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
10 Aug - 11 Aug
Tomorrow
11 Aug - 12 Aug
This weekend
14 Aug - 16 Aug
Next weekend
21 Aug - 23 Aug

Our top choices for Chestertown LGBT-friendly hotels

Free daily full breakfast
Lobby
Lobby
Point of interest

1. Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
Chestertown
United States
Deanna
฿3,544
฿3,934 total
includes taxes & fees
31 Aug - 1 Sept
Comfort Inn & Suites Chestertown
Lobby lounge
Suite, Multiple Beds, Non Smoking | Desk, laptop workspace, blackout curtains, iron/ironing board
Lobby lounge
Exterior

2. Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
Chestertown
United States
Anasmel
฿2,083
฿2,312 total
includes taxes & fees
17 Aug - 18 Aug
Red Roof Inn & Suites Chestertown
Private beach nearby, sun-loungers, beach volleyball
Property grounds
Reception
Private beach nearby, sun-loungers, beach volleyball

3. The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
Chestertown
United States
Nicola
฿3,571
฿4,082 total
includes taxes & fees
12 Aug - 13 Aug
The Lodge at Great Oak Landing
Lobby lounge
Exterior
View from property
Desk, laptop workspace, blackout curtains, iron/ironing board

4. SpringHill Suites Baltimore White Marsh/Middle River

SpringHill Suites Baltimore White Marsh/Middle River
Middle River
United States
KaTerra
฿3,541
฿4,090 total
includes taxes & fees
20 Aug - 21 Aug
SpringHill Suites Baltimore White Marsh/Middle River
Exterior detail
Room, Private Bathroom (O'Neill) | Living area | Flat-screen TV
Dining
Exterior

5. Vandiver Inn

Vandiver Inn
Havre De Grace
United States
Shannon
฿5,308
฿5,945 total
includes taxes & fees
11 Aug - 12 Aug
Vandiver Inn
Exterior
Exterior
Standard Room, 1 King Bed, River View | Premium bedding, in-room safe, desk, iron/ironing board
Free daily buffet breakfast

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

Holiday Inn Express Annapolis East-Kent Island by IHG
Grasonville
United States
Jackie
฿3,934
฿4,367 total
includes taxes & fees
7 Sept - 8 Sept
Holiday Inn Express Annapolis East-Kent Island by IHG
Terrace/patio
Exterior
Indoor pool
Free daily buffet breakfast

7. Home2 Suites by Hilton Baltimore / Aberdeen, MD

Home2 Suites by Hilton Baltimore / Aberdeen, MD
Aberdeen
United States
Mark
฿3,226
฿3,613 total
includes taxes & fees
16 Aug - 17 Aug
Home2 Suites by Hilton Baltimore / Aberdeen, MD
Bar (on property)
Snack bar
Exterior
Terrace/patio

8. Hilton Garden Inn Bel Air

Hilton Garden Inn Bel Air
Bel Air
United States
Calandra
฿3,768
฿4,220 total
includes taxes & fees
30 Aug - 31 Aug
Hilton Garden Inn Bel Air
Terrace/patio
Dining
Lobby lounge
Reception

9. Fairfield Inn & Suites by Marriott Aberdeen

Fairfield Inn & Suites by Marriott Aberdeen
Aberdeen
United States
Marie
฿3,620
฿4,054 total
includes taxes & fees
11 Aug - 12 Aug
Fairfield Inn & Suites by Marriott Aberdeen
Reception
Exterior
Reception
Reception

10. Hilton Garden Inn Aberdeen

Hilton Garden Inn Aberdeen
Aberdeen
United States
Jayden
฿3,633
฿4,069 total
includes taxes & fees
16 Aug - 17 Aug
Hilton Garden Inn 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?
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, Rolphs Wharf Marina and Northern Chesapeake Bay. While you're here, create some great memories of your trip with stops at Chesapeake Bay, Historical Society of Kent County Maryland 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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