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

Pet Friendly Hotels & Resorts in Chestertown from AU$88

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check availability on Chestertown Pet Friendly Hotels

Our top choices for Chestertown pet-friendly hotels

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
2.5 star property
Chestertown
8.6 out of 10, Excellent, (926 reviews)
"Great visit"
United States
Danielle
The price is AU$163
includes taxes & fees
19 July - 20 July
Comfort Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
2.0 star property
Chestertown
7.2 out of 10, Good, (457 reviews)
"Perfect for an overnight trip, staff was very helpful."
United States
Anasmel
The price is AU$114
includes taxes & fees
28 June - 29 June
Red Roof Inn & Suites Chestertown

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 AU$100
includes taxes & fees
29 June - 30 June
Driftwood Inn

Historic Inns of Annapolis

Historic Inns of Annapolis
3.5 star property
Historic District
9.0 out of 10, Wonderful, (1,856 reviews)
"Great hotel..will definitely be back"
United States
Randy
The price is AU$214
includes taxes & fees
19 July - 20 July
Historic Inns of Annapolis

Vandiver Inn

Vandiver Inn
3.5 star property
Havre De Grace
9.4 out of 10, Exceptional, (554 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 AU$231
includes taxes & fees
25 June - 26 June
Vandiver Inn

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, (1,003 reviews)
"Great place to stay"
United States
Harry
The price is AU$144
includes taxes & fees
7 July - 8 July
La Quinta Inn & Suites by Wyndham Aberdeen-APG

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, (17 reviews)
"Nice place"
United States
christine
The price is AU$131
includes taxes & fees
21 June - 22 June
Charming 2-bedroom house in Aberdeen with WiFi and AC

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)
"Good hotel for the price"
United States
Brenda
The price is AU$173
includes taxes & fees
6 July - 7 July
Best Western Kent Narrows Inn

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, (382 reviews)
"Great stay at this"
United States
Wilson
The price is AU$156
includes taxes & fees
28 June - 29 June
Home2 Suites by Hilton Baltimore / Aberdeen, MD

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, (1,000 reviews)
"Beautiful view!!! Clean hotel and very nice helpful staff. Would stay again."
United States
Michele
The price is AU$198
includes taxes & fees
6 July - 7 July
Holiday Inn Express Annapolis East-Kent Island by IHG
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.

Top Chestertown Hotel Reviews

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.