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

Find Pet-friendly Hotels in Chestertown, MD

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check availability on Chestertown Pet-friendly Hotels

Tonight
9 Sep - 10 Sep
Tomorrow
10 Sep - 11 Sep
This weekend
11 Sep - 13 Sep
Next weekend
18 Sep - 20 Sep

Our top choices for Chestertown pet-friendly hotels

Free daily full breakfast
Lobby
Desk, laptop workspace, blackout drapes, iron/ironing board
Point of interest

1. Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
Chestertown
United States
Amy
AED 381
AED 423 total
includes taxes & fees
4 Oct - 5 Oct
Comfort Inn & Suites Chestertown
Exterior
Desk, laptop workspace, blackout drapes, iron/ironing board
Exterior
Lobby lounge

2. Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
Chestertown
United States
Linda
AED 264
AED 294 total
includes taxes & fees
15 Sep - 16 Sep
Red Roof Inn & Suites Chestertown
Front of property - evening/night
TV
Room | Desk, soundproofing, WiFi (free), bed sheets
Front of property

3. Driftwood Inn

Driftwood Inn
Chestertown
United States
Kathy
AED 233
AED 259 total
includes taxes & fees
11 Sep - 12 Sep
Driftwood Inn
Property grounds
5 bedrooms, desk, iron/ironing board, WiFi (free)
Interior
Exterior detail

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
14 Sep - 15 Sep
Wren Retweet- Country Estate in Center of C’Town
Exterior
Standard Room, 1 King Bed, River View | Premium bedding, in-room safe, desk, iron/ironing board
Exterior
Exterior

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

Holiday Inn Express Annapolis East-Kent Island by IHG
Grasonville
United States
Emily
AED 466
AED 518 total
includes taxes & fees
5 Oct - 6 Oct
Holiday Inn Express Annapolis East-Kent Island by IHG
Terrace/patio
Free daily buffet breakfast
Suite, 1 Queen Bed | Living area | 50-inch flat-screen TV with cable channels, TV
Exterior

6. Home2 Suites by Hilton Baltimore / Aberdeen, MD

Home2 Suites by Hilton Baltimore / Aberdeen, MD
Aberdeen
United States
Eileen
AED 373
AED 418 total
includes taxes & fees
20 Sep - 21 Sep
Home2 Suites by Hilton Baltimore / Aberdeen, MD
Standard Room, 1 Queen Bed, Non Smoking, Refrigerator & Microwave | In-room safe, desk, laptop workspace, iron/ironing board
Lobby
Indoor pool
Property amenity

7. Best Western Kent Narrows Inn

Best Western Kent Narrows Inn
Grasonville
United States
Joshua
AED 393
AED 437 total
includes taxes & fees
15 Sep - 16 Sep
Best Western Kent Narrows Inn
Reception
Pool
Reception
King suite whirlpool | Bathroom | Combined shower/tub, free toiletries, hair dryer, towels

8. Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South
Edgewood
United States
walter
AED 310
AED 347 total
includes taxes & fees
29 Sep - 30 Sep
Hampton Inn & Suites Edgewood/Aberdeen-South
Terrace/patio
Exterior
Lobby
Marina

9. Hyatt Place Kent Narrows & Marina

Hyatt Place Kent Narrows & Marina
Grasonville
United States
Karen
AED 558
AED 620 total
includes taxes & fees
4 Oct - 5 Oct
Hyatt Place Kent Narrows & Marina
Terrace/patio
Indoor pool, open 5 AM to 11 PM, sun loungers
Restaurant
Exterior

10. Hilton Garden Inn Kent Island Marina

Hilton Garden Inn Kent Island Marina
Grasonville
United States
roney
AED 539
AED 598 total
includes taxes & fees
4 Oct - 5 Oct
Hilton Garden Inn Kent Island Marina
View all properties

Top Chestertown Hotel Reviews

Pendry Baltimore

Pendry Baltimore

10/10 Excellent
"Balcony was a great option! Water Taxi excursion added to the trip!"
mary 2-night trip
Posted 2 days ago
Pendry Baltimore

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

Explore a world of travel with Expedia