Chester hotels

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Best Chester hotels

Discover the best hotels in Chester and compare prices, ratings, and locations to find the right stay for your trip.
These are the best prices for May 2 - 3.
Chester Inn - Chester - Living room

Chester Inn

Chester, VT

8.4

$118+

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Fullerton Inn - Chester - Bedroom

Fullerton Inn

Chester, VT

7.4

$147+

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Stone Hearth Inn and Eatery - Chester - Living room

Stone Hearth Inn and Eatery

Chester, VT

8.8

$229+

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Chester Farmhouse on 100 Acres, 15 Min to Okemo! - Chester - Bedroom

Chester Farmhouse on 100 Acres, 15 Min to Okemo!

Chester, VT

10.0

$361+

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Peaceful Brookside Getaway about 10 Mi to Okemo Slopes! - Chester - Living room

Peaceful Brookside Getaway about 10 Mi to Okemo Slopes!

Chester, VT

9.7

$238+

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King & Queen Suite in Historic Inn Circa 1780 - Chester - Living room

King & Queen Suite in Historic Inn Circa 1780

Chester, VT

9.4

$202+

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Charming Chester Farmhouse near Near VT Slopes - Chester - Dining room

Charming Chester Farmhouse near Near VT Slopes

Chester, VT

9.5

$411+

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Honeymoon Suite with Jacuzzi Tub in Historic Inn - Chester - Living room

Honeymoon Suite with Jacuzzi Tub in Historic Inn

Chester, VT

8.8

$239+

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Vermont Charm in the 1840 Gideon Lee House - Chester - Living room

Vermont Charm in the 1840 Gideon Lee House

Chester, VT

10.0

$340+

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Historic 150-year-old farmhouse, Jacuzzi included - Chester - Building

Historic 150-year-old farmhouse, Jacuzzi included

Chester, VT

9.6

$444+

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Top-rated hotels

Stay at the hotels that our users loved the most May 2 - 3.
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Vermont Charm in the 1840 Gideon Lee House - Chester - Living room

Vermont Charm in the 1840 Gideon Lee House

Chester, VT

10.0

$340+

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Log Cabin Retreat - Chester, Vt 25 Acres + State Forest Access - Chester - Living room

Log Cabin Retreat - Chester, Vt 25 Acres + State Forest Access

Chester, VT

10.0

$460+

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Chester Farmhouse on 100 Acres, 15 Min to Okemo! - Chester - Bedroom

Chester Farmhouse on 100 Acres, 15 Min to Okemo!

Chester, VT

10.0

$361+

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Vacation Rental - Choose from 5 nearby mountains or relax in peace & comfort - Chester - Balcony

Vacation Rental - Choose from 5 nearby mountains or relax in peace & comfort

Chester, VT

10.0

$534+

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Cozy 4bd - Ski Okemo, Killington, Magic & Bromley - Chester - Dining room

Cozy 4bd - Ski Okemo, Killington, Magic & Bromley

Chester, VT

10.0

$391+

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Hotel deals for next week

Some of KAYAK users’ favorite hotels with availability next week May 2 - 3.
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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

9.8

$180+

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The Cairn, 1840s Cozy Stone Cottage, Pet Friendly - Chester - Patio

The Cairn, 1840s Cozy Stone Cottage, Pet Friendly

Chester, VT

9.8

$266+

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The Spruce Guesthouse: A Beautifully Renovated Contemporary Barn. - Chester - Dining room

The Spruce Guesthouse: A Beautifully Renovated Contemporary Barn.

Chester, VT

9.9

$594+

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'Everything Vt' Getaway Centrally Located: Ski, Shop, Golf, Hike, Relax - Chester - Living room

'Everything Vt' Getaway Centrally Located: Ski, Shop, Golf, Hike, Relax

Chester, VT

10.0

$472+

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Whimsical Room & Private Bathroom in Historic Inn - Chester - Living room

Whimsical Room & Private Bathroom in Historic Inn

Chester, VT

8.7

$192+

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Work, Ski, Relax - Big Restored 1860s Farmhouse - Chester - Living room

Work, Ski, Relax - Big Restored 1860s Farmhouse

Chester, VT

10.0

$1,296+

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Cheap hotels in Chester

Find deals on some of our best-value hotels May 2 - 3.
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Vermont Hillside Cottage w/Great View - Pet Friendly, Fee Required - Chester - Balcony

Vermont Hillside Cottage w/Great View - Pet Friendly, Fee Required

Chester, VT

9.8

$144+

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Sage House at Camp Greenwood Vermont with Sauna - Chester - Living room

Sage House at Camp Greenwood Vermont with Sauna

Chester, VT

9.8

$249+

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| Handmade 4 Bed Log Cabin | 5 Min From Skiing | - Chester

| Handmade 4 Bed Log Cabin | 5 Min From Skiing |

Chester, VT

9.2

$265+

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Hike, Ski and Unwind Cabin with Deck in Chester! - Chester

Hike, Ski and Unwind Cabin with Deck in Chester!

Chester, VT

6.0

$266+

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Cheerful residential home with lots of space - Chester - Living room

Cheerful residential home with lots of space

Chester, VT

9.9

$292+

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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

9.7

$332+

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Popular filters in Chester hotels

Hotels with free cancellation
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Good to know

Low season

High season

Average price (weeknight)

Average price (weekend night)

January
November
$295
$263
Cheapest month to stay with an average 9% drop in price.
Most expensive month to stay with an average 2% rise in price.
Average Sun - Thu price over the last 2 weeks.
Average Fri & Sat price over the last 2 weeks.

KAYAK's top tips for finding Chester hotel deals

  • If you’re looking for a cheap hotel in Rutland, you should consider visiting during the low season. You'll find cheaper hotels in Rutland in January and November.
  • Hotel room prices vary depending on many factors but you’ll most likely find the best hotel deals in Rutland if you stay on a Friday. The opposite is true for, Sunday, which is usually the most expensive day.
  • 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