Chester hotels

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Best Chester hotels

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$167 - $170$170 - $173$173 - $176$176 - $179$179+ per night

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Most recommended Chester hotels

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Motel In The Meadow - Chester - Bedroom
Motel In The Meadow
Chester, VT
10Wonderful(1)
Free Wi-Fi
Pet friendly
$86+
Check availability
Hugging Bear Inn and Shoppe - Chester
Hugging Bear Inn and Shoppe
Chester, VT
9.1Wonderful(158)
$167+
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The Fullerton Inn - Chester - Bedroom
The Fullerton Inn
Chester, VT
7.4Good(355)
Free Wi-Fi
$173+
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Rose Arbour Bed and Breakfast - Chester
Rose Arbour Bed and Breakfast
Chester, VT
5.1Fair(1)
Free Wi-Fi
$179+
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Chester Inn - Chester
Chester Inn
Chester, VT
8.4Very good(186)
Parking
Free Wi-Fi
$185+
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Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area - Chester - Restaurant
Luxury Glamping Cabin. Close to hiking and 15 minutes from Ski Area
Chester, VT
Free Wi-Fi
$192+
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Whimsical Room & Private Bathroom in Historic Inn - Chester - Living room
Whimsical Room & Private Bathroom in Historic Inn
Chester, VT
Free Wi-Fi
$216+
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The Karass Inn - Chester
The Karass Inn
Chester, VT
8.8Very good(162)
Free Wi-Fi
$249+
Check availability
Log Cabin - Cozy, Quaint & Scenic and ready for Your Enjoyment! - Chester - Living room
Log Cabin - Cozy, Quaint & Scenic and ready for Your Enjoyment!
Chester, VT
Pool
$332+
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Cozy 4bd - Ski Okemo, Killington, Magic & Bromley - Chester - Dining room
Cozy 4bd - Ski Okemo, Killington, Magic & Bromley
Chester, VT
Free Wi-Fi
$332+
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Stone Hearth Inn and Eatery - Chester - Living room
Stone Hearth Inn and Eatery
Chester, VT
9.1Wonderful(135)
Parking
Free Wi-Fi
$403+
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Country Riverside Retreat - Chester
Country Riverside Retreat
Chester, VT
$413+
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Spacious 1-level ranch, mtn. views, htd. flrs , fire pit, 10 mi. to Okemo! - Chester
Spacious 1-level ranch, mtn. views, htd. flrs , fire pit, 10 mi. to Okemo!
Chester, VT
$532+
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Indoor Hot Tub Room/10 Miles to Okemo - Chester - Living room
Indoor Hot Tub Room/10 Miles to Okemo
Chester, VT
Free Wi-Fi
$615+
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Inn Victoria - Chester
Inn Victoria
Chester, VT
9.6Wonderful(82)
Parking
Free Wi-Fi
$654+
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Gorgeous Log Home With Mountain Views with Hot Tub - Chester
Gorgeous Log Home With Mountain Views with Hot Tub
Chester, VT
9.7Wonderful(26)
Free Wi-Fi
Spa
$1,088+
Check availability
Useful Info

KAYAK’s insights for hotels in Chester

Discover seasonal trends, ideal booking windows, and other data-driven tips to plan your stay in Chester with confidence.

Which month has the cheapest hotel rates in Chester?

Hotels are cheapest in Chester in June, with average rates of $136. In comparison, January is the most expensive month, with prices at $418.

What is the cheapest day of the week to book a hotel in Chester?

Tuesday offers the lowest rates in Chester, with an average nightly price of $127. The highest prices are found on Thursday, with average rates at $237.
Find deals

KAYAK's top tips for finding Chester hotel deals

  • How long should you stay? KAYAK users usually book their hotel in Rutland for 1 day.

FAQs when booking a hotel in Chester

  • Which freebies do KAYAK users look for when booking a hotel in Chester?

    KAYAK users look for a hotel in Chester with free breakfast.

  • How do I find a hotel in central Chester?

    After you launch a hotel search on KAYAK, you can refine your research by neighborhood, which allows you to pick the central Chester districts. You can also do a search using the city map to choose a specific location, like Chester city center.

  • How can I find hotels near me?

    Take a look at our extensive hotel map to find the best hotels near you.

Where to stay in Chester?

Our map will help you find the perfect place to stay in Chester by showing you the exact location of each hotel.

Everything you need to know for your stay in Chester

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