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Check availability on Chestertown Pet-friendly Hotels

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

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, (913 reviews)
"Great visit"
United States
Danielle
The price is ₩161,218
₩178,952 total
includes taxes & fees
Jun 21 - Jun 22
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, (444 reviews)
"Nothing special but good for the price. "
United States
Andreas
The price is ₩108,825
₩120,795 total
includes taxes & fees
Jun 2 - Jun 3
Red Roof Inn & Suites Chestertown
Front of property - evening/night

Driftwood Inn

Driftwood Inn
2.0 star property
Chestertown
5.2 out of 10, (176 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 ₩95,990
₩106,556 total
includes taxes & fees
May 28 - May 29
Driftwood 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 location"
United States
Stephanie
The price is ₩175,605
₩252,088 total
includes taxes & fees
Jun 8 - Jun 9
Historic Inns of Annapolis
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 ₩218,426
₩244,638 total
includes taxes & fees
May 31 - Jun 1
Vandiver Inn
Indoor pool

Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
2.5 star property
Grasonville
8.0 out of 10, Very Good, (1,003 reviews)
"It is a nice Hotel."
United States
Dale
The price is ₩173,961
₩193,096 total
includes taxes & fees
Jun 2 - Jun 3
Best Western Kent Narrows Inn
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, (1,001 reviews)
"Great place to stay"
United States
Harry
The price is ₩133,630
₩149,666 total
includes taxes & fees
Jun 9 - Jun 10
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 ₩148,077
₩165,847 total
includes taxes & fees
Jun 7 - Jun 8
Home2 Suites by Hilton Baltimore / Aberdeen, MD
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 ₩142,549
₩159,655 total
includes taxes & fees
Jun 21 - Jun 22
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

La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

8/10 Good
"Decent hotel for the night"
Michelle 1-night trip
Posted 11 hours ago
La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

Frequently asked questions

What's the best pet-friendly accommodation in Chestertown?
Comfort Inn & Suites Chestertown is a top hotel for people traveling with their pets, and offers a seasonal outdoor pool and a fitness center for its human guests. Other good choices for you and 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 temp of 74°F, while the coldest months are January and February with an average of 39°F. Average annual precipitation for Chestertown is 48 inches.
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 Rolphs Wharf Marina and Northern Chesapeake Bay. While you're there, make sure you don't miss Chesapeake Bay and Historical Society of Kent County Maryland.