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

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Check availability on Chestertown Gay-Friendly Hotels

Our top choices for Chestertown LGBT-friendly hotels

Free daily full breakfast

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (930 reviews)
"Great visit"
United States
Danielle
The price is Rp1.931.101
Rp2.143.522 total
includes taxes & fees
6 Aug - 7 Aug
Comfort Inn & Suites Chestertown
Exterior

Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG
2.5 star property
Grasonville
9.2 out of 10, Wonderful, (1,006 reviews)
"Beautiful view!!! Clean hotel and very nice helpful staff. Would stay again."
United States
Michele
The price is Rp2.286.517
Rp2.538.034 total
includes taxes & fees
23 Jul - 24 Jul
Holiday Inn Express Annapolis East-Kent Island by IHG
Exterior

Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG

Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
2.5 star property
Edgewood
9.0 out of 10, Wonderful, (616 reviews)
"Hotel was clean and staff were kind and friendly."
United States
Efua
The price is Rp1.740.288
Rp1.949.124 total
includes taxes & fees
10 Aug - 11 Aug
Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
Lobby lounge

Flag House Inn

Flag House Inn
3.5 star property
Historic District
9.2 out of 10, Wonderful, (94 reviews)
"Great location. Beautiful room and exemplary service. "
United States
Nathan
The price is Rp4.092.961
Rp4.665.986 total
includes taxes & fees
12 Jul - 13 Jul
Flag House Inn
Private beach nearby, sun-loungers, beach volleyball

The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
3.0 star property
Chestertown
7.8 out of 10, Good, (90 reviews)
"Peaceful and beautiful location. Such a relaxing spot. Very clean throughout the whole property. Staff very pleasant and attentive. Would stay here again "
United States
Nicola
The price is Rp2.383.252
Rp2.724.771 total
includes taxes & fees
13 Jul - 14 Jul
The Lodge at Great Oak Landing
Lobby lounge

Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
2.0 star property
Chestertown
7.2 out of 10, Good, (460 reviews)
"Perfect for an overnight trip, staff was very helpful."
United States
Anasmel
The price is Rp1.296.846
Rp1.439.499 total
includes taxes & fees
21 Jul - 22 Jul
Red Roof Inn & Suites Chestertown
Exterior

Holiday Inn Express & Suites Middletown by IHG

Holiday Inn Express & Suites Middletown by IHG
2.5 star property
Middletown
9.2 out of 10, Wonderful, (698 reviews)
"Very clean enjoyed my stay"
United States
Yahira
The price is Rp1.849.317
Rp2.052.695 total
includes taxes & fees
19 Jul - 20 Jul
Holiday Inn Express & Suites Middletown by IHG
Desk, laptop workspace, iron/ironing board, free WiFi

SpringHill Suites by Marriott Edgewood/Aberdeen

SpringHill Suites by Marriott Edgewood/Aberdeen
3.0 star property
Bel Air
8.8 out of 10, Excellent, (388 reviews)
"No complaints"
United States
Sandesh
The price is Rp2.104.661
Rp2.357.219 total
includes taxes & fees
2 Aug - 3 Aug
SpringHill Suites by Marriott Edgewood/Aberdeen
Meeting facility

Historic Inns of Annapolis

Historic Inns of Annapolis
3.5 star property
Historic District
9.0 out of 10, Wonderful, (1,892 reviews)
"Easy check in, easy valet, great location. Overall, very nice stay!"
United States
Caitlin
The price is Rp1.624.204
Rp2.467.671 total
includes taxes & fees
19 Jul - 20 Jul
Historic Inns of Annapolis
Reception

Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South
2.5 star property
Edgewood
9.4 out of 10, Exceptional, (1,012 reviews)
"Nice hotel with friendly staff."
United States
Alia
The price is Rp1.684.998
Rp1.887.196 total
includes taxes & fees
10 Aug - 11 Aug
Hampton Inn & Suites Edgewood/Aberdeen-South
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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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.