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
15 Oct - 16 Oct
Tomorrow
16 Oct - 17 Oct
This weekend
16 Oct - 18 Oct
Next weekend
23 Oct - 25 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 Comfort Inn & Suites hotel with a brick facade, arched entryway, and a well-maintained lawn.
A hotel room with two beds, a desk, a flat-screen TV, and a window with curtains.
A spacious dining area with multiple tables and chairs, a central island, and a kitchen in the background.

1. Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
Chestertown
United States
Amy
Rp1.746.617
Rp1.938.745 total
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 multi-story brick building with a covered entrance and a parking lot.
A living room with a fireplace, a television, and a stone accent wall.
A hotel sign with a red background and white lettering, a parking lot, and a building with a brick facade.

2. Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
Chestertown
United States
Kate
Rp1.288.639
Rp1.430.388 total
includes taxes & fees
27 Oct - 28 Oct
Red Roof Inn & Suites Chestertown
A lakeside picnic area with wooden benches and picnic tables, surrounded by trees and a clear sky.
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.
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.

3. The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
Chestertown
United States
Sandra
Rp1.933.200
Rp2.210.227 total
includes taxes & fees
19 Oct - 20 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 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.

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

Holiday Inn Express Annapolis East-Kent Island by IHG
Grasonville
United States
Marc
Rp1.772.397
Rp1.967.361 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.
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 modern lobby with a bar area, seating arrangements, and a television screen.

5. SpringHill Suites Baltimore White Marsh/Middle River

SpringHill Suites Baltimore White Marsh/Middle River
Middle River
United States
Juanita
Rp1.917.411
Rp2.214.609 total
includes taxes & fees
22 Oct - 23 Oct
SpringHill Suites Baltimore White Marsh/Middle River
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 coffee shop interior with a counter, shelves stocked with snacks, and a refrigerated display.
A modern building with a stone facade, large windows, and outdoor seating area with chairs.

6. Hilton Garden Inn Bel Air

Hilton Garden Inn Bel Air
Bel Air
United States
Jaccilynne
Rp1.886.976
Rp2.113.414 total
includes taxes & fees
1 Nov - 2 Nov
Hilton Garden Inn Bel Air
A modern hotel lobby with a long dining table, several chairs, and a bar area.
A hotel pool area with a clear pool, lounge chairs, and a seating area with tables and chairs.
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.

7. Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South
Edgewood
United States
Regina
Rp1.526.768
Rp1.709.980 total
includes taxes & fees
1 Nov - 2 Nov
Hampton Inn & Suites Edgewood/Aberdeen-South
A Victorian-style building with a porch, outdoor seating, and a sign for Vandiver Inn.
A traditional house with a covered porch, white picket fence, and lush greenery.
A bedroom with a four-poster bed, a fireplace, a mirror, and a stained glass window.
A cozy living room with a sofa, armchair, and a fireplace.

8. Vandiver Inn

Vandiver Inn
Havre De Grace
United States
Mary
Rp3.128.920
Rp3.504.390 total
includes taxes & fees
19 Oct - 20 Oct
Vandiver Inn
A patio with outdoor seating, overlooking a marina with boats.
An indoor swimming pool with clear views of boats and water.
A waterfront hotel with multiple balconies, a marina with yachts, and a well-lit exterior.
A marina with multiple boats docked, a Hilton Garden Inn hotel, and a parking area.

9. Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
Grasonville
United States
Charles
Rp2.627.802
Rp2.916.860 total
includes taxes & fees
25 Oct - 26 Oct
Hilton Garden Inn Kent Island Marina
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 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 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.

10. Home2 Suites by Hilton Baltimore / Aberdeen, MD

Home2 Suites by Hilton Baltimore / Aberdeen, MD
Aberdeen
United States
Kenley
Rp1.746.975
Rp1.956.613 total
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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