Chestertown Beach Hotels
If You Are in a Hurry
Here’s a quick list of the best hotels in Chestertown
Nestled along the scenic shores of Chestertown, Maryland, the quaint coastal town invites travelers to unwind in its charming beachfront hotels. Offering a perfect blend of relaxation and adventure, these accommodations cater to all tastes—whether you crave luxurious amenities or cozy retreats that echo the sounds of crashing waves. Discover hidden gems and top-rated spots that promise not only breathtaking waterfront views but also a warm embrace of local hospitality, making your stay an unforgettable seaside escape.
Best Hotels on the Beach in Chestertown
Walk to the Beach with Deck, Fireplace, BBQ Grill, Boat Ramp & Office
Walk to the Beach with Deck, Fireplace, BBQ Grill, Boat Ramp & Office is located in Chestertown and features water sports facilities, complimentary bikes, and a bar. Guests can enjoy access to a patio, a pool table, free private parking, and free WiFi. The spacious holiday home includes 5 bedrooms and boasts a flat-screen TV with streaming services along with a fully equipped kitchen that has amenities such as a dishwasher and an oven. Additional conveniences include towels and bed linen provided for guests. A family-friendly restaurant on-site serves American cuisine for lunch and dinner, while the property also offers a picnic area for outdoor enjoyment. New Castle Airport is the nearest airport at 91 km away. - Proximity to the beach - Fully equipped kitchen - Family-friendly dining options - Water sports facilities available - Outdoor picnic area for relaxation
Waterfront Millington Vacation Rental with Hot Tub!
Waterfront Millington Vacation Rental with Hot Tub! is a spacious holiday home located in Millington, just 39 km from Snowland and 40 km from the Delaware State Police Museum and Education Center. This comfortable property features air conditioning, free WiFi, and a cozy fireplace. Accommodating up to 7 bedrooms, it includes a fully equipped kitchen complete with a dishwasher and oven, as well as convenient amenities like towels and bed linen. Guests can also enjoy nearby attractions such as Air Mobility Command Museum, Bohemia Vista Marina, and Dover International Speedway. - Spacious accommodation with 7 bedrooms - Fully equipped kitchen for convenient meal preparation - Relaxing hot tub for ultimate relaxation - Free WiFi available throughout the property - Close proximity to local attractions
Carriage House Hideaway In Center of Chestertown
Carriage House Hideaway is situated in the heart of Chestertown, Maryland, and boasts a charming garden area. This non-smoking accommodation provides a serene getaway for visitors. The nearest airport is New Castle Airport, located 77 km away. - Central location in Chestertown - Peaceful garden setting - Non-smoking environment - Convenient access to nearby amenities - Ideal for relaxation and exploration
Comfort Inn & Suites Chestertown
Comfort Inn & Suites Chestertown is conveniently located less than 1 mile from Washington College and offers free Wi-Fi throughout the property. Each room features a flat-screen TV, microwave, and refrigerator, all decorated in soft colors with dark wood furnishings. Guests can enjoy a hot continental breakfast daily, along with access to an on-site fitness center and business center. Laundry facilities are also available for convenience. For outdoor enthusiasts, the scenic Chester River—ideal for kayaking or canoeing—is just 2 miles away, while Chestertown's charming boutique shops and restaurants are only a 5-minute drive from the hotel. - Proximity to Washington College - Complimentary hot continental breakfast - On-site fitness center and business center - Easy access to kayaking or canoeing on Chester River - Close to boutique shops and restaurants
Family-Friendly Cottage, Walk to the Beach!
Family-Friendly Cottage, Walk to the Beach! offers a delightful stay in Kennedyville with free bikes and complimentary WiFi. This charming holiday home features two bedrooms, a flat-screen TV, and a fully equipped kitchen complete with modern appliances such as a dishwasher, oven, washing machine, microwave, and toaster. Guests will find towels and bed linen provided for their convenience. A cozy fireplace adds to the inviting atmosphere of this retreat. Located 63 km from New Castle Airport and within reach of Bohemia Vista Marina at 35 km away. - Close proximity to the beach - Fully equipped kitchen for convenient meal preparation - Free bikes available for guests - Cozy fireplace enhancing the homey feel - Free WiFi throughout the property
Eastern Shore Getaway Walk to Tolchester Marina!
Eastern Shore Getaway Walk to Tolchester Marina! is a spacious holiday home located in Rock Hall, offering air-conditioned accommodation complete with a balcony and free WiFi. This well-equipped property features 5 bedrooms, a flat-screen TV with cable channels, and a fully equipped kitchen including modern appliances such as a microwave, toaster, washing machine, and fridge. Guests can enjoy the comfort of towels and bed linen provided, along with access to on-site parking and complimentary bicycles for exploring the area. The holiday home also boasts a cozy fireplace and an on-site bar for relaxation. - Free use of bicycles for exploring - Spacious living area with 5 bedrooms - Fully equipped kitchen with essential appliances - On-site parking available - Close proximity to Tolchester Marina
Driftwood Inn
Driftwood Inn is a convenient motel located just a 6-minute walk from Washington College and 2 miles from downtown Chestertown, Maryland. Guests can enjoy complimentary Wi-Fi and access to a 24-hour front desk during their stay. The rooms feature rustic wood paneling with soft neutral colors, equipped with cable TV offering HBO channels, microwaves, and refrigerators. Additional amenities include coffee in the lobby, vending machines for drinks, and copy and fax services available at the front desk. The Chester River Yacht and Country Club is just 2.5 miles away, while Remington Farms National Wildlife Preserve can be reached within a 14-minute drive. - Proximity to Washington College - Free Wi-Fi available - Rustic room decor with modern amenities - Convenient on-site services (copy/fax) - Close to recreational areas like yacht club and wildlife preserve