Vacation Rentals in Chester, NY
PRICE PER NIGHT
ACCOMMODATION TYPES
Secluded Spacious NY Getaway, 1 hour from NYC
8.9
Very good
·
Chester
·
6 br
·
Sleeps 14
·
High Ceilings · Fitness Center · Private Pool ·
From
$1,050/nightProperty
House · 6 Beds · 6 baths
Amenities
High Ceilings
Fitness Center
Private Pool
On Site Laundry
Hardwood Floor
Pool
Fireplace
Dishwasher
Other spaces
Balcony, Kitchen
Holiday Inn Express Hotel & Suites Chester, an IHG Hotel
8
Very good
·
Chester
·
1 br
·
Sleeps 6
·
Assigned Parking · Smoking Allowed · Free Parking ·
From
$83/nightProperty
Hotel · 1 Bed
Amenities
Assigned Parking
Smoking Allowed
Free Parking
On Site Laundry
Pool
Air Conditioning
Furnished
Wifi
Other spaces
Workspace
Luxury Apt Sugar Loaf, Near LEGOLAND, Breweries & Wineries
10
Excellent
·
Chester
·
2 br
·
Sleeps 6
·
Hardwood Floor · Balcony · Workspace ·
From
$178/nightProperty
Apartment · 2 Beds · 2 baths
Amenities
Hardwood Floor
Dishwasher
In Unit Laundry
Oven
Air Conditioning
Furnished
Wifi
Other spaces
Balcony, Workspace, Kitchen
Magnificent Villa, Private Pool, Fire Pit w/Huge Backyard
8.7
Very good
·
Chester
·
3 br
·
Sleeps 16
·
Outdoor Space · Pool · Fireplace ·
From
$1,333/nightProperty
Apartment · 3 Beds · 5 baths
Amenities
Pool
Fireplace
Dishwasher
In Unit Laundry
Oven
Air Conditioning
Furnished
Wifi
Other spaces
Workspace, Kitchen
Harmony Hambletonian-A Luxury Retreat Back in Time
No reviews
·
Chester
·
7 br
·
Sleeps 14
·
Fireplace · Balcony · Dishwasher ·
From
$1,065/nightProperty
Apartment · 7 Beds · 5 baths
Amenities
Fireplace
Dishwasher
In Unit Laundry
Oven
Air Conditioning
Furnished
Wifi
Swimming Pool
Other spaces
Balcony, Kitchen
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Luxurious & Peaceful ~ Pool ~ Fire Pit ~ Backyard!
No reviews
·
Monroe
·
6 br
·
Sleeps 16
·
Carpet · Assigned Parking · Private Pool ·
From
$474/nightProperty
House · 6 Beds · 4 baths
Amenities
Carpet
Assigned Parking
Private Pool
Free Parking
On Site Laundry
Hardwood Floor
Pool
Fireplace
Other spaces
Workspace, Kitchen
Hudson Valley Mid Century Bungalow 1 hr from NYC
No reviews
·
Monroe
·
2 br
·
Sleeps 5
·
Outdoor Space · Fireplace · Workspace ·
From
$181/nightProperty
House · 2 Beds · 2 baths
Amenities
Fireplace
Dishwasher
In Unit Laundry
Oven
Air Conditioning
Furnished
Wifi
Storage
Other spaces
Workspace, Kitchen
Unique Scenic home with king suite & hot tub
No reviews
·
Monroe
·
5 br
·
Sleeps 11
·
Outdoor Space · Fireplace · Balcony ·
From
$492/nightProperty
House · 5 Beds · 3 baths
Amenities
Fireplace
Dishwasher
In Unit Laundry
Oven
Air Conditioning
Furnished
Wifi
Swimming Pool
Other spaces
Balcony, Kitchen
Elmwood Home - Pool, Firepit, 5 min to Legoland, located in beautiful Goshen, NY
No reviews
·
Goshen
·
3 br
·
Sleeps 6
·
Outdoor Space · Pool · Balcony ·
From
