Chestertown Hotel Guide - Pet Friendly Hotels in Chestertown, Maryland

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Check availability on Chestertown Pet Friendly Hotels

Next weekend
5 Jun - 7 Jun
In two weeks
12 Jun - 14 Jun

Our top choices for Chestertown pet-friendly hotels

Free daily full breakfast

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (915 reviews)
"Great visit"
United States
Danielle
The price is €104
includes taxes & fees
23 Jun - 24 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, (449 reviews)
"Nothing special but good for the price. "
United States
Andreas
The price is €69
includes taxes & fees
8 Jun - 9 Jun
Red Roof Inn & Suites Chestertown
Front of property – evening/night

Driftwood Inn

Driftwood Inn
2.0 star property
Chestertown
5.2 out of 10, (177 reviews)
"Terrible !!! Dirty not clean the owner was rude and didn’t care about the conditions of the room. I asked for partial refund and was denied. Rat poop in the heaters. Dog hair in tubs dead bugs. Body fluids everywhere! Also drug dealers outside with guns. The owner still didn’t care what they were doing. Don’t go to this place it should be shut down !"
United States
Gabriel
The price is €60
includes taxes & fees
1 Jun - 2 Jun
Driftwood Inn
Exterior detail

Vandiver Inn

Vandiver Inn
3.5 star property
Havre De Grace
9.4 out of 10, Exceptional, (547 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 €139
includes taxes & fees
1 Jun - 2 Jun
Vandiver Inn
Meeting facility

Historic Inns of Annapolis

Historic Inns of Annapolis
3.5 star property
Historic District
9.0 out of 10, Wonderful, (1,853 reviews)
"Great hotel..will definitely be back"
United States
Randy
The price is €143
includes taxes & fees
8 Jun - 9 Jun
Historic Inns of Annapolis
Indoor pool

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very good, (1,005 reviews)
"Good hotel for the price"
United States
Brenda
The price is €110
includes taxes & fees
16 Jun - 17 Jun
Best Western Kent Narrows Inn
TV

Charming 2-bedroom house in Aberdeen with WiFi and AC

Charming 2-bedroom house in Aberdeen with WiFi and AC
Aberdeen
8.2 out of 10, Very good, (17 reviews)
"Nice place"
United States
christine
The price is €75
includes taxes & fees
3 Jun - 4 Jun
Charming 2-bedroom house in Aberdeen with WiFi and AC
Exterior

La Quinta Inn & Suites by Wyndham Aberdeen-APG

La Quinta Inn & Suites by Wyndham Aberdeen-APG
3.0 star property
Aberdeen
9.0 out of 10, Wonderful, (1,002 reviews)
"Great place to stay"
United States
Harry
The price is €85
includes taxes & fees
7 Jun - 8 Jun
La Quinta Inn & Suites by Wyndham Aberdeen-APG
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 €94
includes taxes & fees
7 Jun - 8 Jun
Home2 Suites by Hilton Baltimore / Aberdeen, MD
Desk, laptop workspace, iron/ironing board, free WiFi

SpringHill Suites by Marriott Edgewood/Aberdeen

SpringHill Suites by Marriott Edgewood/Aberdeen
3.0 star property
Bel Air
8.8 out of 10, Excellent, (384 reviews)
"Love this awesome place best around "
United States
Christopher
The price is €111
includes taxes & fees
7 Jun - 8 Jun
SpringHill Suites by Marriott Edgewood/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

La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

2/10 Terrible
"Long-term residents on 1st floor, big bag of trash outside numerous doors, elevator broken, stairway smelled like urine, and outside was dirty and appeared unsafe . I checked in and checked out within 5 mins."
Christopher 1-night trip
Posted 1 day ago
La Quinta Inn & Suites by Wyndham Baltimore N / White Marsh

Frequently asked questions

What's the best dog-friendly accommodation option in Chestertown?
Comfort Inn & Suites Chestertown is a top hotel for people travelling with their pets, and offers a seasonal outdoor pool and a fitness centre for its human guests. Two other good options to stay with your pet include Red Roof Inn & Suites Chestertown and Driftwood Inn.
What's the best time of year to travel to Chestertown with my pet?
When you travel with your pet, keeping tabs on the weather can make the trip safe and fun for everyone. The hottest months are usually July and August, with an average temperature of 23°C, while the coldest months are January and February, with an average of 4°C. Average annual precipitation for Chestertown is 1232 mm.
What is there to see and do with your pet in Chestertown?
Known for its sports, Chestertown has lots to offer visitors, including its university life and festivals. See the local sights and visit Chestertown Historic District and Northern Chesapeake Bay. While you're there, make sure you don't miss Chesapeake Bay and Historical Society of Kent County Maryland.