Gay friendly Hotels in Chester, New York

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Check availability on Chester Gay friendly Hotels

Tonight
Dec 31 - Jan 1
Tomorrow
Jan 1 - Jan 2
This weekend
Jan 2 - Jan 4
Next weekend
Jan 9 - Jan 11

Our top choices for Chester LGBT-friendly hotels

Exterior
Holiday Inn Express Hotel & Suites Chester by IHG

Holiday Inn Express Hotel & Suites Chester by IHG

Holiday Inn Express Hotel & Suites Chester by IHG
2.5 star property
Chester
8.6 out of 10, Excellent, (1002)
"timely & courteous check-in; clean rooms; quiet environment; perfect location for our needs "
United States
Orlando
The price is P7,353
P8,686 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Holiday Inn Express Hotel & Suites Chester by IHG
Miscellaneous
The Dominion House Bed & Breakfast

The Dominion House Bed & Breakfast

The Dominion House Bed & Breakfast
2.0 star property
Chester
9.2 out of 10, Wonderful, (233)
"Breakfast was delicious Suzy and Eric were wonderful hosts and the property is absolutely stunning highly recommend your bed and breakfast for those visiting upstate NY."
United States
Erek
The price is P12,647
P14,307 total
includes taxes & fees
Jan 12 - Jan 13, 2026
The Dominion House Bed & Breakfast
Exterior
Hampton Inn by Hilton Middletown

Hampton Inn by Hilton Middletown

Hampton Inn by Hilton Middletown
2.5 star property
Middletown
8.6 out of 10, Excellent, (1000)
"Room was clean and staff was great!"
United States
Annemarie
The price is P4,700
P5,552 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Hampton Inn by Hilton Middletown
Reception
Tru by Hilton Middletown

Tru by Hilton Middletown

Tru by Hilton Middletown
2.5 star property
Middletown
8.6 out of 10, Excellent, (961)
"Staff both during check in and out were great . Great stay ."
United States
david
The price is P5,258
P6,211 total
includes taxes & fees
Jan 7 - Jan 8, 2026
Tru by Hilton Middletown
Free daily continental breakfast
Quality Inn & Suites Fishkill South near I-84

Quality Inn & Suites Fishkill South near I-84

Quality Inn & Suites Fishkill South near I-84
2.5 star property
Fishkill
9.0 out of 10, Wonderful, (1001)
"Always stay here on my way through NY."
United States
Kathleen
The price is P5,250
P5,939 total
includes taxes & fees
Jan 9 - Jan 10, 2026
Quality Inn & Suites Fishkill South near I-84
Free daily buffet breakfast
Comfort Suites Fishkill near Interstate 84

Comfort Suites Fishkill near Interstate 84

Comfort Suites Fishkill near Interstate 84
2.5 star property
Fishkill
9.2 out of 10, Wonderful, (999)
"Yes stay was pleasant "
United States
henry
The price is P5,500
P6,222 total
includes taxes & fees
Jan 9 - Jan 10, 2026
Comfort Suites Fishkill near Interstate 84
Buffet
Holiday Inn Express Fishkill-Mid Hudson Valley by IHG

Holiday Inn Express Fishkill-Mid Hudson Valley by IHG

Holiday Inn Express Fishkill-Mid Hudson Valley by IHG
2.5 star property
Fishkill
8.4 out of 10, Very Good, (1000)
"Great customer service and breakfast was excellent "
United States
Dennis
The price is P5,294
P5,989 total
includes taxes & fees
Jan 24 - Jan 25, 2026
Holiday Inn Express Fishkill-Mid Hudson Valley by IHG
Indoor pool
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point

Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
2.0 star property
New Windsor
8.4 out of 10, Very Good, (1007)
"Superb place to stay."
United States
Denessy
The price is P5,347
P6,048 total
includes taxes & fees
Jan 13 - Jan 14, 2026
Red Roof Inn & Suites Newburgh – Stewart Airport/ West Point
View from property
Fairfield Inn & Suites by Marriott Goshen Middletown

Fairfield Inn & Suites by Marriott Goshen Middletown

Fairfield Inn & Suites by Marriott Goshen Middletown
2.5 star property
Goshen
8.8 out of 10, Excellent, (1001)
"Rooms were clean and as expected. Bed was a bit soft for our taste, but acceptable. Breakfast options were routine, scrambled eggs, bacon or sausage on alternating days, oatmeal, waffles, bagel, toast, English muffins... Pleasant and helpful staff, smooth check-in and check-out. Overall a pleasant place."
United States
Joon
The price is P6,177
P7,605 total
includes taxes & fees
Jan 11 - Jan 12, 2026
Fairfield Inn & Suites by Marriott Goshen Middletown
Lobby
Hilton Garden Inn Fishkill

Hilton Garden Inn Fishkill

Hilton Garden Inn Fishkill
3.0 star property
Fishkill
8.6 out of 10, Excellent, (1010)
"everything was great "
United States
Christopher
The price is P5,843
P6,610 total
includes taxes & fees
Jan 9 - Jan 10, 2026
Hilton Garden Inn Fishkill
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

Frequently asked questions

How do I find an LGBTQ-friendly hotel in Chester?
Consider this your open invitation to pack your bags and find LGBTQ-friendly hotels in Chester on Expedia. People like Chester for its shopping and restaurants.
What is the top LGBTQ-friendly hotel in Chester?
Holiday Inn Express Hotel & Suites Chester by IHG is a top LGBTQ-friendly hotel that features free breakfast and free WiFi. The Dominion House Bed & Breakfast is another good choice for your trip.
How many gay-friendly accommodations will I find in Chester?
You'll find 2 LGBTQ-friendly lodging options in Chester.
What should I do while I'm visiting Chester?
During your vacation, get out and explore all that Chester is known for. You and your traveling companions may want to visit Castle Fun Center, The Rock Sports Complex, and Museum Village. While you're here, create some great memories of your trip with a stop at Goosepond Mountain State Park.
What is an LGBTQ-friendly hotel in Chester?
LGBTQ-friendly hotels are places where lesbian, gay, bisexual, and transgender travelers are proudly welcomed. Expedia has worked with the International Gay and Lesbian Travel Association (IGLTA) to compile a selection of LGBTQ-friendly hotels worldwide. In Chester, hotels affiliated with IGLTA will provide lesbian, gay, bisexual, and transgender adventurers with the information needed to design the trip of a lifetime.
What can I expect from an LGBTQ-friendly accommodation in Chester?
Take a vacation from the ordinary; stay at an LGBTQ-friendly hotel in Chester, and you won't have to hide your same-sex relationship or your sexuality when you check-in. Many of our LGBTQ-friendly accommodations offer concierge services that provide information about nearby LGBTQ restaurants and local events.

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