Pet friendly Hotels in Chestertown, Maryland

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Check prices for these dates

Tonight
Nov 14 - Nov 15
Tomorrow
Nov 15 - Nov 16
Next weekend
Nov 20 - Nov 22
In two weeks
Nov 27 - Nov 29

Our top choices for Chestertown pet-friendly hotels

A hotel lobby with a fireplace, seating area, and a television.

1. Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (1,000 reviews)
"The front desk staff were so nice, room very clean."
United States
John
The price is P6,139
P6,814 total
includes taxes & fees
Dec 6 - Dec 7
Comfort Inn & Suites Chestertown
A row of motel rooms with stone walls and red doors.

2. Driftwood Inn

Driftwood Inn
2.0 star property
Chestertown
5.4 out of 10, (183 reviews)
"It was a nice, clean place to stay the night."
United States
Kathy
The price is P4,044
P4,489 total
includes taxes & fees
Nov 20 - Nov 21
Driftwood Inn
A living room with a fireplace, a television, and a stone accent wall.

3. Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
2.0 star property
Chestertown
7.2 out of 10, Good, (514 reviews)
"Nice clean place and priced good. Plenty of mirrors, plenty of counter space, many tv channels even Christian based ones and comfortable bed. The room needs up dating since damage area on ceiling and corner location rug worn spot. I felt safe as a solo, could check in late and close to historic Chestertown. I would come again."
United States
Regina
The price is P4,585
P5,089 total
includes taxes & fees
Nov 22 - Nov 23
Red Roof Inn & Suites Chestertown
A rooftop terrace with wicker furniture, a fire pit, and a view of a marina.

4. Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.4 out of 10, Exceptional, (861 reviews)
"Great place to stay"
United States
Michael
The price is P8,540
P9,479 total
includes taxes & fees
Nov 17 - Nov 18
Hyatt Place Kent Narrows & Marina
Two Adirondack chairs facing a calm body of water with a clear sky above.

5. 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, (1,002 reviews)
"Helpful staff, nice location on the river"
United States
Suzanne
The price is P6,054
P6,720 total
includes taxes & fees
Dec 13 - Dec 14
Holiday Inn Express Annapolis East-Kent Island by IHG
A modern hotel lobby with a long dining table, several chairs, and a bar area.

6. Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South
2.5 star property
Edgewood
9.4 out of 10, Exceptional, (1,001 reviews)
"Very nice stay and staff"
United States
Deborah
The price is P5,431
P6,083 total
includes taxes & fees
Nov 22 - Nov 23
Hampton Inn & Suites Edgewood/Aberdeen-South
A modern building with a patio area featuring outdoor seating and a fire pit.

7. Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown
3.0 star property
Middletown
9.2 out of 10, Wonderful, (453 reviews)
"Beautiful and safe"
United States
Audra
The price is P7,897
P8,765 total
includes taxes & fees
Nov 29 - Nov 30
Fairfield Inn & Suites by Marriott Middletown
A patio with outdoor seating, overlooking a marina with boats.

8. Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
3.0 star property
Grasonville
8.8 out of 10, Excellent, (1,001 reviews)
"Everything was fantastic"
United States
Gamil
The price is P7,781
P8,637 total
includes taxes & fees
Nov 22 - Nov 23
Hilton Garden Inn Kent Island Marina
An outdoor patio with seating, a fire pit, and a barbecue area.

9. TownePlace Suites by Marriott Edgewood Aberdeen

TownePlace Suites by Marriott Edgewood Aberdeen
3.0 star property
Aberdeen
9.0 out of 10, Wonderful, (121 reviews)
"Great location, safe and great hotel"
United States
Armando
The price is P7,133
P7,989 total
includes taxes & fees
Nov 29 - Nov 30
TownePlace Suites by Marriott Edgewood Aberdeen
A hotel room with a large bed, a sofa, a TV, and a wall-mounted artwork.

10. SpringHill Suites by Marriott Edgewood/Aberdeen

SpringHill Suites by Marriott Edgewood/Aberdeen
3.0 star property
Bel Air
8.8 out of 10, Excellent, (408 reviews)
"good room, great staff"
United States
Nita
The price is P7,107
P7,960 total
includes taxes & fees
Nov 29 - Nov 30
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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Frequently Asked Questions

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 Historical Society of Kent County Maryland and Chestertown Historic District. While you're there, make sure you don't miss Rolphs Wharf Marina and Northern Chesapeake Bay.

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.