Aerial summer view of colonial Chestertown on the Chesapeake Bay in Maryland USA

Pet Friendly Hotels & Resorts in Chestertown from NZ$121

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Check availability on Chestertown Pet Friendly Hotels

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, (921 reviews)
"Great visit"
United States
Danielle
The price is NZ$205
includes taxes & fees
2 July - 3 July
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, (455 reviews)
"Nothing special but good for the price. "
United States
Andreas
The price is NZ$138
includes taxes & fees
17 June - 18 June
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 NZ$121
includes taxes & fees
11 June - 12 June
Driftwood Inn
Exterior detail

Vandiver Inn

Vandiver Inn
3.5 star property
Havre De Grace
9.4 out of 10, Exceptional, (550 reviews)
"The staff was wonderful! the place was nice and clean. everything was in walking distance. highly recommend staying here if visiting."
United States
Danielle
The price is NZ$279
includes taxes & fees
15 June - 16 June
Vandiver Inn
Meeting facility

Historic Inns of Annapolis

Historic Inns of Annapolis
3.5 star property
Historic District
9.0 out of 10, Wonderful, (1,871 reviews)
"Great hotel..will definitely be back"
United States
Randy
The price is NZ$265
includes taxes & fees
1 July - 2 July
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, (1,000 reviews)
"Good hotel for the price"
United States
Brenda
The price is NZ$209
includes taxes & fees
6 July - 7 July
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
7.8 out of 10, Good, (18 reviews)
"Nice place"
United States
christine
The price is NZ$151
includes taxes & fees
16 June - 17 June
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, (1,007 reviews)
"Great place to stay"
United States
Harry
The price is NZ$170
includes taxes & fees
16 June - 17 June
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, (380 reviews)
"Great stay at this"
United States
Wilson
The price is NZ$188
includes taxes & fees
18 June - 19 June
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, (661 reviews)
"Clean, comfortable, decent breakfast."
United States
Diane
The price is NZ$182
includes taxes & fees
21 June - 22 June
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 Baltimore N / White Marsh

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

6/10 Okay
"Elevators were down when we stayed. Although originally we were booked a room on the 5th floor, front desk was able to get us a room on the 4th floor…one less flight of stairs to go up and down. With two kids, one being 14 months old, it was a lot to go up and down the stairs. Other than that everything else was ok"
Ryan 1-night trip
Posted 17 hours 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 Rolphs Wharf Marina. While you're there, make sure you don't miss Northern Chesapeake Bay and Chesapeake Bay.