Find hotels in Chestertown, MD from CA $86

Top reasons to visit Chestertown

• Scenic Outdoor Adventures: Experience beautiful landscapes and recreational activities along the picturesque Chester River.
• Charming Downtown: Stroll along Main Street to discover delightful shops and local attractions.
• Rich Historical Experience: Explore the town's rich heritage through house tours and historic sites.
• Festive Community Events: Enjoy lively holiday activities and festivals that showcase the warmth of the community.
• Diverse Accommodation Options: Find a range of pet-friendly and welcoming stays for all types of travellers.

Find great hotels near Chestertown

Explore a variety of accommodation options in Chestertown, Maryland, where you can find pet-friendly hotels and motels, perfect for business travellers and those seeking an LGBTQIA welcoming environment. Whether you're looking for vacation rentals, suites, or house rentals, Chestertown offers a range of choices to ensure a comfortable and enjoyable stay in this charming riverside town.

• Quality Inn & Suites Bel Air I-95 Exit 77A: A prime choice for business travellers, Quality Inn & Suites Bel Air I-95 Exit 77A combines convenience and professionalism. Located 33.8km from Chestertown, this hotel offers an array of amenities designed to cater to business needs, such as meeting rooms, free Wi-Fi, and a business centre. Guests have praised the comfortable rooms, ideal for unwinding after a busy day of meetings, along with complimentary breakfast options to kickstart their mornings. Its strategic location near major highways makes it an excellent stop for those on the go.
• La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A: This welcoming hotel, situated 33.8km from Chestertown, is a haven for pet owners and travellers seeking relaxation. La Quinta Inn & Suites features a pet-friendly policy, allowing dogs and cats to stay with their owners, making it perfect for those travelling with furry friends. Guests appreciate the spacious rooms and complimentary breakfast, which provides a delightful start to their day. The hotel also boasts a convenient location near local attractions and dining options, ensuring an enjoyable and hassle-free stay for all.
• Red Roof Inn Aberdeen: Located 35.4km from Chestertown, Red Roof Inn Aberdeen is a vibrant option for pet-lovers and LGBTQIA-friendly travellers. This hotel not only welcomes pets but also supports an inclusive environment, making it a comfortable choice for all guests. With amenities that allow pets in rooms and a waived fee for service animals, it’s designed with comfort in mind. Guests have highlighted the affordable rates, clean accommodations, and friendly staff, making it a popular choice for those looking for a welcoming getaway.

Where to stay in and around Chestertown

Chestertown, Maryland, offers a delightful blend of outdoor adventures and rich history, perfect for a family-friendly getaway. Explore charming neighbourhoods and discover friendly resorts that capture the essence of hometown holidays. Enjoy the scenic beauty while soaking in the historical atmosphere, making it an ideal destination for a relaxing weekend escape. Experience the warmth of the community during the holiday season and uncover the hidden gems that make Chestertown a must-visit spot.

• Worton: Located a mere 6.4km from Chestertown, Worton offers a charming escape for those seeking outdoor adventures and stunning scenery. While the number of visitors fluctuates throughout the year, the peak seasons in April to May and July draw in nature enthusiasts eager to explore its recreational areas and nearby national parks. With attractions such as beautiful beaches and marinas, Worton is perfect for a leisurely day of exploration or fun-filled activities on the water.
• Georgetown: Nestled in the vicinity of Chestertown, Georgetown is a quaint village that captivates visitors with its romantic outdoor settings and adventurous spirit. The peak tourist months from June to August offer a lively atmosphere, where you can engage in various recreational activities or relax at local recreation centres. Notable landmarks like sports facilities and a stadium enhance the area’s appeal, making it an excellent spot for those looking to combine relaxation with a dash of excitement.
• Tolchester Beach: As a delightful village close to Chestertown, Tolchester Beach is an ideal destination for beach lovers and those yearning for natural beauty. While it experiences consistent visitor numbers throughout the year, summer months from June to August are particularly popular. Enjoy leisurely strolls along the boardwalk or take advantage of the recreational areas and nearby marinas. With its proximity to national parks and serene beaches, Tolchester Beach promises a refreshing getaway filled with outdoor enjoyment.

Things to do in and around Chestertown

Chestertown, Maryland, is perfect for an outdoor getaway, offering beautiful scenery and a range of activities. Visitors can enjoy house tours, explore recreational areas, stroll along the boardwalk, and participate in festival events. The downtown area hosts festive holiday activities, making it an ideal spot for a weekend escape or day trip, ensuring a delightful experience for all who visit.

Shopping

In Chestertown, you can enjoy local shops and boutiques for unique gifts. If you're up for a drive, visit the Queenstown Premium Outlets, located 27.4km away, for brand-name bargains. Paul Reed Smith Guitars, 33.8km away, offers a unique shopping experience for music enthusiasts.

