Find Winery Hotels in Chester, NY

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check availability on Chester Winery Hotels

Tonight
1 Oct - 2 Oct
Tomorrow
2 Oct - 3 Oct
This weekend
3 Oct - 5 Oct
Next weekend
10 Oct - 12 Oct

Top Chester Winery Hotels

Holiday Inn Express & Suites Montgomery by IHG
Exterior

Holiday Inn Express & Suites Montgomery by IHG

2.5 star property
8.8 out of 10, Excellent, (767)
"We really like the hotel and area very safe"
The price is AED 430
AED 486 total
includes taxes & fees
19 Oct - 20 Oct
Holiday Inn Express & Suites Montgomery by IHG
Borland House Inn
Exterior detail

Borland House Inn

3.0 star property
9.2 out of 10, Wonderful, (128)
"Unique experience, very comfortable, clean and quaint"
Borland House Inn
Hampton Inn Fishkill
Exterior

Hampton Inn Fishkill

2.5 star property
8.6 out of 10, Excellent, (1000)
"Nice place"
The price is AED 481
AED 544 total
includes taxes & fees
30 Oct - 31 Oct
Hampton Inn Fishkill
Courtyard by Marriott Newburgh Stewart Airport
Exterior

Courtyard by Marriott Newburgh Stewart Airport

3.0 star property
8.2 out of 10, Very Good, (681)
"Great stay!"
The price is AED 466
AED 551 total
includes taxes & fees
13 Oct - 14 Oct
Courtyard by Marriott Newburgh Stewart Airport
Hilton Garden Inn Fishkill
Lobby

Hilton Garden Inn Fishkill

3.0 star property
8.6 out of 10, Excellent, (1012)
"It was a great place to stay "
The price is AED 496
AED 562 total
includes taxes & fees
7 Oct - 8 Oct
Hilton Garden Inn Fishkill
The Orange Inn Boutique Hotel
Restaurant

The Orange Inn Boutique Hotel

2.0 star property
9.6 out of 10, Exceptional, (145)
"Very spacious room, friendly staff, modern touches"
The Orange Inn Boutique Hotel
Sonesta Simply Suites Nanuet
Terrace/patio

Sonesta Simply Suites Nanuet

2.5 star property
8.4 out of 10, Very Good, (1038)
"Great place to stay!!"
The price is AED 393
AED 457 total
includes taxes & fees
7 Oct - 8 Oct
Sonesta Simply Suites Nanuet
Holiday Inn Express & Suites Middletown - Goshen by IHG
Free daily continental breakfast

Holiday Inn Express & Suites Middletown - Goshen by IHG

2.5 star property
8.8 out of 10, Excellent, (690)
"great clean stay"
The price is AED 572
AED 676 total
includes taxes & fees
5 Oct - 6 Oct
Holiday Inn Express & Suites Middletown - Goshen by IHG
Hampton Inn & Suites Newburgh Stewart Airport
Reception

Hampton Inn & Suites Newburgh Stewart Airport

2.5 star property
9.2 out of 10, Wonderful, (950)
"Nice place to stay! "
The price is AED 592
AED 700 total
includes taxes & fees
13 Oct - 14 Oct
Hampton Inn & Suites Newburgh Stewart Airport
Home2 Suites by Hilton Middletown
Courtyard

Home2 Suites by Hilton Middletown

3.0 star property
9.0 out of 10, Wonderful, (727)
"Staff was very friendly and checked in daily to make sure you were comfortable and didn’t need anything "
The price is AED 559
AED 673 total
includes taxes & fees
13 Oct - 14 Oct
Home2 Suites by Hilton Middletown
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties

Top Chester Hotel Reviews

Hampton Inn Harriman Woodbury

Hampton Inn Harriman Woodbury

10/10 Excellent
"Good "
Shuang 1-night trip
Posted 4 days ago
Hampton Inn Harriman Woodbury
Quality Inn & Suites Fishkill South near I-84

Quality Inn & Suites Fishkill South near I-84

10/10 Excellent
"Convenient, great parking, quiet, comfortable room with a friendly staff."
Gay 2-night trip
Posted 7 days ago
Quality Inn & Suites Fishkill South near I-84

Explore a world of travel with Expedia

Explore a world of travel with Expedia