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

Find Pet-friendly Hotels in Chestertown, MD

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Check availability on Chestertown Pet-friendly Hotels

Tonight
24 Sep - 25 Sep
Tomorrow
25 Sep - 26 Sep
This weekend
25 Sep - 27 Sep
Next weekend
2 Oct - 4 Oct

Our top choices for Chestertown pet-friendly hotels

1. Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
Chestertown
United States
Amy
AED 379
AED 421 total
includes taxes & fees
25 Oct - 26 Oct
Comfort Inn & Suites Chestertown

2. Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
Chestertown
United States
Linda
AED 264
AED 294 total
includes taxes & fees
30 Sep - 1 Oct
Red Roof Inn & Suites Chestertown

3. Driftwood Inn

Driftwood Inn
Chestertown
United States
Kathy
AED 233
AED 259 total
includes taxes & fees
27 Sep - 28 Sep
Driftwood Inn

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

Wren Retweet- Country Estate in Center of C’Town
Chestertown
United States
Mandy D.
AED 1,119
AED 1,768 total
includes taxes & fees
27 Sep - 28 Sep
Wren Retweet- Country Estate in Center of C’Town

5. Holiday Inn Express Annapolis East-Kent Island by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG
Grasonville
United States
Marc
AED 378
AED 420 total
includes taxes & fees
25 Oct - 26 Oct
Holiday Inn Express Annapolis East-Kent Island by IHG

6. Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
Grasonville
United States
Joshua
AED 427
AED 474 total
includes taxes & fees
30 Sep - 1 Oct
Best Western Kent Narrows Inn

7. Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South
Edgewood
United States
walter
AED 313
AED 351 total
includes taxes & fees
30 Sep - 1 Oct
Hampton Inn & Suites Edgewood/Aberdeen-South

8. Bayside Cottage steps from Rock Hall Harbor

Bayside Cottage steps from Rock Hall Harbor
Rock Hall
United States
Adam S.
AED 713
AED 1,421 total
includes taxes & fees
27 Sep - 28 Sep
Bayside Cottage steps from Rock Hall Harbor

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

La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A
Edgewood
United States
Jenri
AED 290
AED 325 total
includes taxes & fees
27 Sep - 28 Sep
La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

10. Hilton Garden Inn Aberdeen

Hilton Garden Inn Aberdeen
Aberdeen
United States
Philip
AED 404
AED 452 total
includes taxes & fees
1 Oct - 2 Oct
Hilton Garden Inn Aberdeen
View all properties

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
"room was clean, and the breakfast was as expected. The only bad thing was that treadmill in the gym was out of service, which I found disappointing."
Steven 1-night trip
Posted 13 hours ago
La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A
Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

8/10 Good
"The view from our room was incredible. The property is clean and the beds comfortable. For the price, however, the only thing that justifies it is the view and location. There are 2 restaurants- Marmo was disappointing and overpriced. The cantina was great. Unfortunately, they take up all of the waterfront dock area, so there is really nowhere else to gather in the hotel to enjoy the water if you just want to sit and visit or play a game, or some such. (The balconies were too small for anything except a cup of coffee). And since the restaurants are open to the public the area is packed all the time. Otherwise, being an older hotel, there really aren't any special amenities. No spa or pool. nothing else special about it. And those terrible nespresso machines in the room. I just want a regular cup of coffee. Parking is overpriced- we hoofed it to a garage a few blocks away for significantly less per day."
Karen 3-night trip
Posted 2 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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