Chester vacation rentals

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Best Chester vacation rentals

Most recommended vacation rentals in Chester

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Spacious Suite (1 hr to Manhattan) - Chester - Bedroom
Spacious Suite (1 hr to Manhattan)
Chester, NY
$126+
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6 bedroom colonial house - Chester - Building
6 bedroom colonial house
Chester, NY
Free Wi-Fi
$711+
Check availability
Guesthouse 2 bedroom. 25min-West Point - Chester - Stairs
Guesthouse 2 bedroom. 25min-West Point
Chester, NY
Pet friendly
$183+
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Luxury Apt Sugar Loaf, Near Legoland, Breweries & Wineries - Chester - Kitchen
Luxury Apt Sugar Loaf, Near Legoland, Breweries & Wineries
Chester, NY
Free Wi-Fi
$305+
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Summerville Getaway (30 min to Mt. Creek) - Chester - Living room
Summerville Getaway (30 min to Mt. Creek)
Chester, NY
$546+
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Magnificent Villa, Private Pool, Fire Pit w/Huge Backyard - Chester - Living room
Magnificent Villa, Private Pool, Fire Pit w/Huge Backyard
Chester, NY
Free Wi-Fi
$1,752+
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Millionare Mansion w/ Lrg Hot Tub on 1.5 Acres - fun activities all around! - Chester - Living room
Millionare Mansion w/ Lrg Hot Tub on 1.5 Acres - fun activities all around!
Chester, NY
Free Wi-Fi
$557+
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Elegant Home 7brs, Game Room, Luxury Yard, Pool - Chester - Living room
Elegant Home 7brs, Game Room, Luxury Yard, Pool
Chester, NY
Parking
Free Wi-Fi
Pool
$1,034+
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Secluded 9br Getaway, Pool, Hot Tub & Huge Deck - Chester - Living room
Secluded 9br Getaway, Pool, Hot Tub & Huge Deck
Chester, NY
Parking
Free Wi-Fi
Pool
Pet friendly
$1,287+
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1786 Farm Cottage Honeymoon Suite Renovated 2022 - Chester
1786 Farm Cottage Honeymoon Suite Renovated 2022
Chester, NY
9.0Wonderful(6)
Parking
Free Wi-Fi
$240+
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Secluded Spacious Ny Getaway, 1 Hour From Nyc - Chester
Secluded Spacious Ny Getaway, 1 Hour From Nyc
Chester, NY
Pool
$1,156+
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Craftsman Hideaway at the 1841 Farmhouse - Chester
Craftsman Hideaway at the 1841 Farmhouse
Chester, NY
9.2Wonderful(4)
Parking
Free Wi-Fi
$240+
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Very Private Large Home on 22 Acres - Chester
Very Private Large Home on 22 Acres
Chester, NY
Parking
Free Wi-Fi
Pet friendly
$424+
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$0 - $438$438 - $876$876 - $1,314$1,314 - $1,752$1,752+ per night

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Good to know

Low season

January

High season

February

Average price (weeknight)

$494

Average price (weekend night)

$136
Cheapest month to stay with an average 60% drop in price.
Most expensive month to stay with an average 153% 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

  • Vacation rentals in Chester are around 75% more expensive than hotels on average. Search here to compare prices for all accommodation types in Chester.
  • The best vacation rental property in Chester is Luxury Apt Sugar Loaf, Near Legoland, Breweries & Wineries (9.9, 20 reviews), 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 January and May.
  • The cheapest night for renting a vacation home in Chester is Friday. In contrast, the most expensive is Monday.
  • Vacation rentals are a popular choice for both long and short-term stays. KAYAK users usually book their vacation rental in Chester for 10 days.

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 agritourism, apartments, houses and villas.

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

    There are a number of dog and pet-friendly Chester vacation rentals, with around 17% 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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