Find Gay friendly Hotels in Chestertown, MD

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
7.8 out of 10, Good, (77 reviews)
"Very nice rooms, "
United States
Stephania
The Lodge at Great Oak Landing
Lobby lounge

Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
2.0 star property
Chestertown
7.2 out of 10, Good, (434 reviews)
"Arrived earlier than expected and the staff was very accommodating and friendly which made for an excellent stay from start to finish. "
United States
Linette
Red Roof Inn & Suites Chestertown
Free daily full breakfast

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (896 reviews)
"Best place to stay always "
United States
Robert
Comfort Inn & Suites Chestertown
Lobby lounge

Flag House Inn

Flag House Inn
3.5 star property
Historic District
9.2 out of 10, Wonderful, (92 reviews)
"The room was over the garage. You couldn’t stand up in half the room as the ceiling was too low. Multiple tripping areas walking into and out of the space. No heat in bathroom. You have to walk to the front of house to enter for coffee in the morning. They have the nerve to charge you to park at the house. "
United States
Richard
Flag House Inn
Exterior detail

Vandiver Inn

Vandiver Inn
3.5 star property
Havre De Grace
9.4 out of 10, Exceptional, (538 reviews)
"As always we loved our stay! Definitely will be coming back "
United States
John
Vandiver Inn
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, (361 reviews)
"Staff was very friendly and it was a perfect location for us"
United States
Ryan
Home2 Suites by Hilton Baltimore / Aberdeen, MD
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, (674 reviews)
"Great location and nice place to stay. Walk to nearby things to do and enjoy. "
United States
Sharon
Holiday Inn Express & Suites Middletown by IHG
Reception

Hilton Garden Inn Aberdeen

Hilton Garden Inn Aberdeen
3.0 star property
Aberdeen
8.6 out of 10, Excellent, (647 reviews)
"Quiet, clean, and friendly staff."
United States
William
Hilton Garden Inn 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, (1,008 reviews)
"Clean room, nice staff and great breakfast "
United States
Curtis
Hampton Inn & Suites Edgewood/Aberdeen-South
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, (327 reviews)
"The staff was lovely and so accommodating. Definitely the best part of our stay."
United States
Maritza
Fairfield Inn & Suites by Marriott 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.
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Frequently asked questions

Looking for a gay-friendly accommodation in Chestertown?
Whether you are traveling with your partner or flying solo, you'll find LGBTQ-friendly hotels in Chestertown on Expedia. Discover the people, places, and traditions found only in Chestertown.
What is the favorite LGBTQ-friendly accommodation 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 two other good choices for your stay.
How many gay-friendly hotels will I find in Chestertown?
There are currently 3 LGBTQ-friendly lodging options in Chestertown.
What should I do while I'm visiting Chestertown?
During your vacation, get out and enjoy everything Chestertown is known for. You and your traveling companions may want to visit Historical Society of Kent County Maryland, Rolphs Wharf Marina, and Northern Chesapeake Bay. While you're here, create some great memories of your trip with stops at Chesapeake Bay, Garfield Center for the Arts at the Prince Theater, and Chestertown Historic District.
What is a gay-friendly hotel in Chestertown?
LGBTQ-friendly hotels, also known as gay-friendly hotels, welcome all travelers who identify as LGBTQIA+. Expedia has compiled a selection of LGBTQ-friendly hotels worldwide. In Chestertown, these hotels 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 Chestertown?
Stay at an LGBTQ-friendly hotel in Chestertown and the staff will help you explore the local gay scene and the LGBTQ+ culture. Some of Expedia's LGBTQ-friendly hotels go the extra mile and offer wedding ceremonies and honeymoon packages for same-sex couples.