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

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

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Check availability on Chestertown LGBT-Friendly Hotels

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

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 modern lounge area with seating, a fireplace, and a television.
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.

1. Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
Chestertown
United States
Amy
€101
includes taxes & fees
25 Oct - 26 Oct
Comfort Inn & Suites Chestertown
A multi-story brick building with a covered entrance and a parking lot.
A hotel room with a bed, a sofa, a desk, and a painting on the wall.
A living room with a fireplace, a television, and a stone accent wall.
A spacious living room with a fireplace, a stone accent wall, and a television mounted above it.

2. Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
Chestertown
United States
Linda
€70
includes taxes & fees
6 Oct - 7 Oct
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
€109
includes taxes & fees
1 Oct - 2 Oct
The Lodge at Great Oak Landing
Two Adirondack chairs facing a calm body of water with a clear sky above.
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.
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.

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

Holiday Inn Express Annapolis East-Kent Island by IHG
Grasonville
United States
Marc
€107
includes taxes & fees
25 Oct - 26 Oct
Holiday Inn Express Annapolis East-Kent Island by IHG
A patio with outdoor seating, overlooking a marina with boats.
A marina with multiple boats docked, a Hilton Garden Inn hotel, and a parking area.
A waterfront hotel with multiple balconies, a marina with yachts, and a well-lit exterior.
A spacious dining area with a large rectangular table, multiple chairs, and a chandelier.

5. Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
Grasonville
United States
roney
€143
includes taxes & fees
12 Oct - 13 Oct
Hilton Garden Inn Kent Island Marina
A modern hotel lobby with a long dining table, several chairs, and a bar area.
A hotel reception area with a wooden reception desk, a coffee station, and framed pictures on the wall.
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
United States
Lyn
€88
includes taxes & fees
12 Oct - 13 Oct
Hampton Inn & Suites Edgewood/Aberdeen-South
An outdoor patio with a stone fire pit, wicker furniture, and a view of the interior.
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.
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.

7. Home2 Suites by Hilton Baltimore / Aberdeen, MD

Home2 Suites by Hilton Baltimore / Aberdeen, MD
Aberdeen
United States
Adam
€104
includes taxes & fees
18 Oct - 19 Oct
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.
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.
An outdoor patio with brick walls, green chairs, and a fire pit.

8. SpringHill Suites Baltimore White Marsh/Middle River

SpringHill Suites Baltimore White Marsh/Middle River
Middle River
United States
Evelyn
€109
includes taxes & fees
4 Oct - 5 Oct
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 modern living room with a fireplace, sofas, and a flat-screen TV.
A brick building with a green awning labeled "Courtyard Marriott."

9. Courtyard by Marriott Aberdeen at Ripken Stadium

Courtyard by Marriott Aberdeen at Ripken Stadium
Aberdeen
United States
Mike
€100
includes taxes & fees
18 Oct - 19 Oct
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 outdoor patio with round tables and chairs, a barbecue grill, and umbrellas providing shade.

10. Homewood Suites by Hilton Bel Air

Homewood Suites by Hilton Bel Air
Bel Air
United States
Jennifer
€108
includes taxes & fees
14 Oct - 15 Oct
Homewood Suites by Hilton Bel Air
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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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