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
7 Sep - 8 Sep
Tomorrow
8 Sep - 9 Sep
This weekend
11 Sep - 13 Sep
Next weekend
18 Sep - 20 Sep

Our top choices for Chestertown LGBT-friendly hotels

Free daily full breakfast
Lobby
Desk, laptop workspace, blackout curtains, iron/ironing board
Lobby

1. Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
Chestertown
United States
Amy
฿3,412
฿3,787 total
includes taxes & fees
4 Oct - 5 Oct
Comfort Inn & Suites Chestertown
Exterior
Desk, laptop workspace, blackout curtains, iron/ironing board
Lobby lounge
Desk, laptop workspace, blackout curtains, iron/ironing board

2. Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
Chestertown
United States
Linda
฿2,370
฿2,630 total
includes taxes & fees
13 Sept - 14 Sept
Red Roof Inn & Suites Chestertown
Private beach nearby, sun-loungers, beach volleyball
Private beach nearby, sun-loungers, beach volleyball
Reception
Property grounds

3. The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
Chestertown
United States
Lynda
฿3,555
฿4,065 total
includes taxes & fees
8 Sept - 9 Sept
The Lodge at Great Oak Landing
Exterior
Exterior
Standard Room, 1 King Bed, River View | Premium bedding, in-room safe, desk, iron/ironing board
Free daily buffet breakfast

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

Holiday Inn Express Annapolis East-Kent Island by IHG
Grasonville
United States
Emily
฿3,917
฿4,348 total
includes taxes & fees
5 Oct - 6 Oct
Holiday Inn Express Annapolis East-Kent Island by IHG
Terrace/patio
Indoor pool
Exterior
Free daily buffet breakfast

5. Home2 Suites by Hilton Baltimore / Aberdeen, MD

Home2 Suites by Hilton Baltimore / Aberdeen, MD
Aberdeen
United States
Eileen
฿3,212
฿3,598 total
includes taxes & fees
4 Oct - 5 Oct
Home2 Suites by Hilton Baltimore / Aberdeen, MD
Reception
Two queen studio suite | Bathroom | Combined shower/bathtub, free toiletries, hair dryer, towels
King suite whirlpool | Bathroom | Combined shower/bathtub, free toiletries, hair dryer, towels
Pool

6. Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South
Edgewood
United States
walter
฿2,786
฿3,120 total
includes taxes & fees
29 Sept - 30 Sept
Hampton Inn & Suites Edgewood/Aberdeen-South
Terrace/patio
Exterior
Restaurant
Exterior

7. Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
Grasonville
United States
roney
฿4,832
฿5,363 total
includes taxes & fees
4 Oct - 5 Oct
Hilton Garden Inn Kent Island Marina
Lobby lounge
View from property
Lobby
Desk, laptop workspace, blackout curtains, iron/ironing board

8. SpringHill Suites Baltimore White Marsh/Middle River

SpringHill Suites Baltimore White Marsh/Middle River
Middle River
United States
Jennifer
฿3,526
฿4,072 total
includes taxes & fees
13 Sept - 14 Sept
SpringHill Suites Baltimore White Marsh/Middle River
Terrace/patio
Dining
Exterior
Reception

9. Fairfield Inn & Suites by Marriott Aberdeen

Fairfield Inn & Suites by Marriott Aberdeen
Aberdeen
United States
Marie
฿3,643
฿4,080 total
includes taxes & fees
13 Sept - 14 Sept
Fairfield Inn & Suites by Marriott Aberdeen
Bar (on property)
Snack bar
Exterior
Reception

10. Hilton Garden Inn Bel Air

Hilton Garden Inn Bel Air
Bel Air
Canada
michelle
฿3,839
฿4,300 total
includes taxes & fees
27 Sept - 28 Sept
Hilton Garden Inn Bel Air
View all properties

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?
Comfort Inn & Suites Chestertown is a top LGBTQ-friendly hotel, and features free breakfast and free WiFi. Red Roof Inn & Suites Chestertown and The Lodge at Great Oak Landing 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 Chestertown Historic District, Northern Chesapeake Bay and Chesapeake Bay. While you're here, create some great memories of your trip with stops at Historical Society of Kent County Maryland, Rolphs Wharf Marina 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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