Photo by Assya A

Find Gay friendly Hotels in Chestertown, MD

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 Gay friendly Hotels

Top Chestertown Gay 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
7.8 out of 10, Good, (70)
"Everything was perfect. The staff is super friendly, the room was clean and fresh. The beds were super comfy, the food is amazing and the chef was super nice!! Great friendly atmosphere. I’m definitely going back!!"
The price is NT$4,043
NT$4,623 total
includes taxes & fees
Oct 19 - Oct 20
The Lodge at Great Oak Landing
Lobby
Comfort Inn & Suites Chestertown
Comfort Inn & Suites Chestertown
2.5 star property
8.6 out of 10, Excellent, (829)
"The thermostat controls were easy to adjust. Night desk lady was friendly and pleasant. "
The price is NT$3,117
NT$3,460 total
includes taxes & fees
Oct 19 - Oct 20
Comfort Inn & Suites Chestertown
Suite, Multiple Beds, Non Smoking | 1 bedroom, desk, laptop workspace, blackout drapes
Red Roof Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
2.0 star property
7.2 out of 10, Good, (406)
"We had a great stay with our two Pups.. The room was very nice and comfortable and very clean."
The price is NT$2,475
NT$2,747 total
includes taxes & fees
Oct 27 - Oct 28
Red Roof Inn & Suites Chestertown
Restaurant
Hampton Inn & Suites Baltimore/Aberdeen
Hampton Inn & Suites Baltimore/Aberdeen
2.5 star property
9.0 out of 10, Wonderful, (584)
"This Hotel was excellent in all ways. "
The price is NT$2,989
NT$3,348 total
includes taxes & fees
Nov 2 - Nov 3
Hampton Inn & Suites Baltimore/Aberdeen
Exterior
Holiday Inn Express & Suites Middletown by IHG
Holiday Inn Express & Suites Middletown by IHG
2.5 star property
9.2 out of 10, Wonderful, (629)
"This was a great relaxing stay"
The price is NT$3,154
NT$3,501 total
includes taxes & fees
Nov 2 - Nov 3
Holiday Inn Express & Suites Middletown by IHG
Exterior
Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
2.5 star property
9.0 out of 10, Wonderful, (528)
"Super clean, a great place to stay"
The price is NT$2,542
NT$2,848 total
includes taxes & fees
Oct 22 - Oct 23
Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
Restaurant
Hampton Inn & Suites Edgewood/Aberdeen-South
Hampton Inn & Suites Edgewood/Aberdeen-South
2.5 star property
9.4 out of 10, Exceptional, (1006)
"Love love love this hotel they provided me with excellent care. Also helped me out with late checkout as needed. Great stay booking again very soon "
The price is NT$2,606
NT$2,919 total
includes taxes & fees
Oct 23 - Oct 24
Hampton Inn & Suites Edgewood/Aberdeen-South
Reception
Hampton Inn Middletown
Hampton Inn Middletown
2.5 star property
8.8 out of 10, Excellent, (842)
"Enjoyed the amenities and great location for shops nearby "
The price is NT$3,107
NT$3,449 total
includes taxes & fees
Nov 4 - Nov 5
Hampton Inn Middletown
Free daily buffet breakfast
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
3.0 star property
7.0 out of 10, Good, (1025)
"Had a nice stay "
The price is NT$2,377
NT$2,745 total
includes taxes & fees
Oct 26 - Oct 27
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh
Terrace/patio
Historic Inns of Annapolis
Historic Inns of Annapolis
3.5 star property
9.0 out of 10, Wonderful, (1861)
"The hotel was absolutely clean and close to the shops and restaurants. "
Historic Inns of Annapolis
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

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 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, 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.