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Check availability on Chestertown Gay-Friendly Hotels

This weekend
29 May - 31 May
Next weekend
5 Jun - 7 Jun

Our top choices for Chestertown LGBT-friendly hotels

Private beach nearby, sun-loungers, beach volleyball

The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
3.5 star property
Chestertown
8.0 out of 10, Very good, (82 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 Rp2.343.959
Rp2.679.849 total
includes taxes & fees
1 Jun - 2 Jun
The Lodge at Great Oak Landing
Free daily full breakfast

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (913 reviews)
"Great visit"
United States
Danielle
The price is Rp1.962.335
Rp2.178.192 total
includes taxes & fees
15 Jun - 16 Jun
Comfort Inn & Suites Chestertown
Lobby lounge

Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
2.0 star property
Chestertown
7.2 out of 10, Good, (442 reviews)
"Nothing special but good for the price. "
United States
Andreas
The price is Rp1.275.465
Rp1.415.766 total
includes taxes & fees
1 Jun - 2 Jun
Red Roof Inn & Suites Chestertown
Exterior detail

Vandiver Inn

Vandiver Inn
3.5 star property
Havre De Grace
9.4 out of 10, Exceptional, (545 reviews)
"A beautiful and romantic Victorian B&B with friendly staff and delicious breakfast. We absolutely loved our stay and would go back again if we were ever in the area."
United States
Shannon
The price is Rp2.560.018
Rp2.867.220 total
includes taxes & fees
31 May - 1 Jun
Vandiver Inn
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, (1,000 reviews)
"We were very pleased with our overnight here - it was economical and more than sufficient. It was clean, comfortable and it was nice to have breakfast included (try the cinnamon buns!) "
United States
Susan
The price is Rp2.374.078
Rp2.635.227 total
includes taxes & fees
7 Jun - 8 Jun
Holiday Inn Express Annapolis East-Kent Island 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 Rp3.860.003
Rp4.400.371 total
includes taxes & fees
26 May - 27 May
Flag House Inn
Terrace/patio

Home2 Suites by Hilton Baltimore / Aberdeen, MD

Home2 Suites by Hilton Baltimore / Aberdeen, MD
3.0 star property
Aberdeen
8.8 out of 10, Excellent, (378 reviews)
"Great stay at this"
United States
Wilson
The price is Rp1.728.825
Rp1.936.285 total
includes taxes & fees
7 Jun - 8 Jun
Home2 Suites by Hilton Baltimore / Aberdeen, MD
Terrace/patio

Fairfield Inn & Suites by Marriott Aberdeen

Fairfield Inn & Suites by Marriott Aberdeen
3.0 star property
Aberdeen
9.0 out of 10, Wonderful, (340 reviews)
"Very sweet young lady who checked us in. Nice property, great location!"
United States
Andrea
The price is Rp1.939.657
Rp2.172.415 total
includes taxes & fees
9 Jun - 10 Jun
Fairfield Inn & Suites by Marriott Aberdeen
Reception

Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South
2.5 star property
Edgewood
9.4 out of 10, Exceptional, (1,003 reviews)
"Best place to stay"
United States
Victor
The price is Rp1.602.503
Rp1.794.803 total
includes taxes & fees
2 Jun - 3 Jun
Hampton Inn & Suites Edgewood/Aberdeen-South
Lobby

Hampton Inn & Suites Baltimore/Aberdeen

Hampton Inn & Suites Baltimore/Aberdeen
2.5 star property
Aberdeen
9.0 out of 10, Wonderful, (656 reviews)
"Clean, comfortable, decent breakfast."
United States
Diane
The price is Rp1.670.713
Rp1.871.199 total
includes taxes & fees
7 Jun - 8 Jun
Hampton Inn & Suites Baltimore/Aberdeen
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 Rolphs Wharf Marina, Northern Chesapeake Bay and Chesapeake Bay. While you're here, create some great memories of your trip with stops at Historical Society of Kent County Maryland, Garfield Center for the Arts at the Prince Theater and Chestertown Historic District.
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.