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Chester vacation rentals

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Best Chester vacation rentals

Most recommended vacation rentals in Chester

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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
$157+
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Charming Farmhouse in Chester - Chester - Living room
Charming Farmhouse in Chester
Chester, VT
$424+
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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
Pool
$332+
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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
$760+
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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
$197+
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Zen Of The Woods Tiny Cabin In Okemo Val - Chester - Bedroom
Zen Of The Woods Tiny Cabin In Okemo Val
Chester, VT
9.5Wonderful(6)
$288+
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Log cabin near Okemo / Ludlow on 25 acres borders state forest w/trails nearby - Chester - Living room
Log cabin near Okemo / Ludlow on 25 acres borders state forest w/trails nearby
Chester, VT
Free Wi-Fi
$523+
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WhiSki Cabin 12-acres with mountain views! - Chester - Dining room
WhiSki Cabin 12-acres with mountain views!
Chester, VT
Parking
Free Wi-Fi
$823+
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Cheerful residential home with lots of space - Chester - Living room
Cheerful residential home with lots of space
Chester, VT
Free Wi-Fi
$342+
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Vermont Hillside Cottage w/Great View - Pet Friendly - Chester
Vermont Hillside Cottage w/Great View - Pet Friendly
Chester, VT
Pet friendly
$159+
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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+
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Historic Vermont Village Home & Guest Suite - Hike, Bike, & Relax - Chester
Historic Vermont Village Home & Guest Suite - Hike, Bike, & Relax
Chester, VT
Pool
$198+
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Beautifully Renovated 1850’s Victorian Home In The Village Of Chester - Chester
Beautifully Renovated 1850’s Victorian Home In The Village Of Chester
Chester, VT
$362+
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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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Peaceful Brookside Getaway about 10 Mi to Okemo Slopes! - Chester
Peaceful Brookside Getaway about 10 Mi to Okemo Slopes!
Chester, VT
10Wonderful(1)
Free Wi-Fi
Pet friendly
$245+
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Log cabin in the Smokeshire Valley area of Chester. - Chester
Log cabin in the Smokeshire Valley area of Chester.
Chester, VT
Free Wi-Fi
Pet friendly
$321+
Check availability
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Good to know

Low season

April

High season

December

Average price (weeknight)

$358

Average price (weekend night)

$549
Cheapest month to stay with an average 60% drop in price.
Most expensive month to stay with an average 21% 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 vacation rental deals

  • The best vacation rental properties in Chester are Chester Home w/ Views ~ 10 Mi to Okemo Mtn Resort! (10.0, 25 reviews), Vermont Hillside Cottage w/Great View - Pet Friendly (9.9, 20), and The Spruce Guesthouse: A Beautifully Renovated Contemporary Barn. (9.9, 23), based on ratings and reviews from real travelers.
  • If you’re looking for a cheap vacation rental in Chester, you should consider visiting during the low season. The cheapest vacation homes in Chester can be found in April and January.
  • The cheapest night for renting a vacation home in Chester is Sunday. In contrast, the most expensive is Saturday.
  • Vacation rentals are a popular choice for both long and short-term stays. KAYAK users usually book their vacation rental in Chester for 2 days.
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FAQs when booking a vacation home in Chester

  • What types of vacation rentals are available in Chester?

    There are loads of different property types that you can make your vacation home in Chester. You’ll find cabins and houses.

  • Are there any pet-friendly vacation rentals in Chester?

    There are a number of dog and pet-friendly Chester vacation rentals, with around 18% allowing you to bring your pet along with you.

  • How can I find vacation rentals near me in Chester?

    Take a look at our vacation rentals map to find the best vacation rental homes 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 vacation rental.

Everything you need to know for your stay in Chester

Chester vacation rental deals. Search for vacation homes, apartments, condos, cabins, cottages, villas and more in Chester. Find cheap vacation homes to rent in Chester. KAYAK searches hundreds of travel sites to help you find and book a vacation rental in Chester that suits you best.

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