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Our top choices for Chestertown LGBT-friendly hotels

The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
3.5 star property
Chestertown
7.8 out of 10, Good, (77 reviews)
"Very nice rooms, "
United States
Stephania
The price is ₩162,086
₩185,315 total
includes taxes & fees
Mar 29 - Mar 30
The Lodge at Great Oak Landing

Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
2.0 star property
Chestertown
7.2 out of 10, Good, (432 reviews)
"Arrived earlier than expected and the staff was very accommodating and friendly which made for an excellent stay from start to finish. "
United States
Linette
The price is ₩101,291
₩112,433 total
includes taxes & fees
Apr 22 - Apr 23
Red Roof Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (891 reviews)
"Staying is peaceful and the rooms clean."
United States
Robert
The price is ₩171,164
₩189,992 total
includes taxes & fees
Apr 13 - Apr 14
Comfort Inn & Suites Chestertown

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, (356 reviews)
"Staff was very friendly and it was a perfect location for us"
United States
Ryan
The price is ₩146,588
₩164,180 total
includes taxes & fees
Apr 8 - Apr 9
Home2 Suites by Hilton Baltimore / Aberdeen, MD

Vandiver Inn

Vandiver Inn
3.5 star property
Havre De Grace
9.4 out of 10, Exceptional, (538 reviews)
"As always we loved our stay! Definitely will be coming back "
United States
John
The price is ₩201,449
₩225,623 total
includes taxes & fees
Mar 29 - Mar 30
Vandiver Inn

Flag House Inn

Flag House Inn
3.5 star property
Historic District
9.2 out of 10, Wonderful, (90 reviews)
"The B&B website and other on-line links claims "...excellent breakfast" and "the best breakfast in Annapolis". What was served were mini grocery store bought pastry, no fresh coffee, no juice, no plates, no one around. In addition, they state that for a large fee you can have valet parking on-site. There was no valet. I requested a refund for the valet parking and used that money to have a decent breakfast elsewhere. "
United States
Linda
The price is ₩272,530
₩310,695 total
includes taxes & fees
Mar 31 - Apr 1
Flag House Inn

Fairfield Inn & Suites by Marriott Aberdeen

Fairfield Inn & Suites by Marriott Aberdeen
3.0 star property
Aberdeen
9.0 out of 10, Wonderful, (322 reviews)
"room was clean breakfast good staff very friendly"
United States
Robin
The price is ₩164,464
₩184,198 total
includes taxes & fees
Mar 29 - Mar 30
Fairfield Inn & Suites by Marriott Aberdeen

Hilton Garden Inn Aberdeen

Hilton Garden Inn Aberdeen
3.0 star property
Aberdeen
8.6 out of 10, Excellent, (643 reviews)
"Quiet, clean, and friendly staff."
United States
William
The price is ₩148,270
₩166,062 total
includes taxes & fees
Apr 7 - Apr 8
Hilton Garden Inn Aberdeen

Hampton Inn & Suites Baltimore/Aberdeen

Hampton Inn & Suites Baltimore/Aberdeen
2.5 star property
Aberdeen
9.0 out of 10, Wonderful, (629 reviews)
"Friendly and clean, great staff!"
United States
Sharon
The price is ₩153,832
₩172,292 total
includes taxes & fees
Apr 12 - Apr 13
Hampton Inn & Suites Baltimore/Aberdeen

Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG

Holiday Inn Express Edgewood-Aberdeen-Bel Air by IHG
2.5 star property
Edgewood
9.0 out of 10, Wonderful, (580 reviews)
"No bar soap "
United States
Fataira
The price is ₩130,570
₩146,238 total
includes taxes & fees
Mar 30 - Mar 31
Holiday Inn Express Edgewood-Aberdeen-Bel Air 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.

Top Chestertown Hotel Reviews

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 Northern Chesapeake Bay. While you're here, create some great memories of your trip with stops at Chesapeake Bay, Garfield Center for the Arts at the Prince Theater, and Chestertown Historic District.
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.