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Check availability on Chestertown Gay-Friendly Hotels

Top Chestertown Gay-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
7.8 out of 10, Good, (70)
"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 ฿4,325
฿4,945 total
includes taxes & fees
14 Oct - 15 Oct
The Lodge at Great Oak Landing
Comfort Inn & Suites Chestertown
Lobby

Comfort Inn & Suites Chestertown

2.5 star property
8.6 out of 10, Excellent, (826)
"Friendly staff, clean room, convenient location. "
The price is ฿3,335
฿3,701 total
includes taxes & fees
19 Oct - 20 Oct
Comfort Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
Suite, Multiple Beds, Non Smoking | 1 bedroom, desk, laptop workspace, blackout curtains

Red Roof Inn & Suites Chestertown

2.0 star property
7.2 out of 10, Good, (402)
"We had a great stay with our two Pups.. The room was very nice and comfortable and very clean."
The price is ฿2,648
฿2,939 total
includes taxes & fees
19 Oct - 20 Oct
Red Roof Inn & Suites Chestertown
Hampton Inn & Suites Baltimore/Aberdeen
Restaurant

Hampton Inn & Suites Baltimore/Aberdeen

2.5 star property
9.0 out of 10, Wonderful, (583)
"This Hotel was excellent in all ways. "
The price is ฿3,190
฿3,573 total
includes taxes & fees
21 Oct - 22 Oct
Hampton Inn & Suites Baltimore/Aberdeen
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, (626)
"Check in staff was awesome!"
The price is ฿3,374
฿3,745 total
includes taxes & fees
19 Oct - 20 Oct
Holiday Inn Express & Suites Middletown by IHG
Hilton Garden Inn Baltimore/White Marsh
Exterior

Hilton Garden Inn Baltimore/White Marsh

3.0 star property
7.8 out of 10, Good, (1012)
"Great stay"
The price is ฿3,121
฿3,605 total
includes taxes & fees
16 Oct - 17 Oct
Hilton Garden Inn Baltimore/White Marsh
Hampton Inn & Suites Edgewood/Aberdeen-South
Restaurant

Hampton Inn & Suites Edgewood/Aberdeen-South

2.5 star property
9.4 out of 10, Exceptional, (1005)
"Love love love this hotel they provided me with excellent care. Also helped me out with late checkout as needed. Great stay booking again very soon "
The price is ฿2,734
฿3,062 total
includes taxes & fees
11 Nov - 12 Nov
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, (527)
"Super clean, a great place to stay"
The price is ฿2,720
฿3,046 total
includes taxes & fees
20 Oct - 21 Oct
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, (839)
"Enjoyed the amenities and great location for shops nearby "
The price is ฿3,512
฿3,898 total
includes taxes & fees
2 Nov - 3 Nov
Hampton Inn Middletown
Historic Inns of Annapolis
Terrace/patio

Historic Inns of Annapolis

3.5 star property
9.0 out of 10, Wonderful, (1846)
"Perfect location…terrific staff…spacious room with a king sized bed! "
Historic Inns of Annapolis
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.