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Chestertown Hotel Guide - LGBT-Friendly Hotels in Chestertown, Maryland

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Check availability on Chestertown LGBT-Friendly Hotels

Top Chestertown LGBT-Friendly Hotels

Our top choices for Chestertown LGBT-friendly hotels

The Lodge at Great Oak Landing
Private beach nearby, sun-loungers, beach volleyball

The Lodge at Great Oak Landing

3.5 star property
8.0 out of 10, Very good, (68)
"Everything was perfect. The staff is super friendly, the room was clean and fresh. The beds were super comfy, the food is amazing and the chef was super nice!! Great friendly atmosphere. I’m definitely going back!!"
The price is €125
includes taxes & fees
24 Sept - 25 Sept
The Lodge at Great Oak Landing
Vandiver Inn
The Stokes (Standard / 2nd Floor Vandiver Mansion) | Terrace/patio

Vandiver Inn

3.5 star property
9.4 out of 10, Exceptional, (518)
"Been to the Vandiver many times and are always pleasantly pleased."
Vandiver Inn
Holiday Inn Express & Suites Middletown by IHG
Exterior

Holiday Inn Express & Suites Middletown by IHG

2.5 star property
9.2 out of 10, Wonderful, (619)
"Check in staff was awesome!"
The price is €101
includes taxes & fees
28 Sept - 29 Sept
Holiday Inn Express & Suites Middletown by IHG
Holiday Inn Express Annapolis East-Kent Island by IHG
Exterior

Holiday Inn Express Annapolis East-Kent Island by IHG

2.5 star property
9.2 out of 10, Wonderful, (902)
"The BEAUTIFUL backyard on the water, the walking trail, and the walkability to several restaurants were so nice!"
The price is €127
includes taxes & fees
19 Oct - 20 Oct
Holiday Inn Express Annapolis East-Kent Island by IHG
Comfort Inn & Suites Chestertown
Lobby

Comfort Inn & Suites Chestertown

2.5 star property
8.6 out of 10, Excellent, (819)
"Friendly staff, clean room, convenient location. "
The price is €110
includes taxes & fees
28 Sept - 29 Sept
Comfort Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
Suite, Multiple Beds, Non Smoking

Red Roof Inn & Suites Chestertown

2.0 star property
7.2 out of 10, Good, (395)
"We had a great stay with our two Pups.. The room was very nice and comfortable and very clean."
The price is €72
includes taxes & fees
29 Sept - 30 Sept
Red Roof Inn & Suites Chestertown
Hampton Inn & Suites Edgewood/Aberdeen-South
Restaurant

Hampton Inn & Suites Edgewood/Aberdeen-South

2.5 star property
9.4 out of 10, Exceptional, (1005)
"Very good breakfast options Convenient parking Clean room Friendly staff"
The price is €84
includes taxes & fees
28 Sept - 29 Sept
Hampton Inn & Suites Edgewood/Aberdeen-South
Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
Exterior

Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG

2.5 star property
9.0 out of 10, Wonderful, (520)
"Clean room, staff helpful, parking aplenty. "
The price is €83
includes taxes & fees
29 Sept - 30 Sept
Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
Hampton Inn Middletown
Reception

Hampton Inn Middletown

2.5 star property
8.8 out of 10, Excellent, (833)
"Decent for a Hampton Inn"
The price is €103
includes taxes & fees
30 Sept - 1 Oct
Hampton Inn Middletown
Hilton Garden Inn Baltimore/White Marsh
Exterior

Hilton Garden Inn Baltimore/White Marsh

3.0 star property
7.8 out of 10, Good, (1014)
"Nice clean hotel with very friendly staff"
The price is €100
includes taxes & fees
24 Sept - 25 Sept
Hilton Garden Inn Baltimore/White Marsh
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

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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 Historical Society of Kent County Maryland, Rolphs Wharf Marina and Garfield Center for the Arts at the Prince Theater. While you're here, create some great memories of your trip with stops at Chestertown Historic District, Sumner Hall and Urieville Park.
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.