Chestertown Gay friendly Hotels

  • 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 Chestertown Gay friendly Hotels

Our top choices for Chestertown LGBT-friendly hotels

Private beach nearby, sun-loungers, beach volleyball

The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
3.5 star property
Chestertown
8.0 out of 10, Very good, (82 reviews)
"clean, comfortable, and staff was friendly and helpful. "
United States
Gail
The price is RM523
RM598 total
includes taxes & fees
28 May - 29 May
The Lodge at Great Oak Landing
Exterior

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (911 reviews)
"Great visit"
United States
Danielle
The price is RM440
RM489 total
includes taxes & fees
15 Jun - 16 Jun
Comfort Inn & Suites Chestertown
Lobby lounge

Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
2.0 star property
Chestertown
7.2 out of 10, Good, (440 reviews)
"Nothing special but good for the price. "
United States
Andreas
The price is RM285
RM316 total
includes taxes & fees
1 Jun - 2 Jun
Red Roof Inn & Suites Chestertown
Exterior detail

Vandiver Inn

Vandiver Inn
3.5 star property
Havre De Grace
9.4 out of 10, Exceptional, (544 reviews)
"Breakfast menu was very good, staff friendly and helpful. "
United States
JoEllen
The price is RM571
RM640 total
includes taxes & fees
19 May - 20 May
Vandiver Inn
Lobby

Hampton Inn & Suites Baltimore/Aberdeen

Hampton Inn & Suites Baltimore/Aberdeen
2.5 star property
Aberdeen
9.0 out of 10, Wonderful, (651 reviews)
"Clean, comfortable, decent breakfast."
United States
Diane
The price is RM373
RM418 total
includes taxes & fees
25 May - 26 May
Hampton Inn & Suites Baltimore/Aberdeen
Terrace/patio

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, (378 reviews)
"Great stay at this"
United States
Wilson
The price is RM386
RM432 total
includes taxes & fees
25 May - 26 May
Home2 Suites by Hilton Baltimore / Aberdeen, MD
Lobby lounge

Flag House Inn

Flag House Inn
3.5 star property
Historic District
9.2 out of 10, Wonderful, (94 reviews)
"Great location. Beautiful room and exemplary service. "
United States
Nathan
The price is RM923
RM1,052 total
includes taxes & fees
25 May - 26 May
Flag House Inn
Terrace/patio

Fairfield Inn & Suites by Marriott Aberdeen

Fairfield Inn & Suites by Marriott Aberdeen
3.0 star property
Aberdeen
9.0 out of 10, Wonderful, (339 reviews)
"The staff was lovely and so accommodating. Definitely the best part of our stay."
United States
Maritza
The price is RM433
RM485 total
includes taxes & fees
8 Jun - 9 Jun
Fairfield Inn & Suites by Marriott Aberdeen
Reception

Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South
2.5 star property
Edgewood
9.4 out of 10, Exceptional, (1,004 reviews)
"Best place to stay"
United States
Victor
The price is RM337
RM378 total
includes taxes & fees
26 May - 27 May
Hampton Inn & Suites Edgewood/Aberdeen-South
In-room safe, desk, blackout curtains, free WiFi

Red Roof Inn Aberdeen

Red Roof Inn Aberdeen
2.0 star property
Aberdeen
6.4 out of 10, (1,003 reviews)
"Property was ok. Room was ok definitely needs major update and paint. Needs new bed. Smelt like cig smoke for manys years. Everthing atain yellow. Look like alot of permant residents. In back building kind of like being in the projects."
United States
Sheena
The price is RM217
RM244 total
includes taxes & fees
19 May - 20 May
Red Roof Inn Aberdeen
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 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 Rolphs Wharf Marina, Northern Chesapeake Bay and Chesapeake Bay. While you're here, create some great memories of your trip with stops at Historical Society of Kent County Maryland, Garfield Center for the Arts at the Prince Theater and Chestertown Historic District.
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.

Explore a world of travel with Expedia