$256/nightProperty
House · 3 Beds · 2 baths
Amenities
Pool
Dishwasher
In Unit Laundry
Oven
Air Conditioning
Furnished
Wifi
Swimming Pool
Other spaces
Balcony, Kitchen
Goshen Renovated 5 Bedroom Country Home
10
Excellent
·
Goshen
·
5 br
·
Sleeps 10
·
Dishwasher · In Unit Laundry · Kitchen ·
From
$482/nightProperty
House · 5 Beds · 3 baths
Amenities
Dishwasher
In Unit Laundry
Oven
Air Conditioning
Furnished
Wifi
Other spaces
Kitchen
The Twin Lakes House - Lake view
No reviews
·
Monroe
·
7 br
·
Sleeps 14
·
High Ceilings · Hardwood Floor · Fireplace ·
From
$944/nightProperty
Apartment · 7 Beds · 4 baths
Amenities
High Ceilings
Hardwood Floor
Fireplace
Dishwasher
In Unit Laundry
Oven
Air Conditioning
Furnished
Other spaces
Kitchen
Newly Renovated Gorgeous Home in Goshen
9.4
Excellent
·
Goshen
·
3 br
·
Sleeps 6
·
Dishwasher · In Unit Laundry · Kitchen ·
From
$300/nightProperty
House · 3 Beds · 2 baths
Amenities
Dishwasher
In Unit Laundry
Oven
Air Conditioning
Furnished
Wifi
Other spaces
Kitchen
Awesome Country Retreat - 5BR - Private and Peaceful
No reviews
·
Monroe
·
4 br
·
Sleeps 9
·
Fireplace · Dishwasher · In Unit Laundry ·
From
$292/nightProperty
Apartment · 4 Beds · 3 baths
Amenities
Fireplace
Dishwasher
In Unit Laundry
Oven
Air Conditioning
Furnished
Wifi
Storage
Other spaces
Kitchen
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Sleep Inn & Suites Monroe - Woodbury
8.8
Very good
·
Monroe
·
1 br
·
Sleeps 4
·
Carpet · Smoking Allowed · Free Parking ·
From
$84/nightProperty
Hotel · 1 Bed
Amenities
Carpet
Smoking Allowed
Free Parking
On Site Laundry
Fireplace
Air Conditioning
Furnished
Wifi
Other spaces
Workspace
A One Eyed Horse farm - Historic house and ANIMAL SANCTUARY
No reviews
·
Warwick
·
4 br
·
Sleeps 10
·
Outdoor Space · Workspace · Dishwasher ·
From
$375/nightProperty
House · 4 Beds · 3 baths
Amenities
Dishwasher
In Unit Laundry
Oven
Air Conditioning
Furnished
Wifi
Other spaces
Workspace, Kitchen
NATURE'S NIRVANA FOR FAMILY AND FRIEND
9.4
Excellent
·
Monroe
·
1 br
·
Sleeps 6
·
Private Pool · Outdoor Space · Pool ·
From
$128/nightProperty
Apartment · 1 Bed · 1 bath
Amenities
Private Pool
Pool
Fireplace
In Unit Laundry
Oven
Air Conditioning
Furnished
Wifi
Other spaces
Balcony, Workspace, Kitchen
Mesmerizing and Luxurious Home
No reviews
·
Goshen
·
4 br
·
Sleeps 12
·
Kitchen · Furnished · Swimming Pool ·
From
$691/nightProperty
House · 4 Beds · 5 baths
Amenities
Furnished
Swimming Pool
Other spaces
Kitchen
Luxurious & Tranquil ~ Pool ~ Fire Pit ~ Backyard!
No reviews
·
Monroe
·
5 br
·
Sleeps 14
·
Private Pool · Pool · Fireplace ·
From
$530/nightProperty
Apartment · 5 Beds · 3 baths
Amenities
Private Pool
Pool
Fireplace
Dishwasher
In Unit Laundry
Oven
Furnished
Wifi
Other spaces
Workspace, Kitchen
NEW! Lakefront New York Home w/ Boat Dock!
