Photo by Assya A

Gay friendly Hotels in Chestertown, Maryland

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
Oct 2 - Oct 3
Tomorrow
Oct 3 - Oct 4
This weekend
Oct 3 - Oct 5
Next weekend
Oct 10 - Oct 12

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 P7,385
P8,198 total
includes taxes & fees
Oct 19 - Oct 20
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, (623)
"Check in staff was awesome!"
The price is P6,746
P7,488 total
includes taxes & fees
Oct 12 - Oct 13
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 P7,693
P8,540 total
includes taxes & fees
Oct 5 - Oct 6
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, (1000)
"Very good breakfast options Convenient parking Clean room Friendly staff"
The price is P5,141
P5,757 total
includes taxes & fees
Oct 12 - Oct 13
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 P6,663
P7,396 total
includes taxes & fees
Nov 2 - Nov 3
Comfort Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
1 bedroom, desk, laptop workspace, blackout drapes

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 P4,710
P5,228 total
includes taxes & fees
Oct 8 - Oct 9
Red Roof Inn & Suites Chestertown
Vandiver Inn
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 P5,350
P5,992 total
includes taxes & fees
Oct 28 - Oct 29
Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
SpringHill Suites Baltimore White Marsh/Middle River
Desk, laptop workspace, blackout drapes, 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 P7,126
P8,231 total
includes taxes & fees
Oct 5 - Oct 6
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 P5,122
P5,736 total
includes taxes & fees
Oct 5 - Oct 6
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

Looking for a gay-friendly accommodation in Chestertown?
Whether you are traveling with your partner or flying solo, you'll find LGBTQ-friendly hotels in Chestertown on Expedia. Discover the people, places, and traditions found only in Chestertown.
What is the favorite LGBTQ-friendly accommodation 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 two other good choices for your stay.
How many gay-friendly hotels will I find in Chestertown?
There are currently 3 LGBTQ-friendly lodging options in Chestertown.
What should I do while I'm visiting Chestertown?
During your vacation, get out and enjoy everything Chestertown is known for. You and your traveling 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, also known as gay-friendly hotels, welcome all travelers who identify as LGBTQIA+. Expedia has compiled a selection of LGBTQ-friendly hotels worldwide. In Chestertown, these hotels will provide lesbian, gay, bisexual, and transgender adventurers with the information needed to design the trip of a lifetime.
What can I expect from an LGBTQ-friendly accommodation in Chestertown?
Stay at an LGBTQ-friendly hotel in Chestertown and the staff will help you explore the local gay scene and the LGBTQ+ culture. Some of Expedia's LGBTQ-friendly hotels go the extra mile and offer wedding ceremonies and honeymoon packages for same-sex couples.