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

LGBT Welcoming Hotels & Resorts in Chestertown from NZ$140

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Check availability on Chestertown LGBT Welcoming Hotels

Tonight
24 Sept - 25 Sept
Tomorrow
25 Sept - 26 Sept
This weekend
25 Sept - 27 Sept
Next weekend
2 Oct - 4 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 hotel room with two beds, a desk, a TV, and a window with curtains.
A hotel reception area with a modern design, featuring a reception desk, a seating area, and a hallway leading to other rooms.

1. Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
Chestertown
United States
Amy
NZ$202
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 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.
A hotel room with a bed, a sofa, a desk, and a painting on the wall.

2. Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
Chestertown
United States
Linda
NZ$140
includes taxes & fees
5 Oct - 6 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 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
Jane
NZ$216
includes taxes & fees
7 Oct - 8 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 reception desk with a modern design, a digital display, and a check-in counter.

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

Holiday Inn Express Annapolis East-Kent Island by IHG
Grasonville
United States
Marc
NZ$201
includes taxes & fees
25 Oct - 26 Oct
Holiday Inn Express Annapolis East-Kent Island by IHG
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 room with a bed, a chair, a bathtub, a framed picture, and a nightstand with a lamp.
A hotel reception area with a wooden reception desk, a coffee station, and framed pictures on the wall.

5. Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South
Edgewood
United States
walter
NZ$167
includes taxes & fees
1 Oct - 2 Oct
Hampton Inn & Suites Edgewood/Aberdeen-South
A patio with outdoor seating, overlooking a marina with boats.
A waterfront hotel with multiple balconies, a marina with yachts, and a well-lit exterior.
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.

6. Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
Grasonville
United States
roney
NZ$284
includes taxes & fees
5 Oct - 6 Oct
Hilton Garden Inn Kent Island Marina
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 hotel reception area with a wooden reception desk, a minibar, and a wall with a textured pattern.

7. Hilton Garden Inn Bel Air

Hilton Garden Inn Bel Air
Bel Air
Canada
michelle
NZ$243
includes taxes & fees
12 Oct - 13 Oct
Hilton Garden Inn Bel Air
An outdoor patio with a stone fire pit, wicker furniture, and a view of the interior.
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.
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.

8. Home2 Suites by Hilton Baltimore / Aberdeen, MD

Home2 Suites by Hilton Baltimore / Aberdeen, MD
Aberdeen
United States
Adam
NZ$192
includes taxes & fees
4 Oct - 5 Oct
Home2 Suites by Hilton Baltimore / Aberdeen, MD
A modern lobby with a curved sofa, red armchairs, a fireplace, and a dining area with green chairs.
An outdoor patio with round tables and chairs, a barbecue grill, and umbrellas providing shade.
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.

9. Homewood Suites by Hilton Bel Air

Homewood Suites by Hilton Bel Air
Bel Air
United States
Jennifer
NZ$217
includes taxes & fees
6 Oct - 7 Oct
Homewood Suites by Hilton Bel Air
A spacious hotel lobby with a large seating area, a television, a fireplace, and a coffee station.
A hotel entrance with a covered parking area, a clear sign indicating 'Clearance 14' and 'Welcome' sign above the entrance.
A hotel room with a large bed, a desk with a television, a chair, and a nightstand with a lamp.
A gym with treadmills, elliptical machines, and a stationary bike.

10. Hampton Inn & Suites Baltimore/Aberdeen

Hampton Inn & Suites Baltimore/Aberdeen
Aberdeen
United States
Miguel
NZ$225
includes taxes & fees
4 Oct - 5 Oct
Hampton Inn & Suites Baltimore/Aberdeen
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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 Garfield Center for the Arts at the Prince Theater.
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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