Find pet-friendly hotels in Chestertown, MD from $70

Discover top Chestertown attractions with your pet

Chestertown, Maryland, offers a charming getaway for pet owners who want to explore this historical town while enjoying quality time with their furry friends. Stroll along the scenic Chestertown waterfront, where your dog can join you on the picturesque walking paths lined with quaint shops and cafes, all while soaking in views of the Chester River. Consider a visit to the nearby Wilmer Park, where expansive green spaces allow for leisurely picnics and playful afternoons with your pet. For history enthusiasts, the Chestertown Historic District provides a lovely backdrop with its 18th-century architecture, offering plenty of pet-friendly outdoor areas for exploration. If you're looking for an activity, the Chestertown Farmers Market is a delightful Saturday outing, where you can browse local produce and artisan goods while your pet enjoys the lively atmosphere. For accommodation, consider staying near the downtown area, where several pet-friendly hotels offer convenient access to these attractions and provide amenities like pet beds and treats, ensuring both you and your pet have a comfortable and enjoyable stay.

Find the best pet-friendly hotels in Chestertown

Travelers to Chestertown, Maryland can enjoy a welcoming stay with their pets at these top hotels. Each option provides pet-friendly amenities ensuring a comfortable experience for both guests and their furry companions.

Comfort Inn & Suites Chestertown

• Why it's great for a pet-friendly vacation: Comfort Inn & Suites Chestertown is an ideal choice for travelers looking to bring along their pets, featuring a guest review rating of 8.4. This hotel permits pets and offers essential amenities, ensuring a pleasant stay for both guests and their furry friends. With free breakfast options and service animals allowed, this hotel makes it easy to travel with pets without compromising comfort.
• Other amenities: Guests will appreciate the accessible features including a fitness center, pool, and daily housekeeping. The hotel also provides free internet access, designer toiletries, and microwave facilities for added convenience. Located near historical sites, travelers can enjoy winery tours and explore the charming local area while enjoying the comforts of the hotel.
• Nearby attractions: Rolling Road Park - 0.89 miles, Chestertown Dog Park - 0.95 miles

Driftwood Inn

• Why it's great for a pet-friendly vacation: Driftwood Inn is a charming hotel for travelers wanting to enjoy Chestertown while bringing their pets along. With a review rating of 7.4, this pet-friendly hotel ensures that guests and their furry companions feel right at home. Allowing pets on the premises, it provides a welcoming atmosphere for those traveling with animals.
• Other amenities: Guests can enjoy daily housekeeping, complimentary toiletries, and convenient microwave facilities in their rooms. The hotel also offers free self-parking and features child-friendly window designs, ensuring a safe environment for families. With its cozy ambiance, Driftwood Inn is a delightful choice for pet owners.
• Nearby attractions: Rolling Road Park - 0.62 miles, Chestertown Dog Park - 0.69 miles

Red Roof Inn & Suites Chestertown

• Why it's great for a pet-friendly vacation: Red Roof Inn & Suites Chestertown welcomes pets with open arms, making it a great fit for travelers who want to enjoy a straightforward stay with their dogs and cats. With a review rating of 7.0, this budget-friendly hotel allows pets in rooms and ensures guests have all the essentials for a comfortable visit.
• Other amenities: The hotel features free parking, including options for RVs and buses, as well as air-conditioned rooms. Guests can benefit from daily housekeeping, free long-distance calls, and complimentary toiletries. The presence of a sofa bed and free cribs also enhances the stay for families traveling with pets.
• Nearby attractions: Rolling Road Park - 0.84 miles, Chestertown Dog Park - 0.9 miles