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

Gay friendly Hotels in Chestertown

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Check availability on Chestertown Gay friendly Hotels

Tonight
9 Oct - 10 Oct
Tomorrow
10 Oct - 11 Oct
This weekend
9 Oct - 11 Oct
Next weekend
16 Oct - 18 Oct

Our top choices for Chestertown LGBT-friendly hotels

A rectangular swimming pool with a 3 FT depth marker, surrounded by lounge chairs and a small table.
A hotel room with a bed, a desk with a coffee maker, a TV, a chair, and a window with curtains.
A spacious dining area with multiple tables and chairs, a central island, and a kitchen in the background.
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
Amy
S$139
includes taxes & fees
8 Nov - 9 Nov
Comfort Inn & Suites Chestertown
A hotel room with a sofa, two beds, a painting, and a lamp.
A hotel sign with a red background and white lettering, a parking lot, and a building with a brick facade.
A multi-story brick building with a covered entrance and a parking lot.
A hotel room with a bed, two bedside lamps, a sofa, a small table, and a painting on the wall.

2. Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
Chestertown
United States
Kate
S$102
includes taxes & fees
20 Oct - 21 Oct
Red Roof Inn & Suites Chestertown
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.
A marina with docked boats, a wooden walkway with railings, and a sign indicating 'D DOCK'.
A campfire in a stone fire pit by a lakeside at sunset.

3. The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
Chestertown
United States
Sandra
S$158
includes taxes & fees
20 Oct - 21 Oct
The Lodge at Great Oak Landing
Two Adirondack chairs facing a calm body of water with a clear sky above.
A Holiday Inn Express building with a brick facade, illuminated signage, and a parking lot with SUVs.
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 modern food court with a central island, various food stations, and a yogurt display.

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

Holiday Inn Express Annapolis East-Kent Island by IHG
Grasonville
United States
Marc
S$141
includes taxes & fees
8 Nov - 9 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 hotel with a modern facade, a covered entrance, and a red car parked outside.
A hotel room with two beds, a bathroom, and a seating area.

5. SpringHill Suites Baltimore White Marsh/Middle River

SpringHill Suites Baltimore White Marsh/Middle River
Middle River
United States
Juanita
S$158
includes taxes & fees
18 Oct - 19 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 room with a bed, a chair, a bathtub, a framed picture, and a nightstand with a lamp.

6. Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South
Edgewood
S$122
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 coffee shop interior with a counter, shelves stocked with snacks, and a refrigerated display.
A hotel reception area with a wooden reception desk, a minibar, and a wall with a textured pattern.
A modern hotel with a stone facade, a clear entrance canopy, and a prominent Hilton Inn sign.

7. Hilton Garden Inn Bel Air

Hilton Garden Inn Bel Air
Bel Air
United States
Jaccilynne
S$157
includes taxes & fees
2 Nov - 3 Nov
Hilton Garden Inn Bel Air
A patio with outdoor seating, overlooking a marina with boats.
A spacious dining area with a large rectangular table, multiple chairs, and a chandelier.
An indoor swimming pool with clear views of boats and water.
A marina with multiple boats docked, a Hilton Garden Inn hotel, and a parking area.

8. Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
Grasonville
United States
Charles
S$197
includes taxes & fees
20 Oct - 21 Oct
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 cozy living room with a sofa, armchair, and a fireplace.
A bedroom with a four-poster bed, a fireplace, a mirror, and a stained glass window.

9. Vandiver Inn

Vandiver Inn
Havre De Grace
United States
Mary
S$251
includes taxes & fees
13 Oct - 14 Oct
Vandiver Inn
An outdoor patio with a stone fire pit, wicker furniture, and a view of the interior.
A hotel room with a desk, office chair, sofa, and a dining table with chairs. There is a window with blinds, a painting on the wall, and a door leading to another room.
A modern restaurant with a bar area, seating, and a counter with a menu display.
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.

10. Home2 Suites by Hilton Baltimore / Aberdeen, MD

Home2 Suites by Hilton Baltimore / Aberdeen, MD
Aberdeen
United States
Kenley
S$140
includes taxes & fees
1 Nov - 2 Nov
Home2 Suites by Hilton Baltimore / Aberdeen, MD
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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.
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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