Hotels in Chester
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Aug 24 - Aug 25Tomorrow
Aug 25 - Aug 26This weekend
Aug 28 - Aug 30Next weekend
Sep 4 - Sep 6Top 5 hotels in Chester at a glance
- Pointe at Castle Hill Resort — 3.5-star hotel in Cavendish. Guest rating: 8.8/10 — Excellent.
- Stone Hearth Inn and Eatery — 3-star hotel in Chester. Guest rating: 9.2/10 — Wonderful.
- Killington Mountain Lodge, Tapestry Collection by Hilton — 3.5-star hotel in Killington. Guest rating: 7.4/10 — Good.
- Best Western Springfield Hotel — 2.5-star hotel in Springfield. Guest rating: 8.8/10 — Excellent.
- The Inn at Weathersfield — 4-star hotel in Perkinsville. Guest rating: 9.8/10 — Exceptional.
Where to stay in Chester?
Pointe at Castle Hill Resort
Pointe at Castle Hill ResortCavendish
$152
$173 total
includes taxes & fees
Aug 25 - Aug 26
Stone Hearth Inn and Eatery
Stone Hearth Inn and EateryChester
$209
$228 total
includes taxes & fees
Aug 25 - Aug 26
Killington Mountain Lodge, Tapestry Collection by Hilton
Killington Mountain Lodge, Tapestry Collection by HiltonKillington
$155
$171 total
includes taxes & fees
Aug 30 - Aug 31
Best Western Springfield Hotel
Best Western Springfield HotelSpringfield
$161
$177 total
includes taxes & fees
Aug 31 - Sep 1
The Inn at Weathersfield
The Inn at WeathersfieldPerkinsville
$219
$275 total
includes taxes & fees
Aug 25 - Aug 26
Fullerton Inn
Fullerton InnChester Depot
$139
$152 total
includes taxes & fees
Aug 31 - Sep 1
Align Inn Vermont
Align Inn VermontQuechee
$119
$131 total
includes taxes & fees
Aug 25 - Aug 26
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
Holiday Inn Club Vacations Mount Ascutney Resort by IHGBrownsville
$139
$168 total
includes taxes & fees
Aug 25 - Aug 26
Fireside Inn & Suites West Lebanon
Fireside Inn & Suites West LebanonWest Lebanon
$162
$176 total
includes taxes & fees
Sep 6 - Sep 7
Jackson Gore Village, A Vail Resorts Property
Jackson Gore Village, A Vail Resorts PropertyJackson Gore Base Area
$185
$224 total
includes taxes & fees
Sep 22 - Sep 23
Woodstock Inn & Resort
Woodstock Inn & ResortWoodstock
$409
$494 total
includes taxes & fees
Sep 7 - Sep 8
Castle Hill Resort And Spa
Castle Hill Resort And SpaCavendish
$269
$293 total
includes taxes & fees
Aug 27 - Aug 28
The Mountain Inn at Killington
The Mountain Inn at KillingtonKillington
$139
$161 total
includes taxes & fees
Aug 25 - Aug 26
The Upper Pass Lodge at Magic Mountain
The Upper Pass Lodge at Magic MountainLondonderry
$93
$103 total
includes taxes & fees
Sep 22 - Sep 23
Go beyond your typical stay in Chester
Pet friendly
Apartment
Condo
Cottage
Family friendly
Our prices for hotels in Chester are cheapest in December
Our prices for hotels in Chester are cheapest in December
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 and Suites Manchester
10/10 Excellent
"Great place! A little expensive"
On The River Inn
8/10 Good
"Everything about the Inn was great. There was a major price discrepancy between the 3rd party booking site I used (Expedia) and what was actually charged but I have yet to get to the bottom of the issue."
Keene Elm City Hotel, an Ascend Collection Hotel
8/10 Good
"The room was clean and stocked with the amenities expected, including a fridge and a microwave. Staff was very helpful and kind on check in. Breakfast was a standard continental. Not the best food but there was an array of options."
Colonial Motel
8/10 Good
"X"
Claremont Motor Lodge
8/10 Good
"Sorry. I do not wish to write a review."
The Shire Woodstock
10/10 Excellent
"Great stay, staff and room was great. Bed was super comfy. Only flaw, they should put a fence up in front of garbage and dumpsters. They are an eye sore."
Holiday Inn Club Vacations Mount Ascutney Resort by IHG
8/10 Good
"The place was clean and well maintained. Ample room and comfortable as well. Having a kitchen and having it properly equipped was a big plus."
Latchis Hotel
8/10 Good
"The art deco building is gorgeous. I applaud the non-profit organization that saved, renovated and maintains this exceptional building. I very much appreciated the original bathroom fixtures. The hotel really gives you a taste of what it might have been like to travel back in the 1930-40s. On the downside, my experience was not the best: When I arrived, the front desk lady said something like: "I'll be right with you". Two minutes later, she came to the front desk joking about having problems with her Emails. Not acceptable! You should pause your Email activity when someone is waiting in the lobby. My wife and I were looking forward to a drink at the hotel bar. The website indicated that the bar was open, and a note on the door confirmed. There was nobody there. Money and a lady's purse were spread out on the bar. We were told at the front desk that the people running the bar for them decided not to open that evening. Not acceptable. The next morning I took a lukewarm shower, as it took about ten minutes for the water to become warm enough, By then I was done and my feet were in about 5" of dirty water because the drain was clogged. We were also told that if we did not turn in our brass key, they would charge us $75 to replace it. When walked down to the lobby, there was a sign stating that front desk duty started at 9:00."
Hampton Inn Brattleboro
10/10 Excellent
"Staff were extremely friendly. The whole place was clean. Hit tub was really a whirlpool..movement but no bubbles. So nice and warm though. Great stay!!"