Photo by Assya A

Search Gay-Friendly Hotels in Chestertown

Start date: Check-in selected.
To Date
End date: Check-out
    calendar shield illustration

    Change your mind

    Book hotels with free cancellation
    deals illustration

    Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration

    Be picky

    Search almost a million properties worldwide

Check availability on Chestertown Gay-Friendly Hotels

Tonight
3 Oct - 4 Oct
Tomorrow
4 Oct - 5 Oct
This weekend
3 Oct - 5 Oct
Next weekend
10 Oct - 12 Oct

Top Chestertown Gay-Friendly Hotels

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, (903)
"The BEAUTIFUL backyard on the water, the walking trail, and the walkability to several restaurants were so nice!"
The price is 3.352.292 ₫
3.721.044 ₫ total
includes taxes & fees
19 Oct - 20 Oct
Holiday Inn Express Annapolis East-Kent Island by IHG
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, (624)
"Check in staff was awesome!"
The price is 3.061.936 ₫
3.398.749 ₫ total
includes taxes & fees
19 Oct - 20 Oct
Holiday Inn Express & Suites Middletown by IHG
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 3.492.191 ₫
3.992.622 ₫ total
includes taxes & fees
7 Oct - 8 Oct
The Lodge at Great Oak Landing
Hampton Inn & Suites Edgewood/Aberdeen-South
Restaurant

Hampton Inn & Suites Edgewood/Aberdeen-South

2.5 star property
9.4 out of 10, Exceptional, (1001)
"Very good breakfast options Convenient parking Clean room Friendly staff"
The price is 2.333.406 ₫
2.613.414 ₫ total
includes taxes & fees
9 Oct - 10 Oct
Hampton Inn & Suites Edgewood/Aberdeen-South
Comfort Inn & Suites Chestertown
Lobby

Comfort Inn & Suites Chestertown

2.5 star property
8.6 out of 10, Excellent, (825)
"Friendly staff, clean room, convenient location. "
The price is 3.019.966 ₫
3.352.163 ₫ total
includes taxes & fees
3 Nov - 4 Nov
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, (399)
"We had a great stay with our two Pups.. The room was very nice and comfortable and very clean."
The price is 2.138.076 ₫
2.373.264 ₫ total
includes taxes & fees
27 Oct - 28 Oct
Red Roof Inn & Suites Chestertown
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 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, (525)
"Super clean, a great place to stay"
The price is 2.428.432 ₫
2.719.844 ₫ total
includes taxes & fees
12 Oct - 13 Oct
Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
SpringHill Suites Baltimore White Marsh/Middle River
Desk, laptop workspace, blackout curtains, iron/ironing board

SpringHill Suites Baltimore White Marsh/Middle River

2.5 star property
9.0 out of 10, Wonderful, (743)
"Great place to stay, better than any of the other hotels in the middle river area."
The price is 3.234.830 ₫
3.736.090 ₫ total
includes taxes & fees
12 Oct - 13 Oct
SpringHill Suites Baltimore White Marsh/Middle River
Holiday Inn Belcamp - Aberdeen Area by IHG
Exterior

Holiday Inn Belcamp - Aberdeen Area by IHG

3.0 star property
8.4 out of 10, Very good, (724)
"It was a good location. Workers are super friendly and attentive. "
The price is 2.324.520 ₫
2.603.462 ₫ total
includes taxes & fees
5 Oct - 6 Oct
Holiday Inn Belcamp - Aberdeen Area by IHG
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.
View all properties

Top Chestertown Hotel Reviews

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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.
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.