Search Gay-Friendly Hotels in Chestertown

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Check availability on Chestertown Gay-Friendly Hotels

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

Our top choices for Chestertown LGBT-friendly hotels

Lobby
Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (861)
"Everything was well!"
United States
Ahmed
The price is ฿3,070
฿3,407 total
includes taxes & fees
4 Jan - 5 Jan 2026
Comfort Inn & Suites Chestertown
Private beach nearby, sun-loungers, beach volleyball
The Lodge at Great Oak Landing

The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
3.5 star property
Chestertown
7.8 out of 10, Good, (77)
"Very nice rooms, "
United States
Stephania
The price is ฿3,114
฿3,561 total
includes taxes & fees
4 Jan - 5 Jan 2026
The Lodge at Great Oak Landing
Suite, Multiple Beds, Non Smoking | Desk, laptop workspace, blackout curtains, iron/ironing board
Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
2.0 star property
Chestertown
7.2 out of 10, Good, (424)
"Professional staff, warm greetings clean room "
United States
Dr. Nicholas and Mrs. Karen
The price is ฿2,265
฿2,514 total
includes taxes & fees
7 Jan - 8 Jan 2026
Red Roof Inn & Suites Chestertown
Exterior
Holiday Inn Express & Suites Middletown by IHG

Holiday Inn Express & Suites Middletown by IHG

Holiday Inn Express & Suites Middletown by IHG
2.5 star property
Middletown
9.2 out of 10, Wonderful, (653)
"Room was great the staff is so friendly every visit !!!!!"
United States
Dennis
The price is ฿2,831
฿3,143 total
includes taxes & fees
25 Jan - 26 Jan 2026
Holiday Inn Express & Suites Middletown by IHG
Restaurant
Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South
2.5 star property
Edgewood
9.2 out of 10, Wonderful, (1009)
"Awesome 2 night stay will be back❤️❤️"
United States
LaShawn
The price is ฿2,554
฿2,860 total
includes taxes & fees
6 Jan - 7 Jan 2026
Hampton Inn & Suites Edgewood/Aberdeen-South
Restaurant
Hampton Inn & Suites Baltimore/Aberdeen

Hampton Inn & Suites Baltimore/Aberdeen

Hampton Inn & Suites Baltimore/Aberdeen
2.5 star property
Aberdeen
9.0 out of 10, Wonderful, (607)
"very pet friendly!!"
United States
larry
The price is ฿3,086
฿3,457 total
includes taxes & fees
17 Jan - 18 Jan 2026
Hampton Inn & Suites Baltimore/Aberdeen
Terrace/patio
Home2 Suites by Hilton Baltimore / Aberdeen, MD

Home2 Suites by Hilton Baltimore / Aberdeen, MD

Home2 Suites by Hilton Baltimore / Aberdeen, MD
3.0 star property
Aberdeen
8.8 out of 10, Excellent, (340)
"Clean room, friendly staff"
United States
Julie
The price is ฿2,812
฿3,149 total
includes taxes & fees
29 Jan - 30 Jan 2026
Home2 Suites by Hilton Baltimore / Aberdeen, MD
Lobby lounge
Courtyard Aberdeen at Ripken Stadium

Courtyard Aberdeen at Ripken Stadium

Courtyard Aberdeen at Ripken Stadium
3.0 star property
Aberdeen
8.6 out of 10, Excellent, (219)
"We reserved 4 rooms, and arrived around noon. We didn't think, with early arrival, that our rooms would be ready, but they were! The staff was extremely accommodating and friendly. Our rooms were immaculate, beds comfy. It was a great stay for visiting family in the area. "
United States
Stephen
The price is ฿2,647
฿2,965 total
includes taxes & fees
25 Jan - 26 Jan 2026
Courtyard Aberdeen at Ripken Stadium
Exterior
Hilton Garden Inn Aberdeen

Hilton Garden Inn Aberdeen

Hilton Garden Inn Aberdeen
3.0 star property
Aberdeen
8.6 out of 10, Excellent, (635)
"High quality pillows Comfortable bed Clean room Kuerig Big room Strong WiFi Clean shower Good shampoo Excellent towels Plenty of drawers and closet space Comfy chair Great desk space"
United States
John
The price is ฿3,028
฿3,391 total
includes taxes & fees
7 Jan - 8 Jan 2026
Hilton Garden Inn Aberdeen
Exterior
Holiday Inn Belcamp - Aberdeen Area by IHG

Holiday Inn Belcamp - Aberdeen Area by IHG

Holiday Inn Belcamp - Aberdeen Area by IHG
3.0 star property
Belcamp
8.4 out of 10, Very good, (741)
"the room was spotless and the breakfast was very nice."
United States
Carl
The price is ฿2,234
฿2,502 total
includes taxes & fees
4 Jan - 5 Jan 2026
Holiday Inn Belcamp - Aberdeen Area by IHG
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.
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Top Chestertown Hotel Reviews

Frequently asked questions

Searching for an LGBTQ-friendly hotel in Chestertown?
Whether you are travelling with your partner or flying solo, you'll find Chestertown hotels that are members of the International Gay & Lesbian Travel Association on Expedia. Discover the people, places and traditions found only in Chestertown.
What is the top LGBTQ-friendly place to stay in Chestertown?
Comfort Inn & Suites Chestertown is a top LGBTQ-friendly hotel, and features free breakfast and free WiFi. Red Roof Inn & Suites Chestertown and The Lodge at Great Oak Landing are other good options for your stay.
How many LGBTQ-friendly hotels will I find in Chestertown?
There are currently 3 LGBTQ-friendly hotels in Chestertown.
What should I do while I'm visiting Chestertown?
During your trip, get out and enjoy everything Chestertown has to offer. You and your travelling companions may want to visit Historical Society of Kent County Maryland, Northern Chesapeake Bay and Chesapeake Bay. While you're here, create some great memories of your trip with stops at Chestertown Historic District, Rolphs Wharf Marina and Crumpton Auction.
What is a gay-friendly hotel in Chestertown?
LGBTQ-friendly hotels are places where lesbian, gay, bisexual and transgender travellers 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 Chestertown, hotels affiliated with IGLTA prioritise a diverse environment in which guests are welcomed, respected and not obliged to declare or hide their sexual orientation.
What can I expect from LGBTQ-friendly accommodation in Chestertown?
Take a holiday from the ordinary; stay at a gay-friendly hotel in Chestertown, and the staff will help you explore the local gay scene and the LGBTQ+ culture. Many of our LGBTQ-friendly accommodation options offer community-specific packages, exclusive tours and opportunities for social interaction.