Photo by Patricia Knorr

Chestertown Hotel Guide - LGBT-Friendly Hotels in Chestertown, Maryland

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 Chestertown LGBT-Friendly Hotels

Tonight
8 Nov - 9 Nov
Tomorrow
9 Nov - 10 Nov
Next weekend
14 Nov - 16 Nov
In two weeks
21 Nov - 23 Nov

Top Chestertown LGBT-Friendly Hotels

Lobby
Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

2.5 star property
Chestertown
8.6 out of 10, Excellent, (841)
"This property is clean and welcoming. We were pleasantly surprised. Check in was easy, and the room was great. Breakfast was wonderful! Great place to stay."
United States
Paula
The price is €98
includes taxes & fees
11 Nov - 12 Nov
Comfort Inn & Suites Chestertown
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, (74)
"Very nice rooms, "
United States
Stephania
The price is €98
includes taxes & fees
9 Nov - 10 Nov
The Lodge at Great Oak Landing
Suite, Multiple Beds, Non Smoking
Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

2.0 star property
Chestertown
7.2 out of 10, Good, (410)
"Food stains on the carpets, spots throughout the carpets in commons and in rooms."
United States
Allen
The price is €69
includes taxes & fees
30 Nov - 1 Dec
Red Roof Inn & Suites Chestertown
Restaurant
Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South

2.5 star property
Edgewood
9.4 out of 10, Exceptional, (1000)
"Very good breakfast options Convenient parking Clean room Friendly staff"
United States
Alexander
The price is €79
includes taxes & fees
17 Nov - 18 Nov
Hampton Inn & Suites Edgewood/Aberdeen-South
Exterior
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, (637)
"This was a great relaxing stay"
United States
Pamela
The price is €100
includes taxes & fees
5 Dec - 6 Dec
Holiday Inn Express & Suites Middletown by IHG
Restaurant
Hampton Inn & Suites Baltimore/Aberdeen

Hampton Inn & Suites Baltimore/Aberdeen

2.5 star property
Aberdeen
9.0 out of 10, Wonderful, (588)
"Great stay!"
United States
Barbara
The price is €88
includes taxes & fees
23 Nov - 24 Nov
Hampton Inn & Suites Baltimore/Aberdeen
Lobby lounge
Courtyard Aberdeen at Ripken Stadium

Courtyard Aberdeen at Ripken Stadium

3.0 star property
Aberdeen
8.6 out of 10, Excellent, (214)
"The staff was very friendly, easy and quick check-in. I would chose thus hotel again, very quiet. "
United States
Donna
The price is €98
includes taxes & fees
9 Dec - 10 Dec
Courtyard Aberdeen at Ripken Stadium
Reception
Hilton Garden Inn Bel Air

Hilton Garden Inn Bel Air

3.0 star property
Bel Air
9.4 out of 10, Exceptional, (218)
"The staff was amazing"
United States
Kendra
The price is €92
includes taxes & fees
3 Dec - 4 Dec
Hilton Garden Inn Bel Air
Exterior
Hilton Garden Inn Aberdeen

Hilton Garden Inn Aberdeen

3.0 star property
Aberdeen
8.6 out of 10, Excellent, (629)
"Great Restaurant and Front Desk Customer Service Team "
United States
Dave
The price is €93
includes taxes & fees
17 Nov - 18 Nov
Hilton Garden Inn 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, (331)
"All of the staff was friendly and welcoming. The facility was clean and comfortable. "
United States
Karen
The price is €92
includes taxes & fees
16 Nov - 17 Nov
Home2 Suites by Hilton Baltimore / Aberdeen, MD
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

Explore a world of travel with Expedia

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, Rolphs Wharf Marina and Chesapeake Bay. While you're here, create some great memories of your trip with stops at Garfield Center for the Arts at the Prince Theater, Chestertown Historic District and Sumner Hall.
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.