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Check availability on Chestertown Gay-Friendly Hotels

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 Rp1.849.716
Rp2.114.778 total
includes taxes & fees
19 Apr - 20 Apr
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, (435 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 Rp1.217.576
Rp1.351.509 total
includes taxes & fees
21 Apr - 22 Apr
Red Roof Inn & Suites Chestertown

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (898 reviews)
"Best place to stay always "
United States
Robert
The price is Rp1.877.976
Rp2.084.553 total
includes taxes & fees
3 May - 4 May
Comfort Inn & Suites Chestertown

Vandiver Inn

Vandiver Inn
3.5 star property
Havre De Grace
9.4 out of 10, Exceptional, (542 reviews)
"As always we loved our stay! Definitely will be coming back "
United States
John
The price is Rp2.296.731
Rp2.572.339 total
includes taxes & fees
19 Apr - 20 Apr
Vandiver Inn

Flag House Inn

Flag House Inn
3.5 star property
Historic District
9.2 out of 10, Wonderful, (94 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 Rp3.110.092
Rp3.545.632 total
includes taxes & fees
20 Apr - 21 Apr
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, (331 reviews)
"The staff was lovely and so accommodating. Definitely the best part of our stay."
United States
Maritza
The price is Rp1.875.064
Rp2.100.072 total
includes taxes & fees
4 May - 5 May
Fairfield Inn & Suites by Marriott Aberdeen

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, (364 reviews)
"Staff was very friendly and it was a perfect location for us"
United States
Ryan
The price is Rp1.671.253
Rp1.871.803 total
includes taxes & fees
23 Apr - 24 Apr
Home2 Suites by Hilton Baltimore / Aberdeen, MD

Hampton Inn & Suites Baltimore/Aberdeen

Hampton Inn & Suites Baltimore/Aberdeen
2.5 star property
Aberdeen
9.0 out of 10, Wonderful, (636 reviews)
"Friendly and clean, great staff!"
United States
Sharon
The price is Rp1.615.076
Rp1.808.886 total
includes taxes & fees
3 May - 4 May
Hampton Inn & Suites Baltimore/Aberdeen

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, (987 reviews)
"Very nice hotel, good breakfast selection, clean rooms."
United States
Linda
The price is Rp2.140.875
Rp2.376.371 total
includes taxes & fees
27 Apr - 28 Apr
Holiday Inn Express Annapolis East-Kent Island by IHG

Courtyard Aberdeen at Ripken Stadium

Courtyard Aberdeen at Ripken Stadium
3.0 star property
Aberdeen
8.6 out of 10, Excellent, (227 reviews)
"Room were very clean, staff were excellent and friendly and helpful!"
United States
Matthew
The price is Rp1.441.237
Rp1.614.185 total
includes taxes & fees
4 May - 5 May
Courtyard Aberdeen at Ripken Stadium
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

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 Garfield Center for the Arts at the Prince Theater, Rolphs Wharf Marina and Northern Chesapeake Bay. While you're here, create some great memories of your trip with stops at Chesapeake Bay, Historical Society of Kent County Maryland 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.