Aerial summer view of colonial Chestertown on the Chesapeake Bay in Maryland USA

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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
3.0 star property
Chestertown
7.8 out of 10, Good, (87 reviews)
"This property is situated in a beautiful marina with excellent facilities. Guests staying at the Lodge can also enjoy complimentary golf, which was a great bonus. We thoroughly enjoyed our stay and would happily return. The only drawback was that the Wi-Fi service was somewhat inconsistent."
United States
Myrna
The price is €131
includes taxes & fees
15 Jun - 16 Jun
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, (455 reviews)
"Nothing special but good for the price. "
United States
Andreas
The price is €69
includes taxes & fees
18 Jun - 19 Jun
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, (921 reviews)
"Great visit"
United States
Danielle
The price is €103
includes taxes & fees
5 Jul - 6 Jul
Comfort Inn & Suites Chestertown
Exterior detail

Vandiver Inn

Vandiver Inn
3.5 star property
Havre De Grace
9.4 out of 10, Exceptional, (551 reviews)
"The staff was wonderful! the place was nice and clean. everything was in walking distance. highly recommend staying here if visiting."
United States
Danielle
The price is €140
includes taxes & fees
15 Jun - 16 Jun
Vandiver Inn
Meeting facility

Historic Inns of Annapolis

Historic Inns of Annapolis
3.5 star property
Historic District
9.0 out of 10, Wonderful, (1,873 reviews)
"Great hotel..will definitely be back"
United States
Randy
The price is €133
includes taxes & fees
5 Jul - 6 Jul
Historic Inns of Annapolis
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, (380 reviews)
"Great stay at this"
United States
Wilson
The price is €95
includes taxes & fees
22 Jun - 23 Jun
Home2 Suites by Hilton Baltimore / Aberdeen, MD
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, (344 reviews)
"Would definitely stay here again"
United States
Marie
The price is €106
includes taxes & fees
28 Jun - 29 Jun
Fairfield Inn & Suites by Marriott Aberdeen
Exterior

Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG
2.5 star property
Grasonville
9.2 out of 10, Wonderful, (1,001 reviews)
"Beautiful view!!! Clean hotel and very nice helpful staff. Would stay again."
United States
Michele
The price is €129
includes taxes & fees
6 Jul - 7 Jul
Holiday Inn Express Annapolis East-Kent Island by IHG
Reception

Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South
2.5 star property
Edgewood
9.4 out of 10, Exceptional, (1,015 reviews)
"Convenient location, clean room and delicious breakfast"
United States
Connie
The price is €97
includes taxes & fees
5 Jul - 6 Jul
Hampton Inn & Suites Edgewood/Aberdeen-South
Lobby

Hampton Inn & Suites Baltimore/Aberdeen

Hampton Inn & Suites Baltimore/Aberdeen
2.5 star property
Aberdeen
9.0 out of 10, Wonderful, (661 reviews)
"Clean, comfortable, decent breakfast."
United States
Diane
The price is €92
includes taxes & fees
24 Jun - 25 Jun
Hampton Inn & Suites Baltimore/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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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.
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 Chestertown Historic District, Rolphs Wharf Marina and Northern Chesapeake Bay. While you're here, create some great memories of your trip with stops at Chesapeake Bay, Historical Society of Kent County Maryland and Garfield Center for the Arts at the Prince Theater.
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.