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

  • 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 prices for these dates

Tonight
14 Nov - 15 Nov
Tomorrow
15 Nov - 16 Nov
Next weekend
20 Nov - 22 Nov
In two weeks
27 Nov - 29 Nov

Our top choices for Chestertown LGBT-friendly hotels

A hotel lobby with a fireplace, seating area, and a television.

1. Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (1,000 reviews)
"The front desk staff were so nice, room very clean."
United States
John
The price is €97
includes taxes & fees
6 Dec - 7 Dec
Comfort Inn & Suites Chestertown
A living room with a fireplace, a television, and a stone accent wall.

2. Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
2.0 star property
Chestertown
7.2 out of 10, Good, (514 reviews)
"Nice clean place and priced good. Plenty of mirrors, plenty of counter space, many tv channels even Christian based ones and comfortable bed. The room needs up dating since damage area on ceiling and corner location rug worn spot. I felt safe as a solo, could check in late and close to historic Chestertown. I would come again."
United States
Regina
The price is €72
includes taxes & fees
15 Dec - 16 Dec
Red Roof Inn & Suites Chestertown
A lakeside picnic area with wooden benches and picnic tables, surrounded by trees and a clear sky.

3. The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
3.5 star property
Chestertown
8.0 out of 10, Very good, (130 reviews)
"Great place! Clean, comfortable and in a beautiful area. I won’t stay anywhere else when I’m in that area."
United States
William
The price is €112
includes taxes & fees
23 Nov - 24 Nov
The Lodge at Great Oak Landing
Two Adirondack chairs facing a calm body of water with a clear sky above.

4. 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, (1,002 reviews)
"Helpful staff, nice location on the river"
United States
Suzanne
The price is €96
includes taxes & fees
13 Dec - 14 Dec
Holiday Inn Express Annapolis East-Kent Island by IHG
A modern restaurant with high ceilings, pendant lighting, and a mix of seating options including tables and booths.

5. Hilton Garden Inn Bel Air

Hilton Garden Inn Bel Air
3.0 star property
Bel Air
9.4 out of 10, Exceptional, (316 reviews)
"The whole experience was great 👍"
United States
Donald
The price is €103
includes taxes & fees
3 Dec - 4 Dec
Hilton Garden Inn Bel Air
A modern hotel lobby with a long dining table, several chairs, and a bar area.

6. Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South
2.5 star property
Edgewood
9.4 out of 10, Exceptional, (1,001 reviews)
"Very nice stay and staff"
United States
Deborah
The price is €86
includes taxes & fees
22 Nov - 23 Nov
Hampton Inn & Suites Edgewood/Aberdeen-South
A modern restaurant with high tables and chairs, a bar area, and a television screen displaying a news program.

7. SpringHill Suites Baltimore White Marsh/Middle River

SpringHill Suites Baltimore White Marsh/Middle River
2.5 star property
Middle River
9.0 out of 10, Wonderful, (984 reviews)
"Very well-kept hotel. Staff was very welcoming and nice location with restaurants across the street."
United States
Justin
The price is €112
includes taxes & fees
19 Nov - 20 Nov
SpringHill Suites Baltimore White Marsh/Middle River
A patio with outdoor seating, overlooking a marina with boats.

8. Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
3.0 star property
Grasonville
8.8 out of 10, Excellent, (1,001 reviews)
"Everything was fantastic"
United States
Gamil
The price is €123
includes taxes & fees
22 Nov - 23 Nov
Hilton Garden Inn Kent Island Marina
A spacious hotel lobby with a large seating area, a television, a fireplace, and a coffee station.

9. Hampton Inn & Suites Baltimore/Aberdeen

Hampton Inn & Suites Baltimore/Aberdeen
2.5 star property
Aberdeen
9.0 out of 10, Wonderful, (706 reviews)
"Very friendly and helpful staff. The room was clean and comfortable. Plenty of parking and convenient to the interstate."
United States
William
The price is €97
includes taxes & fees
13 Dec - 14 Dec
Hampton Inn & Suites Baltimore/Aberdeen
An outdoor patio with a stone fire pit, wicker furniture, and a view of the interior.

10. 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, (432 reviews)
"Would stay again"
United States
Kenley
The price is €99
includes taxes & fees
22 Nov - 23 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

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?

The Lodge at Great Oak Landing is a top LGBTQ-friendly lodge, and features a golf course and free WiFi. Comfort Inn & Suites Chestertown and Red Roof Inn & Suites Chestertown 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, Chestertown Historic District and Rolphs Wharf Marina. While you're here, create some great memories of your trip with stops at Northern Chesapeake Bay, Chesapeake Bay and Larrabee Arts Center.

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