An aerial view of a town with a river, buildings, and surrounding greenery.

Search Gay-Friendly Hotels in Chestertown

  • 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

This weekend
30 Oct - 1 Nov
Next weekend
6 Nov - 8 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, (997 reviews)
"Good hotel"
United States
Michael
The price is Rp1.785.209
Rp1.981.583 total
includes taxes & fees
18 Nov - 19 Nov
Comfort Inn & Suites Chestertown
A lakeside picnic area with wooden benches and picnic tables, surrounded by trees and a clear sky.

2. The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
3.5 star property
Chestertown
8.0 out of 10, Very good, (124 reviews)
"Nice restairant and bar"
United States
Steve allen
The price is Rp1.952.640
Rp2.232.454 total
includes taxes & fees
2 Nov - 3 Nov
The Lodge at Great Oak Landing
A living room with a fireplace, a television, and a stone accent wall.

3. Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
2.0 star property
Chestertown
7.2 out of 10, Good, (511 reviews)
"Friendly staff, plenty of parking spaces,family friendly. The building is old but would do some renovation. Furniture needs replacement."
United States
Mary
The price is Rp1.305.557
Rp1.449.168 total
includes taxes & fees
3 Nov - 4 Nov
Red Roof Inn & Suites Chestertown
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, (1,000 reviews)
"A wonderful stay! Already planning a trip for next year!"
United States
Michelle
The price is Rp1.904.175
Rp2.113.633 total
includes taxes & fees
15 Nov - 16 Nov
Holiday Inn Express Annapolis East-Kent Island by IHG
A modern restaurant with high tables and chairs, a bar area, and a television screen displaying a news program.

5. 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, (968 reviews)
"The property was in a very nice area. There were a few restaurants near. Very quiet, will definitely stay again."
United States
Rashawna
The price is Rp1.942.259
Rp2.243.308 total
includes taxes & fees
1 Nov - 2 Nov
SpringHill Suites Baltimore White Marsh/Middle River
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, (1,007 reviews)
"Just like always a nice quiet place to stay"
United States
Thomas
The price is Rp1.546.553
Rp1.732.139 total
includes taxes & fees
22 Nov - 23 Nov
Hampton Inn & Suites Edgewood/Aberdeen-South
A modern restaurant with high ceilings, pendant lighting, and a mix of seating options including tables and booths.

7. Hilton Garden Inn Bel Air

Hilton Garden Inn Bel Air
3.0 star property
Bel Air
9.2 out of 10, Wonderful, (312 reviews)
"Lovely place! Friendly staff"
United States
Jaccilynne
The price is Rp1.957.673
Rp2.192.595 total
includes taxes & fees
22 Nov - 23 Nov
Hilton Garden Inn Bel Air
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
9.0 out of 10, Wonderful, (1,000 reviews)
"Great bartender she was a true professional at her job"
United States
Charles
The price is Rp2.377.499
Rp2.639.024 total
includes taxes & fees
22 Nov - 23 Nov
Hilton Garden Inn Kent Island Marina
A Victorian-style building with a porch, outdoor seating, and a sign for Vandiver Inn.

9. Vandiver Inn

Vandiver Inn
3.5 star property
Havre De Grace
9.4 out of 10, Exceptional, (577 reviews)
"A wonderful two nights at the Vandiver Inn! Beds were very comfortable, our room was spacious and the breakfast was outstanding!! I look forward to returning!!"
United States
Mary
The price is Rp3.169.998
Rp3.550.398 total
includes taxes & fees
2 Nov - 3 Nov
Vandiver Inn
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, (430 reviews)
"Would stay again"
United States
Kenley
The price is Rp1.769.613
Rp1.981.965 total
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

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.
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.