Chestertown Beach Hotels


If You Are in a Hurry

Here’s a quick list of the best hotels in Chestertown

Carriage House Hideaway In Center of Chestertown
Carriage House Hideaway In Center of Chestertown
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Comfort Inn & Suites Chestertown
Comfort Inn & Suites Chestertown
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Eastern Shore Getaway Walk to Tolchester Marina!
Eastern Shore Getaway Walk to Tolchester Marina!
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Driftwood Inn
Driftwood Inn
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Family-Friendly Cottage, Walk to the Beach!
Family-Friendly Cottage, Walk to the Beach!
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Nestled along the serene shores of the Chester River, Chestertown offers a delightful escape for beach lovers seeking both relaxation and adventure. With a selection of charming hotels that provide stunning waterfront views and easy access to sandy beaches, visitors can savor leisurely mornings by the sea and invigorating afternoons exploring local attractions. From quaint inns with cozy atmospheres to luxurious resorts boasting top-notch amenities, there's an ideal beachfront haven waiting for everyone in this picturesque town.

Best Hotels on the Beach in Chestertown

Carriage House Hideaway In Center of Chestertown

Carriage House Hideaway In Center of Chestertown

Carriage House Hideaway, located in the heart of Chestertown, Maryland, offers a serene garden setting for guests seeking a peaceful retreat. This non-smoking accommodation ensures a comfortable stay, while its proximity to local attractions enhances the overall experience. The nearest airport is New Castle Airport, situated 77 km away. - Central location in Chestertown - Peaceful garden setting - Non-smoking accommodation - Close to local attractions - Convenient access to New Castle Airport

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Comfort Inn & Suites Chestertown

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 adorned with soothing colors and dark wood furnishings. Guests can enjoy a daily hot continental breakfast and have access to on-site fitness and business centers, as well as laundry facilities. The scenic Chester River, ideal for kayaking or canoeing, is just 2 miles away, while the charming boutiques and restaurants of Chestertown’s center are only a 5-minute drive from the hotel. - Close proximity to Washington College - Complimentary hot continental breakfast - On-site fitness center available - Scenic outdoor activities nearby - Variety of dining options within minutes

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Eastern Shore Getaway Walk to Tolchester Marina!

Eastern Shore Getaway Walk to Tolchester Marina!

Eastern Shore Getaway Walk to Tolchester Marina! is a charming holiday home located in Rock Hall, featuring air-conditioned accommodations with a balcony and complimentary WiFi. This spacious property includes five bedrooms, a flat-screen TV with cable channels, and a fully equipped kitchen complete with modern appliances. Guests can enjoy the outdoor space on the patio or take advantage of the free bicycles for exploring the area. On-site parking is available for convenience, and there’s a bar to unwind after an exciting day. - Close proximity to Tolchester Marina - Fully equipped kitchen with modern amenities - Free use of bicycles for local exploration - Spacious accommodations ideal for families or groups - On-site parking available

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Driftwood Inn

Driftwood Inn

Driftwood Inn is conveniently situated just a 6-minute walk from Washington College and offers complimentary Wi-Fi along with a 24-hour front desk service. Located 2 miles from downtown Chestertown, Maryland, the motel features rooms adorned with rustic wood paneling and soft neutral hues, equipped with cable TV featuring HBO channels, microwaves, and refrigerators. Guests can enjoy coffee in the lobby and access vending machines for drinks. Additionally, the Driftwood Inn provides copy and fax services 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. - Walking distance to Washington College - Free Wi-Fi available - Rustic decor for a cozy ambiance - Convenient access to local attractions - Vending machines for snacks and drinks

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Family-Friendly Cottage, Walk to the Beach!

Family-Friendly Cottage, Walk to the Beach!

Family-Friendly Cottage, Walk to the Beach! offers a welcoming stay in Kennedyville with amenities such as free bikes and complimentary WiFi. This holiday home features 2 bedrooms, a flat-screen TV, and a fully equipped kitchen complete with modern appliances like a dishwasher, oven, washing machine, microwave, and toaster. Guests can enjoy the comfort of having towels and bed linen provided as well as the cozy ambiance created by the fireplace. The property is located 35 km from Bohemia Vista Marina and 63 km from New Castle Airport. - Close proximity to the beach - Fully equipped kitchen for convenient meals - Free WiFi throughout the property - Family-friendly atmosphere - Offers free bike rentals for exploring

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Walk to the Beach with Deck, Fireplace, BBQ Grill, Boat Ramp & Office

Walk to the Beach with Deck, Fireplace, BBQ Grill, Boat Ramp & Office

Walk to the Beach with Deck, Fireplace, BBQ Grill, Boat Ramp & Office in Chestertown offers a delightful getaway featuring water sports facilities, complimentary bikes, and an on-site bar. Guests can enjoy access to a patio and a pool table while benefiting from free private parking and WiFi. The spacious holiday home includes 5 bedrooms, a flat-screen TV with streaming services, and a fully equipped kitchen complete with modern appliances such as a dishwasher and washing machine. Additional amenities include a seating area by the fireplace and dining options at the family-friendly restaurant serving American cuisine. A picnic area is also available for outdoor fun. - Close proximity to the beach - Spacious accommodation with modern amenities - On-site dining options serving American cuisine - Access to recreational facilities including water sports - Family-friendly environment with picnic areas

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Waterfront Millington Vacation Rental with Hot Tub!

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. The property features air conditioning, free WiFi, and a fireplace for added comfort. With 7 bedrooms, it includes a fully equipped kitchen complete with a dishwasher and oven, along with provided towels and bed linen. Guests can enjoy proximity to various attractions such as Air Mobility Command Museum (40 km), Bohemia Vista Marina (41 km), Saulsbury Road Park (41 km), and Dover International Speedway (42 km). New Castle Airport is the nearest airport at 63 km away. **Pros:** - Spacious holiday home with 7 bedrooms. - Fully equipped kitchen for convenient meal preparation. - Relaxing hot tub available. - Free WiFi throughout the property. - Close to various local attractions.

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FAQ

"What are the best hotels on the beach in Chestertown?"

"While Chestertown is not directly on the beach, nearby towns like Rock Hall and Betterton offer charming waterfront accommodations. Popular options include The Inn at Huntingfield Creek and The Beach Club at Rock Hall, providing comfortable stays with picturesque views of the Chesapeake Bay."

"Are there any budget-friendly beach hotels in Chestertown?"

"Yes, there are several budget-friendly options near Chestertown that provide easy access to beach areas. Hotels like The Haven Hotel in Rock Hall offer reasonable rates without compromising on comfort or amenities while ensuring you're close to beautiful waterfronts."

"What amenities can I expect from beachfront hotels near Chestertown?"

"Beachfront hotels around Chestertown typically provide a variety of amenities such as free Wi-Fi, complimentary breakfast, pools, outdoor seating areas, and direct access to beaches. Many also have water sports equipment rentals available for guests looking to enjoy activities like kayaking or paddleboarding."

"Is it safe for families to stay at beach hotels near Chestertown?"

"Absolutely! Family-friendly beachfront hotels around Chestertown often prioritize safety and provide suitable accommodations for children. These locations usually have lifeguards during peak season and organized activities tailored towards families so everyone can enjoy a fun yet safe experience by the water."

"When is the best time to book a hotel on the beach near Chestertown?"

"The best time to book a hotel on or near the beach in this area is during late spring or early fall when you can find great deals and fewer crowds. However, summer months are peak season due to warm weather

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