Airbnb, Vacation Rentals in Chester, NY

Compare 798 available vacation home properties, starts from $12

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ACCOMMODATION TYPES

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Airbnb, Vacation rentals and hotel deals in Chester, NY

Red Roof Inn & Suites Newburgh - Stewart Airport
Red Roof Inn & Suites Newburgh - Stewart Airport
Red Roof Inn & Suites Newburgh - Stewart Airport
Red Roof Inn & Suites Newburgh - Stewart Airport
8.3 (631 reviews)
Red Roof Inn & Suites Newburgh - Stewart Airport
Motel · 2 Guests · 1 Bedroom
$132 /night
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A romantic cottage and artist's retreat looking down over an enchanted lake
A romantic cottage and artist's retreat looking down over an enchanted lake
A romantic cottage and artist's retreat looking down over an enchanted lake
A romantic cottage and artist's retreat looking down over an enchanted lake
9.4 (89 reviews)
A romantic cottage and artist's retreat looking down over an enchanted lake
Cottage · 2 Guests · 1 Bedroom
$125 /night*
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Ramada by Wyndham Newburgh/West Point
Ramada by Wyndham Newburgh/West Point
Ramada by Wyndham Newburgh/West Point
Ramada by Wyndham Newburgh/West Point
5.7 (394 reviews)
Ramada by Wyndham Newburgh/West Point
Hotel · 2 Guests · 1 Bedroom
$95 /night
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Howard Johnson by Wyndham Newburgh
Howard Johnson by Wyndham Newburgh
Howard Johnson by Wyndham Newburgh
Howard Johnson by Wyndham Newburgh
5.8 (585 reviews)
Howard Johnson by Wyndham Newburgh
Hotel · 2 Guests · 1 Bedroom
$111 /night
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2 bedroom cozy condo with parking on premises
2 bedroom cozy condo with parking on premises
2 bedroom cozy condo with parking on premises
2 bedroom cozy condo with parking on premises
9.6 (4 reviews)
2 bedroom cozy condo with parking on premises
Condo · 2 Guests · 1 Bedroom
$145 /night*
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Holiday Inn Express and Suites Montgomery, an IHG Hotel
Holiday Inn Express and Suites Montgomery, an IHG Hotel
Holiday Inn Express and Suites Montgomery, an IHG Hotel
Holiday Inn Express and Suites Montgomery, an IHG Hotel
8.3 (143 reviews)
Holiday Inn Express and Suites Montgomery, an IHG Hotel
Hotel · 2 Guests · 1 Bedroom
$162 /night
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1786 Farm Cottage "Honeymoon Suite" Renovated 2022
1786 Farm Cottage "Honeymoon Suite" Renovated 2022
1786 Farm Cottage "Honeymoon Suite" Renovated 2022
1786 Farm Cottage "Honeymoon Suite" Renovated 2022
1786 Farm Cottage "Honeymoon Suite" Renovated 2022
Holiday home · 2 Guests · 1 Bedroom
$199 /night*
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Tru By Hilton Middletown
Tru By Hilton Middletown
Tru By Hilton Middletown
Tru By Hilton Middletown
7.7 (320 reviews)
Tru By Hilton Middletown
Hotel · 2 Guests · 1 Bedroom
$112 /night
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Hidden Gem
Hidden Gem
Hidden Gem
Hidden Gem
Hidden Gem
Apartment · 2 Guests · 1 Bedroom
$122 /night*
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Sleep Inn & Suites Middletown - Goshen
Sleep Inn & Suites Middletown - Goshen
Sleep Inn & Suites Middletown - Goshen
Sleep Inn & Suites Middletown - Goshen
8.1 (264 reviews)
Sleep Inn & Suites Middletown - Goshen
Hotel · 2 Guests · 1 Bedroom
$115 /night
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Overlook Lodge and Stone Cottages at Bear Mountain
Overlook Lodge and Stone Cottages at Bear Mountain
Overlook Lodge and Stone Cottages at Bear Mountain
Overlook Lodge and Stone Cottages at Bear Mountain
7.7 (425 reviews)
Overlook Lodge and Stone Cottages at Bear Mountain
Hotel · 2 Guests · 1 Bedroom
$130 /night
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Little Getaway at Mountain Creek Sanctuary
Little Getaway at Mountain Creek Sanctuary
Little Getaway at Mountain Creek Sanctuary
Little Getaway at Mountain Creek Sanctuary
10 (1 review)
Little Getaway at Mountain Creek Sanctuary
Condo · 2 Guests · 1 Bedroom
$163 /night*
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Microtel Inn & Suites by Wyndham Middletown
Microtel Inn & Suites by Wyndham Middletown
Microtel Inn & Suites by Wyndham Middletown
Microtel Inn & Suites by Wyndham Middletown
7.2 (1053 reviews)
Microtel Inn & Suites by Wyndham Middletown
Hotel · 2 Guests · 1 Bedroom
$76 /night
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Courtyard by Marriott Middletown Goshen
Courtyard by Marriott Middletown Goshen
Courtyard by Marriott Middletown Goshen
Courtyard by Marriott Middletown Goshen
8.8 (193 reviews)
Courtyard by Marriott Middletown Goshen
Hotel · 2 Guests · 1 Bedroom
$128 /night
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Courtyard by Marriott Newburgh Stewart Airport
Courtyard by Marriott Newburgh Stewart Airport
Courtyard by Marriott Newburgh Stewart Airport
Courtyard by Marriott Newburgh Stewart Airport
7.3 (79 reviews)
Courtyard by Marriott Newburgh Stewart Airport
Hotel · 2 Guests · 1 Bedroom
$149 /night
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Budget Motor Inn- Stony Point
Budget Motor Inn- Stony Point
Budget Motor Inn- Stony Point
Budget Motor Inn- Stony Point
4.4 (139 reviews)
Budget Motor Inn- Stony Point
Motel · 2 Guests · 1 Bedroom
$72 /night
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Inn on the Hudson
Inn on the Hudson
Inn on the Hudson
Inn on the Hudson
6.2 (458 reviews)
Inn on the Hudson
Hotel · 2 Guests · 1 Bedroom
$102 /night
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Beacon Hotel
Beacon Hotel
Beacon Hotel
Beacon Hotel
6.2 (9 reviews)
Beacon Hotel
Hotel · 2 Guests · 1 Bedroom
$145 /night
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The Borland House Inn
The Borland House Inn
The Borland House Inn
The Borland House Inn
8.5 (30 reviews)
The Borland House Inn
B & B · 2 Guests · 1 Bedroom
$191 /night
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Stay in the heart of Greenwood Lake minutes away from the lake
Stay in the heart of Greenwood Lake minutes away from the lake
Stay in the heart of Greenwood Lake minutes away from the lake
Stay in the heart of Greenwood Lake minutes away from the lake
9.6 (4 reviews)
Stay in the heart of Greenwood Lake minutes away from the lake
Apartment · 2 Guests · 1 Bedroom
$133 /night*
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Vacation Destinations Near Chester, NY

