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

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Check availability on Chestertown Gay-Friendly Hotels

Tonight
25 Oct - 26 Oct
Tomorrow
26 Oct - 27 Oct
Next weekend
30 Oct - 1 Nov
In two weeks
6 Nov - 8 Nov

Our top choices for Chestertown LGBT-friendly hotels

A hotel lobby with a fireplace, seating area, and a television.
A spacious dining area with multiple tables and chairs, a central island, and a kitchen in the background.
A hotel room with a bed, a sofa, a dining table, and a small round table.
A brick wall with a sign stating "Washington College Founded 1782" and a tree above it.

1. Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
Chestertown
United States
Roberta
฿3,317
฿3,682 total
includes taxes & fees
15 Nov - 16 Nov
Comfort Inn & Suites Chestertown
A spacious living room with a fireplace, a stone accent wall, and a television mounted above it.
A hotel entrance with a clear sky, a parking lot, and a brick building with a covered entrance.
A hotel room with a bed, a couch, a painting, and a window with curtains.
A living room with a fireplace, a television, and a stone accent wall.

2. Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
Chestertown
United States
Mary
฿2,431
฿2,698 total
includes taxes & fees
1 Nov - 2 Nov
Red Roof Inn & Suites Chestertown
A campfire in a stone fire pit by a lakeside at sunset.
A marina with docked boats, a wooden walkway with railings, and a sign indicating 'D DOCK'.
A lakeside picnic area with wooden benches and picnic tables, surrounded by trees and a clear sky.
A large brick building with a symmetrical facade, multiple chimneys, and a central entrance.

3. The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
Chestertown
United States
Steve allen
฿3,647
฿4,169 total
includes taxes & fees
27 Oct - 28 Oct
The Lodge at Great Oak Landing
A gazebo with a view of a lake at dusk.
A hotel room with a large bed, a desk with a flat-screen TV, a chair, a small table with a lamp, and a window with curtains.
A reception desk with a modern design, a digital display, and a check-in counter.
A Holiday Inn Express building with a brick facade, illuminated signage, and a parking lot with SUVs.

4. Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG
Grasonville
United States
Michelle
฿3,343
฿3,710 total
includes taxes & fees
22 Nov - 23 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.
An outdoor patio with brick walls, green chairs, and a fire pit.
A modern lobby with a bar area, seating arrangements, and a television screen.
A hotel with a modern facade, a covered entrance, and a red car parked outside.

5. SpringHill Suites Baltimore White Marsh/Middle River

SpringHill Suites Baltimore White Marsh/Middle River
Middle River
United States
Soma
฿3,616
฿4,177 total
includes taxes & fees
29 Oct - 30 Oct
SpringHill Suites Baltimore White Marsh/Middle River
A modern hotel lobby with a long dining table, several chairs, and a bar area.
A hotel room with a kitchenette, a large mirror, a window with curtains, a desk, and a chair.
A hotel pool area with a clear pool, lounge chairs, and a seating area with tables and chairs.
A hotel reception area with a wooden reception desk, a coffee station, and framed pictures on the wall.

6. Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South
Edgewood
United States
Thomas
฿2,879
฿3,225 total
includes taxes & fees
1 Nov - 2 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.
A modern hotel with a stone facade, a clear entrance canopy, and a prominent Hilton Inn sign.
A modern building with a stone facade, large windows, and outdoor seating area with chairs.
A modern coffee shop interior with a counter, shelves stocked with snacks, and a refrigerated display.

7. Hilton Garden Inn Bel Air

Hilton Garden Inn Bel Air
Bel Air
United States
Jaccilynne
฿3,559
฿3,986 total
includes taxes & fees
1 Nov - 2 Nov
Hilton Garden Inn Bel Air
A balcony with a view of a body of water, a row of buildings, and a chair.
A spacious dining area with a large rectangular table, multiple chairs, and a chandelier.
A marina with multiple boats docked, a Hilton Garden Inn hotel, and a parking area.
An indoor swimming pool with clear views of boats and water.

8. Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
Grasonville
United States
Charles
฿4,368
฿4,848 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.
A formal dining room with a long table, chairs, a chandelier, and a fireplace.
A bedroom with a four-poster bed, a fireplace, a mirror, and a stained glass window.
A traditional house with a covered porch, white picket fence, and lush greenery.

9. Vandiver Inn

Vandiver Inn
Havre De Grace
United States
Mary
฿5,902
฿6,610 total
includes taxes & fees
26 Oct - 27 Oct
Vandiver Inn
An outdoor patio with a stone fire pit, wicker furniture, and a view of the interior.
A multi-story hotel with a modern facade, featuring a prominent 'HOME 2' sign. The entrance is accessible via a covered walkway, and the building is equipped with large windows and a flagpole.
A modern restaurant with a bar area, seating, and a counter with a menu display.
An indoor swimming pool with clear depth markers, lounge chairs, and umbrellas.

10. Home2 Suites by Hilton Baltimore / Aberdeen, MD

Home2 Suites by Hilton Baltimore / Aberdeen, MD
Aberdeen
United States
Kenley
฿3,295
฿3,690 total
includes taxes & fees
22 Nov - 23 Nov
Home2 Suites by Hilton Baltimore / Aberdeen, MD
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.

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