No reviews
·
Monroe
·
4 br
·
Sleeps 6
·
Ceiling Fan · Lake · Waterfront ·
From
$320/nightProperty
House · 4 Beds · 2 baths
Amenities
Ceiling Fan
Lake
Waterfront
Fireplace
Dishwasher
In Unit Laundry
Oven
Air Conditioning
Other spaces
Kitchen
Unique Dutch Barn in the Hudson Valley
10
Excellent
·
Goshen
·
5 br
·
Sleeps 12
·
Ski In Ski Out · Fitness Center · High Ceilings ·
From
$395/nightProperty
House · 5 Beds · 3 baths
Amenities
Ski In Ski Out
Fitness Center
High Ceilings
On Site Laundry
Fireplace
Dishwasher
In Unit Laundry
Oven
Other spaces
Workspace, Kitchen
Guesthouse 2 bedroom. 25min-West Point
No reviews
·
Chester
·
2 br
·
Sleeps 4
·
Dishwasher · In Unit Laundry · Kitchen ·
From
$112/nightProperty
House · 2 Beds · 1 bath
Amenities
Dishwasher
In Unit Laundry
Oven
Air Conditioning
Furnished
Wifi
Other spaces
Kitchen
The Artsy Cottage-Lovely Rustic Modern by the Lake
No reviews
·
Monroe
·
2 br
·
Sleeps 6
·
In Unit Laundry · Air Conditioning · Furnished ·
From
$290/nightProperty
Apartment · 2 Beds · 1 bath
Amenities
In Unit Laundry
Air Conditioning
Furnished
Wifi
A hidden creek in Monroe
No reviews
·
Monroe
·
2 br
·
Sleeps 4
·
Hot Tub · Pool · In Unit Laundry ·
From
$2,050/nightProperty
House · 2 Beds · 2 baths
Amenities
Hot Tub
Pool
In Unit Laundry
Air Conditioning
Furnished
Wifi
Onsite Management
Swimming Pool
Modern, peaceful House in Monroe
No reviews
·
Monroe
·
7 br
·
Sleeps 16
·
Fireplace · In Unit Laundry · Kitchen ·
From
$856/nightProperty
House · 7 Beds · 4 baths
Amenities
Fireplace
In Unit Laundry
Oven
Air Conditioning
Furnished
Wifi
Swimming Pool
Other spaces
Kitchen
Updated: March 25, 2023
Learn about vacation rentals in
Chester
Explore 6 vacation rentals near Chester, New York. Whether you’re a tourist or on a staycation, there’s plenty of things to do and restaurants to try around the city. If you’re looking to take a trip to Chester, you can see photos of Chester vacation rentals, view amenities and features, browse by specific property types, and more. Use our interactive map to find Chester vacation rentals in specific areas. Whether you’re looking for a Chester staycation, weekend getaway, or a long vacation, we’ve got you covered. Use the date filters at the top to select your travel dates and view availability. The lowest vacation rental price in Chester is $83 per night and the highest price is $1,333 per night.
1 of the vacation rentals near Chester are houses.
The average bathroom count for a vacation house near Chester is
6. The average price for vacation houses near Chester is $1,050 per night. There are 1 vacation homes under this price. The most common
amenities for vacation rentals near Chester are: furnished, wifi, and air conditioning. To find vacation properties that might be a good option for large groups or families, use our filters for bedroom count, bathroom count and more.
1 bed rentals
2 available
2 bed rentals
1 available
3 bed rentals
1 available
4+ bed rentals
2 available
Getting around Chester
Walking
3/10
Fewer daily needs are within walking distance (unless you’re up for a challenge).
Car
10/10
Commuting is easy with multiple accessible routes and plenty of parking.
Points of interest in Chester
Groceries
3/10
At least one grocery store within a 30-minute walk
Shopping
2/10
Few or no shops within walking distance
Cafes
3/10
Few or no cafés within walking distance
Restaurants
4/10
Some restaurants within walking distance
Nightlife
3/10
Few or no bars within walking distance
Vacation Rentals in Chester, NY FAQ
How many vacation rentals in Chester are available?
There are currently 6 vacation rentals in Chester available. Our vacation rentals in Chester include nightly rentals, weekend rentals, weekly rentals, and monthly rentals.
Are there any pet friendly vacation rentals in Chester?
No, right now there are no pet friendly vacation rentals in Chester. A pet friendly vacation rental in Chester means a rental home that is dog friendly or cat friendly. Some pet friendly homes may accommodate other types of pets, as well. Contact the listing agent for any pet related inquiries.
Are there any vacation rentals in Chester with a pool?
Yes there are vacation rentals with a pool available in Chester, NY. View more detailed vacation spots on Vacations by Zumper.
Are there any vacation rentals in Chester with internet access?
As of March 25, 2023, there are vacation rentals with internet access available in Chester, New York. Check out more enjoyable destinations on Vacations by Zumper.
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