Airbnb, Vacation House with Air Conditioning in Chester, NY

The Cottage at Glenwood Retreats
The Cottage at Glenwood Retreats
The Cottage at Glenwood Retreats
The Cottage at Glenwood Retreats
Air Conditioning
The Cottage at Glenwood Retreats
Holiday home · 2 Guests · 1 Bedroom
$508 /night
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Cromwell Manor Inn
Cromwell Manor Inn
Cromwell Manor Inn
Cromwell Manor Inn
Air Conditioning
9.8 (21 reviews)
Cromwell Manor Inn
B & B · 2 Guests · 1 Bedroom
$242 /night
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Alpine Haus Bed & Breakfast Inn
Alpine Haus Bed & Breakfast Inn
Alpine Haus Bed & Breakfast Inn
Alpine Haus Bed & Breakfast Inn
Air Conditioning
9.0 (283 reviews)
Alpine Haus Bed & Breakfast Inn
B & B · 2 Guests · 1 Bedroom
$181 /night
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What Are The Top Amenities at Chester, NY?
Amenity Info in Chester, NY
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There are in total of 16 rental amenities in Chester, shown above with the property numbers. In Chester, 352 rentals offer Internet or Wifi, 332 rentals offer Heater, 332 rentals offer Parking Available. So, if you need Internet or Wifi during your vacation, use the Internet or Wifi filter to compare these properties. Two amenities that are not typical are Kitchen, Hot Tub.
Which Price Range Is Most Typical in Chester, NY Area?
Vacation House & Condo Rental Price Information in Chester, NY
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The graph shows the percentages of vacation homes in each price bucket. Chester has the largest percentage (17.81%) of homes in $150 - $200 price range.
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$500 +
$500 +
What Are The Most Liked Rental Accommodations in Chester, NY?
Best Accommodation Types in Chester, NY
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There are various types of homes in Chester area. Depending on your group size, you can pick the one using filters accordingly. House is the most popular accommodation type, and the largest homes can accommodate 32 people.The least popular accommodation in Chester is Boat rentals
How Many Accommodations Are Not Pets Friendly in Chester, NY?
Pets Allowed vs Not Allowed in Chester, NY
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25.06% of vacation homes in Chester are pet friendly. Make sure you select the pet friendly home filter when you are going to bring your pet(s) for the upcoming vacation.
Must-Visit Trails in Chester, NY?
Best Trails In Chester, NY
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The most visited trails here in Chester are: Glenmere Lake, Birnberg Nature Preserve Trail, Goose Pond Mountain - Bike Trails, Goose Pond Mountain Trail, Orange Heritage Trail, Appalachian Trail: Fitzgerald Falls to Little Dam Lake, Earl Reservoir Loop, Appalachian Trail (Dutch Hollow & Harriman State Park), Appalachian Trail:17A to Seven Lakes, Furnace and Indian Hill Loop Trail.
Where Are The Campgrounds in Chester, NY Area?
Campgrounds Recommendations In Chester, NY
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For campgrounds in Chester, here are our recommendations: Mountaindale Campground, New York City North / Newburgh KOA, Korn's Campgrounds, Deerpark / New York City NW KOA, Black Bear Campground, Black Bear Campground, Woodland Trails Campground, Pleasant Acres Farm Campground, Tall Timbers Campground, Harmony Ridge Campground.
How Many Airports in Chester, NY?
Airports Options in Chester, NY
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Airbnb, Vacation House with Fireplace in Chester, NY

