An aerial view of a town with a river, buildings, and surrounding greenery.

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Check availability on Chestertown Pet-friendly Hotels

This weekend
30 Oct - 1 Nov
Next weekend
6 Nov - 8 Nov

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, (995 reviews)
"Good hotel"
United States
Michael
The price is AED 362
AED 401 total
includes taxes & fees
18 Nov - 19 Nov
Comfort Inn & Suites Chestertown
A living room with a fireplace, a television, and a stone accent wall.

2. Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
2.0 star property
Chestertown
7.2 out of 10, Good, (511 reviews)
"Friendly staff, plenty of parking spaces,family friendly. The building is old but would do some renovation. Furniture needs replacement."
United States
Mary
The price is AED 264
AED 294 total
includes taxes & fees
2 Nov - 3 Nov
Red Roof Inn & Suites Chestertown
A row of motel rooms with stone walls and red doors.

3. 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 AED 233
AED 259 total
includes taxes & fees
28 Oct - 29 Oct
Driftwood Inn
A covered porch with a wooden bench, potted plants, and a decorative railing.

4. Wren Retweet- Country Estate in Center of C’Town

Wren Retweet- Country Estate in Center of C’Town
Chestertown
10.0 out of 10, Exceptional, (75 reviews)
"Perfect location for exploring the cutest town. "
United States
Mandy D.
The price is AED 1,182
AED 1,842 total
includes taxes & fees
10 Nov - 11 Nov
Wren Retweet- Country Estate in Center of C’Town
A rooftop terrace with wicker furniture, a fire pit, and a view of a marina.

5. Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
3.0 star property
Grasonville
9.4 out of 10, Exceptional, (847 reviews)
"Awesome place"
United States
Joseph
The price is AED 511
AED 567 total
includes taxes & fees
24 Nov - 25 Nov
Hyatt Place Kent Narrows & Marina
A gazebo with a view of a lake at dusk.

6. 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, (1,004 reviews)
"A wonderful stay! Already planning a trip for next year!"
United States
Michelle
The price is AED 386
AED 428 total
includes taxes & fees
15 Nov - 16 Nov
Holiday Inn Express Annapolis East-Kent Island by IHG
A modern hotel lobby with a long dining table, several chairs, and a bar area.

7. Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South
2.5 star property
Edgewood
9.4 out of 10, Exceptional, (1,007 reviews)
"Just like always a nice quiet place to stay"
United States
Thomas
The price is AED 313
AED 351 total
includes taxes & fees
2 Nov - 3 Nov
Hampton Inn & Suites Edgewood/Aberdeen-South
A Victorian-style building with a porch, outdoor seating, and a sign for Vandiver Inn.

8. Vandiver Inn

Vandiver Inn
3.5 star property
Havre De Grace
9.4 out of 10, Exceptional, (577 reviews)
"A wonderful two nights at the Vandiver Inn! Beds were very comfortable, our room was spacious and the breakfast was outstanding!! I look forward to returning!!"
United States
Mary
The price is AED 642
AED 719 total
includes taxes & fees
2 Nov - 3 Nov
Vandiver Inn
A balcony with a view of a body of water, a row of buildings, and a chair.

9. Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
3.0 star property
Grasonville
9.0 out of 10, Wonderful, (1,002 reviews)
"Great bartender she was a true professional at her job"
United States
Charles
The price is AED 482
AED 534 total
includes taxes & fees
22 Nov - 23 Nov
Hilton Garden Inn Kent Island Marina
A modern kitchen with stainless steel appliances, white cabinetry, and a large window providing a view of greenery.

10. Welcome to the secluded waterfront oasis

Welcome to the secluded waterfront oasis
Millington
8.0 out of 10, Very good, (3 reviews)
"We really enjoyed our stay here! The house was clean, cozy, and had everything we needed. The host was so nice and easy to communicate with, which made everything really easy. We felt right at home and would definitely stay here again!"
United States
Destiny H.
The price is AED 701
AED 1,362 total
includes taxes & fees
28 Oct - 29 Oct
Welcome to the secluded waterfront oasis
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

Pendry Baltimore

Pendry Baltimore

10/10 Excellent
"Beautiful hotel and an incredible location"
Tanner 2-night trip
Posted 1 day ago
Pendry Baltimore
Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

10/10 Excellent
"Easy access to downtown, Great waterside restaurants."
John 1-night trip
Posted 4 days ago
Annapolis Waterfront Hotel, Autograph Collection

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 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.

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