Recreation

At Ripken Stadium, you can immerse yourself in the vibrant sports atmosphere while enjoying various recreational events. Meanwhile, the Queenstown Harbor Golf Club and Queenstown Harbor Golf Links offer beautiful outdoor settings for a relaxing yet active day on the greens, surrounded by nature's beauty.

Adventure

At the Annapolis Sailing School, located 45.1km from Chestertown, you can immerse yourself in thrilling sailing experiences on the beautiful Chesapeake Bay. Alternatively, the Emmorton Recreation & Tennis Center, 38.6km away, offers various engaging recreational activities, while the Tose Family Tennis Center, also 45.1km away, boasts fantastic tennis facilities.

Nightlife

In Chestertown, the Garfield Center for the Arts at the Prince Theater offers vibrant performances in a charming atmosphere. Just a short drive away, Church Hill Theatre and Avalon Theatre also provide engaging shows, each with a touch of culture and romance, perfect for a delightful evening out.

Booking tips and Expedia advantages for Chestertown

For a budget-friendly trip to Chestertown, consider visiting between January to February or November for lower accommodation rates. Tuesdays are the cheapest days to stay, while Saturdays tend to be pricier. Use Expedia’s search tool to find budget options, including eco-friendly hotels, and filter by price to uncover the best deals. Additionally, you can save money by bundling your hotel, flights, and activities into an Expedia package. Don’t forget to explore free local attractions to enhance your experience while keeping costs down.

• The most and least expensive months on average to stay in a hotel: The cheapest months to stay in Chestertown are January to February and November, where the prices are slightly lower. This is in comparison to June to July and October, where prices are slightly higher.
• The most and least expensive days on average to stay in a hotel: The least expensive day to stay in Chestertown is Tuesday. The most expensive day to stay in Chestertown is Saturday.
• Find cheap hotels on Expedia: Utilize Expedia’s search tool to customize your travel preferences, such as your budget, desired location, and preferred type of accommodation. For instance, selecting the Eco-certified option will showcase sustainable and environmentally-friendly hotels that are currently available. To find the best prices and deals, simply sort the price filter from lowest to highest.
• Consider bundling your trip: You can save some money by combining your Chestertown hotel reservation with your flights and activities through an Expedia package.

Find the best attractions in Chestertown

Chestertown, Maryland, offers a delightful mix of outdoor adventures and scenic beauty, perfect for a family beach vacation. Visitors can explore urban parks, marinas, and the picturesque Chester River. A stroll down Main Street Chestertown reveals charming shops and local attractions, making it an ideal destination for those seeking a relaxing getaway in nature.

• Washington College: Experience the charm of this historic institution, renowned for its picturesque campus and rich cultural heritage. Engage in various events, art exhibitions, and lectures that showcase the vibrant academic community.
• Rolphs Wharf Marina: Dive into outdoor adventures at this scenic marina. Enjoy kayaking, paddleboarding, or simply relaxing by the water's edge, surrounded by beautiful beach vibes and stunning views of the Chester River.
• Historical Society of Kent County Maryland: Discover the local history at this engaging museum. Explore fascinating exhibits that highlight the region's past, offering insight into the culture and traditions of Kent County.

Best time to go to Chestertown

The best time to visit Chestertown is dependant on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are slightly low and weather is mostly sunny with light rain.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	34.2°F (1.2°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly Low
February	36.9°F (2.7°C)	Light Rain	Mostly Sunny	Average	Slightly Low
March	43.7°F (6.5°C)	Light Rain	Mostly Sunny	Average	Average
April	54.3°F (12.4°C)	Light Rain	Mostly Sunny	Slightly High	Average
May	63.7°F (17.6°C)	Light Rain	Mostly Sunny	Average	Average
June	72.1°F (22.3°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
July	77.4°F (25.2°C)	Light Rain	Mostly Sunny	Slightly High	Slightly High
August	75.6°F (24.2°C)	Light Rain	Mostly Sunny	Average	Average
September	69.4°F (20.8°C)	Light Rain	Mostly Sunny	Average	Average
October	59.2°F (15.1°C)	Light Rain	Mostly Sunny	Average	Slightly High
November	47.3°F (8.5°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly Low
December	40.1°F (4.5°C)	Light Rain	Mostly Sunny	Slightly Low	Average

The nearest major airports for your trip to Chestertown

Chestertown, Maryland, can be conveniently accessed via three major airports. Washington, DC (DCA-Ronald Reagan Washington National) is located 93.3km away, with notable hotels like the 5-star InterContinental Washington D.C. - The Wharf and Riggs Washington DC, both within 4.8km. Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall) is closer at 51.5km, featuring luxurious options such as the Sagamore Pendry Baltimore and Four Seasons Hotel Baltimore, both 12.9km from the airport, offering shuttle services. Lastly, Baltimore, MD (MTN-Martin State) lies 32.2km away, with hotels like Canopy by Hilton Baltimore Harbor Point and Hyatt Place Baltimore Inner Harbor, both around 16.1km from the airport.