Gorgeous Montgomery Home With Hot Tub!
Gorgeous Montgomery Home With Hot Tub!
Gorgeous Montgomery Home With Hot Tub!
Gorgeous Montgomery Home With Hot Tub!
Fireplace
Gorgeous Montgomery Home With Hot Tub!
Cottage · 2 Guests · 1 Bedroom
$849 /night
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East End Cottage - Charming escape in Newburgh
East End Cottage - Charming escape in Newburgh
East End Cottage - Charming escape in Newburgh
East End Cottage - Charming escape in Newburgh
Fireplace
10 (1 review)
East End Cottage - Charming escape in Newburgh
Holiday home · 2 Guests · 1 Bedroom
$254 /night*
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Waterfront Showcase Home with Incredible Lake Views
Waterfront Showcase Home with Incredible Lake Views
Waterfront Showcase Home with Incredible Lake Views
Waterfront Showcase Home with Incredible Lake Views
Fireplace
9.6 (47 reviews)
Waterfront Showcase Home with Incredible Lake Views
Holiday home · 2 Guests · 1 Bedroom
$800 /night*
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Airbnb, Vacation Condo with Pool, and Other Rental Options in Chester, NY

Mountain Creek Resort | Fireplace | Free Wifi | 04-11
Mountain Creek Resort | Fireplace | Free Wifi | 04-11
Mountain Creek Resort | Fireplace | Free Wifi | 04-11
Mountain Creek Resort | Fireplace | Free Wifi | 04-11
Pool
10 (8 reviews)
Mountain Creek Resort | Fireplace | Free Wifi | 04-11
Condo · 2 Guests · 1 Bedroom
$399 /night*
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Mountain Creek Resort| Pool | Hot Tubs | Gym | Café |Wineries | Hiking | 220
Mountain Creek Resort| Pool | Hot Tubs | Gym | Café |Wineries | Hiking | 220
Mountain Creek Resort| Pool | Hot Tubs | Gym | Café |Wineries | Hiking | 220
Mountain Creek Resort| Pool | Hot Tubs | Gym | Café |Wineries | Hiking | 220
Pool
Mountain Creek Resort| Pool | Hot Tubs | Gym | Café |Wineries | Hiking | 220
Condo · 2 Guests · 1 Bedroom
$265 /night*
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Mountain Creek/Great Gorge Village 3 Bedroom Condo
Mountain Creek/Great Gorge Village 3 Bedroom Condo
Mountain Creek/Great Gorge Village 3 Bedroom Condo
Mountain Creek/Great Gorge Village 3 Bedroom Condo
Pool
8.2 (19 reviews)
Mountain Creek/Great Gorge Village 3 Bedroom Condo
Condo · 2 Guests · 1 Bedroom
$217 /night*
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* The displayed nightly rate may be estimated based on a future travel date. Narrow down your search with checkin and checkout dates to see the exact price.
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