. If you have fun at Bonnie's Bundles Dolls, you'll love DaVallia Art & Accents, located nearby.
DaVallia Art & Accents
10.0/10 (2 reviews)
Chester Depot is home to DaVallia Art & Accents, so why not stop by during your stay in Chester. If you have fun at DaVallia Art & Accents, you'll love Bonnie's Bundles Dolls, located nearby.
Learn more about Chester
Notable for its skiing, Chester features attractions such as DaVallia Art & Accents and Bonnie's Bundles Dolls. Visitors speak highly of this relaxing city's coffeehouses and small-town setting.
See all hotels in Chester
Check out reviews of Chester hotels guests love
Hampton Inn Brattleboro
10/10 Excellent
"I really have no complaints whatsoever! I would’ve loved a pancake conveyor belt to go with the breakfast but the waffle irons did the trick just the same."
Claremont Motor Lodge
8/10 Good
"Staff was nice and friendly"
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
10/10 Excellent
"There was a lot to love about Holiday Inn Club Vacations Mount Ascutney, especially for a larger family or group. Our three-bedroom villa was BY FAR the largest accommodation of our trip and surprisingly affordable. We had tons of room to spread out, a decent-sized kitchen for cooking, and FREE laundry—a huge win during a long road trip! The villa kitchen was helpful but pretty minimally stocked. Cooking utensils and cutting boards were lacking, so bring some basics if you plan to cook. Grills are available, but you’ll need charcoal. I’d recommend buying it and any groceries before arriving because the onsite marketplace is expensive. The biggest disappointment was the pool, which is closed through 2027. Traveling with kids, that was a major bummer and definitely something families should know before booking. The location is incredibly beautiful, tucked away on a Vermont mountainside, but it is truly in the middle of nowhere. Come prepared! Overall, the incredible amount of space and affordability made it work really well for our group. It wasn’t our favorite stay of the trip, but the value for a three-bedroom villa was hard to beat."
Keene Elm City Hotel, an Ascend Collection Hotel
10/10 Excellent
"Room was clean and staff was excellent. Breakfast was good and plentiful."
The Palmer House Resort, an Ascend Collection Hotel
10/10 Excellent
"Nice room and property. With was down."
The Equinox Golf Resort And Spa
10/10 Excellent
"First time stay here since we used to own a house in the area. Found the Inn comfortable and the amenities are amazing."
On The River Inn
10/10 Excellent
"This was one of the nicest hotels I have ever stayed in! We had a river view room with rocking chairs on the balcony, s’mores kits were offered every night (pick up by the front desk) and 2 fire pits to choose from. Game room was cute (although the air hockey table’s fan wasn’t strong on one side), library was absolutely gorgeous. Loved having water refilling stations on 2 of the 3 floors and 24/7 coffee/tea stations, too. Queen beds were very comfy, and the room was so spacious. I’d love another piece of furniture with drawers to keep our stuff though - we lived out of our suitcases because there was only an armoire with 3 half drawers. And maybe another towel bar or hooks in the bathroom to hang the towels to dry, especially if you have 4 people in a room. Breakfast buffet (included with our Expedia stay but extra for others) was always hot & fresh. We had 4 breakfasts: French toast, pancakes, waffles, french toast again. There was always fresh homemade pastries and muffins, yogurt, and oatmeal. I would have loved some fresh fruit like berries to go with the yogurt instead of apples and oranges. Staff was always so nice and helpful, especially at breakfast. Housekeeping forgot twice to give us the 4 fresh towels (gave 3 instead) but we got replacements when we asked at the desk."
Bromley View Inn
10/10 Excellent
"Beautiful cozy inn surrounded by trees and mountains. An incredible view with a cabin setting. Check-in was simple with coffee available 24/7"
The Shire Woodstock
8/10 Good
"We enjoyed our stay very much. We found our stay to very quiet. The back of the property was so peaceful and relaxing sitting by the river, listening to the birds and the gurgling of the river as it moves along. The room was comfortable with a fridge and freezer for snacks/fruit etc. I'd like to see another chair in the room so that 2 people can sit by the window and experience the view although this wasn't a game changer."
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