Photo by Vincent Ramundo

Find Gay friendly Hotels in Middletown, NY

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

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check availability on Middletown Gay friendly Hotels

Tonight
Dec 28 - Dec 29
Tomorrow
Dec 29 - Dec 30
Next weekend
Jan 2 - Jan 4
In two weeks
Jan 9 - Jan 11

Our top choices for Middletown LGBT-friendly hotels

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, (1005)
"Room was clean and staff was great!"
United States
Annemarie
The price is ₩104,160
₩123,039 total
includes taxes & fees
Jan 4 - Jan 5, 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, (959)
"Staff both during check in and out were great . Great stay ."
United States
david
The price is ₩136,367
₩161,083 total
includes taxes & fees
Jan 16 - Jan 17, 2026
Tru by Hilton Middletown
Courtyard
Home2 Suites by Hilton Middletown

Home2 Suites by Hilton Middletown

Home2 Suites by Hilton Middletown
3.0 star property
Middletown
9.0 out of 10, Wonderful, (747)
"Staff was really amazing. They worked hard and were great all week long. "
United States
Joshua
The price is ₩237,413
₩285,491 total
includes taxes & fees
Jan 1 - Jan 2, 2026
Home2 Suites by Hilton Middletown
View from property
Residence Inn by Marriott Middletown Goshen

Residence Inn by Marriott Middletown Goshen

Residence Inn by Marriott Middletown Goshen
3.0 star property
Middletown
9.4 out of 10, Exceptional, (317)
"Room and service were excellent."
United States
Cymantha
The price is ₩245,082
₩289,504 total
includes taxes & fees
Jan 12 - Jan 13, 2026
Residence Inn by Marriott Middletown Goshen
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, (1007)
"timely & courteous check-in; clean rooms; quiet environment; perfect location for our needs "
United States
Orlando
The price is ₩121,099
₩143,048 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Holiday Inn Express Hotel & Suites Chester by IHG
Lobby
Hampton Inn Harriman Woodbury

Hampton Inn Harriman Woodbury

Hampton Inn Harriman Woodbury
2.5 star property
Central Valley
9.2 out of 10, Wonderful, (1019)
"Great stay and room was very nice"
United States
Emmanuel
The price is ₩140,677
₩173,207 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Hampton Inn Harriman Woodbury
Exterior
Hampton Inn Monticello

Hampton Inn Monticello

Hampton Inn Monticello
2.5 star property
Monticello
9.4 out of 10, Exceptional, (623)
"Friendly staff, and room is big"
United States
Yujing
The price is ₩164,320
₩185,682 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Hampton Inn Monticello
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, (1003)
"Love it, everytime we come this is the place to stay"
United States
William
The price is ₩145,593
₩164,703 total
includes taxes & fees
Jan 1 - Jan 2, 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 ₩145,608
₩179,281 total
includes taxes & fees
Jan 6 - Jan 7, 2026
Fairfield Inn & Suites by Marriott Goshen Middletown
Free daily buffet breakfast
Best Western Monticello

Best Western Monticello

Best Western Monticello
2.5 star property
Monticello
8.2 out of 10, Very Good, (1001)
"Awesome place to stay"
Canada
Mitchell
The price is ₩133,209
₩150,525 total
includes taxes & fees
Jan 4 - Jan 5, 2026
Best Western Monticello
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 Middletown Hotel Reviews

Frequently asked questions

Looking for a gay-friendly hotel in Middletown?
Book a place where you can be yourself! You'll find gay-friendly hotels in Middletown on Expedia. The restaurants is something travelers enjoy about this welcoming area.
What is the top LGBTQ-friendly hotel in Middletown?
Hampton Inn by Hilton Middletown is a top LGBTQ-friendly hotel that features free breakfast and free WiFi. Home2 Suites by Hilton Middletown and Residence Inn by Marriott Middletown Goshen are other good choices for your trip.
How many LGBTQ-friendly hotels are there in Middletown?
There are currently 4 gay-friendly hotels in Middletown.
What should I see while I'm in Middletown?
During your vacation, get out and explore everything Middletown is known for. You and your traveling companions may want to visit Paramount Theatre, Orange County Fair Speedway, and Orange County Fairgrounds. While you're here, create some great memories of your trip with stops at Galleria at Crystal Run, Highland Lakes State Park, and Highland Lake.
What is an LGBTQ-friendly hotel in Middletown?
LGBTQ-friendly hotels welcome all travelers who identify as LGBTQIA+. Expedia has compiled a selection of LGBTQ-friendly hotels worldwide. In Middletown, these hotels operate in a spirit of inclusiveness, prioritizing a diverse environment in which guests are welcomed, respected, and not obliged to declare or hide their sexual orientation.
What can I expect from a gay-friendly hotel in Middletown?
Take a vacation from the ordinary; stay at an LGBTQ-friendly hotel in Middletown, 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.