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

Gay friendly Hotels in Chestertown, Maryland

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Check availability on Chestertown Gay friendly Hotels

Tonight
Sep 29 - Sep 30
Tomorrow
Sep 30 - Oct 1
This weekend
Oct 2 - Oct 4
Next weekend
Oct 9 - Oct 11

Our top choices for Chestertown LGBT-friendly hotels

A modern dining area with a central island, multiple tables, and chairs. There are signs for 'RISP' and 'SILVER' on the wall, and an 'EXIT' sign above a door.
A brick wall with a sign stating "Washington College Founded 1782" and a tree above it.
A hotel room with two beds, a desk, a TV, and a window with curtains.
A modern lounge area with seating, a fireplace, and a television.

1. Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
Chestertown
United States
Amy
P6,487
P7,201 total
includes taxes & fees
Oct 25 - Oct 26
Comfort Inn & Suites Chestertown
A multi-story brick building with a covered entrance and a parking lot.
A spacious living room with a fireplace, a stone accent wall, and a television mounted above it.
A hotel sign with a red background and white lettering, a parking lot, and a building with a brick facade.
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
Linda
P4,503
P4,998 total
includes taxes & fees
Oct 6 - Oct 7
Red Roof Inn & Suites Chestertown
A lakeside picnic area with wooden benches and picnic tables, surrounded by trees and a clear sky.
A spacious room with a large window, a seating area with a sofa and armchairs, a small table with a plant, and a display of various items including a mannequin and shelves with products.
A campfire in a stone fire pit by a lakeside at sunset.
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
Sandra
P6,755
P7,723 total
includes taxes & fees
Oct 1 - Oct 2
The Lodge at Great Oak Landing
Two Adirondack chairs facing a calm body of water with a clear sky above.
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 Holiday Inn Express building with a brick facade, illuminated signage, and a parking lot with SUVs.
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
P6,880
P7,637 total
includes taxes & fees
Oct 25 - Oct 26
Holiday Inn Express Annapolis East-Kent Island by IHG
A patio with outdoor seating, overlooking a marina with boats.
An indoor swimming pool with clear views of boats and water.
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.

5. Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
Grasonville
United States
roney
P9,180
P10,190 total
includes taxes & fees
Oct 6 - Oct 7
Hilton Garden Inn Kent Island Marina
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 reception area with a wooden reception desk, a coffee station, and framed pictures on the wall.
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
United States
Lyn
P5,590
P6,261 total
includes taxes & fees
Oct 12 - Oct 13
Hampton Inn & Suites Edgewood/Aberdeen-South
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.
An indoor swimming pool with clear depth markers, lounge chairs, and umbrellas.
A modern restaurant with a bar area, seating, and a counter with a menu display.

7. Home2 Suites by Hilton Baltimore / Aberdeen, MD

Home2 Suites by Hilton Baltimore / Aberdeen, MD
Aberdeen
United States
Adam
P6,616
P7,410 total
includes taxes & fees
Oct 18 - Oct 19
Home2 Suites by Hilton Baltimore / Aberdeen, MD
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 room with two beds, a bathroom, and a seating area.

8. SpringHill Suites Baltimore White Marsh/Middle River

SpringHill Suites Baltimore White Marsh/Middle River
Middle River
United States
Evelyn
P6,698
P7,737 total
includes taxes & fees
Oct 4 - Oct 5
SpringHill Suites Baltimore White Marsh/Middle River
A bar area with a marble countertop, bar stools, and shelves stocked with bottles.
A reception area with a wooden reception desk, a wall-mounted TV, and a refrigerator with beverages.
A brick building with a green awning labeled "Courtyard Marriott."
A modern living room with a fireplace, sofas, and a flat-screen TV.

9. Courtyard by Marriott Aberdeen at Ripken Stadium

Courtyard by Marriott Aberdeen at Ripken Stadium
Aberdeen
United States
Mike
P6,326
P7,085 total
includes taxes & fees
Oct 18 - Oct 19
Courtyard by Marriott Aberdeen at Ripken Stadium
A modern lobby with a curved sofa, red armchairs, a fireplace, and a dining area with green chairs.
A hotel room with a dining area, a TV, a dresser, and a tray table.
A hotel dining area with a buffet setup, multiple dining tables, chairs, and a ceiling fan.
An indoor swimming pool with lounge chairs and a hot tub, surrounded by large windows.

10. Homewood Suites by Hilton Bel Air

Homewood Suites by Hilton Bel Air
Bel Air
United States
Jennifer
P6,629
P7,425 total
includes taxes & fees
Oct 28 - Oct 29
Homewood Suites by Hilton Bel Air
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Top Chestertown Hotel Reviews

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?
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 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, 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, 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.

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