Chester Hotels

Top reasons to visit Chester

• Scenic Boardwalk: Enjoy leisurely strolls along Chester's picturesque boardwalk, perfect for romantic evenings and family outings.
• Outdoor Adventures: Experience a variety of outdoor activities, including golfing, hiking in national parks, and exploring urban parks.
• Cultural Experiences: Discover local culture through city attractions and historical sites, enriching your visit.
• Vibrant Nightlife: Unwind at charming eateries and bars, enjoying the lively atmosphere after a day of exploration.
• Diverse Accommodation: Choose from a range of options, including cosy bed and breakfasts and modern hotels tailored to your needs.

Find great hotels near Chester

Chester, Maryland offers a delightful selection of accommodation options, ranging from charming bed and breakfasts to well-equipped hotels. Whether you're travelling with family, on a business trip, or seeking a pet-friendly retreat, you'll find a variety of hotels tailored to your needs. Explore the best Chester hotels and read reviews to discover the perfect place for your stay in this picturesque area.

• Country Inn & Suites by Radisson, Annapolis, MD: A welcoming haven for all travellers, Country Inn & Suites by Radisson, Annapolis, MD, is a charming 3-star hotel located 22.5km from Chester. With a strong commitment to inclusivity, this property is particularly suited for LGBTQIA guests and those travelling with pets. Guests can enjoy a range of amenities, including a designated dog exercise area and special pet policies. The hotel also caters to business travellers, ensuring a comfortable and productive stay. Its friendly atmosphere and practical offerings make it an ideal choice for a relaxing getaway.
• Historic Inns of Annapolis: Nestled within a national historic building, the Historic Inns of Annapolis offers a unique blend of charm and history, just 17.7km from Chester. This 3.5-star hotel is perfect for guests seeking a taste of the past while enjoying modern conveniences. Its historic theme creates an enchanting atmosphere, and the property is well-suited for business travellers looking for a distinctive experience. Guests appreciate the elegant decor and the sense of stepping back in time, making it an unforgettable stay.
• Graduate by Hilton Annapolis: Situated 17.7km from Chester, Graduate by Hilton Annapolis is a stylish 4-star hotel that caters to families and business travellers alike. This welcoming establishment prides itself on being LGBTQIA-friendly and offers amenities specifically designed for children, such as free cribs. The hotel's contemporary design is complemented by a warm and inviting atmosphere, making it an excellent choice for those seeking comfort and convenience. With its thoughtful services and family-friendly features, a delightful stay awaits at the Graduate.

Where to stay near Chester

Chester, Maryland, offers a delightful blend of outdoor adventures and romantic beach getaways, perfect for a memorable escape. Visitors can bask in the sunny weather while exploring family-friendly attractions and historical sites. Nearby regions on the Eastern Shore provide a welcoming atmosphere with friendly locals, making it an ideal destination for both relaxation and discovery. Whether you're seeking a charming family holiday or a peaceful retreat, Chester promises an enriching travel experience.

• Annapolis: Located 17.7km from Chester, Annapolis is a historic city known for its charming waterfront and vibrant atmosphere. Visitors can immerse themselves in the rich maritime heritage and explore the iconic Naval Academy. The city is bustling with a variety of shopping centres and malls, making it a great destination for retail therapy. From June to August, Annapolis sees a peak in visitors, drawn by its family-friendly activities and business-themed events. Notable attractions include local beaches and the picturesque tourist precinct, perfect for leisurely strolls and educational experiences.
• Stevensville: Just 1.6km away from Chester, Stevensville is a delightful city that beckons outdoor enthusiasts and adventure seekers. With its scenic landscapes and proximity to the Chesapeake Bay, visitors can enjoy activities ranging from nature walks to exploring the local boardwalk and recreational areas. The peak travel times in April and June to July offer a chance to experience the area's natural beauty and family-oriented attractions, including nearby beaches and a national state park. Stevensville is the ideal spot for those looking to reconnect with nature while enjoying a relaxed atmosphere.
• Kent Narrows: This charming village, located 4.8km from Chester, is a popular destination for families and couples seeking outdoor adventures. Kent Narrows features a lovely boardwalk and shopping centres, providing a perfect blend of relaxation and retail enjoyment. The village is particularly lively from June to August, attracting visitors with its romantic settings and family-friendly activities. Highlights include the picturesque esplanade and beautiful beaches, making it a wonderful place to unwind and explore the local tourist precinct.

Things to do near Chester

Chester, Maryland, offers a delightful blend of outdoor and romantic experiences, ideal for a beach vacation. Visitors can enjoy the scenic boardwalk, engage in educational activities, and play a round of golf. For a taste of local culture, explore city experiences and best attractions, while the nightlife promises a vibrant atmosphere with charming eateries and bars to unwind after a day of exploration.

Shopping

In Chester, visit Paul Reed Smith Guitars, just 3.2km away, for unique musical souvenirs. Alternatively, Queenstown Premium Outlets, located 11.3km away, offers a variety of shopping options in a vibrant atmosphere. If you're up for a drive, the Annapolis Harbour Center is 22.5km away, providing a lively shopping experience.

Recreation

Navy-Marine Corps Memorial Stadium, located 19.3km from Chester, offers a vibrant sports atmosphere perfect for energising activities. Queenstown Harbor Golf Club, just 11.3km away, provides a picturesque outdoor golfing experience. For a touch of culture, Ballet Theater of Maryland, also 19.3km distant, showcases enchanting dance performances.

Adventure

St Michaels Nature Trail offers a scenic outdoor experience, perfect for hiking enthusiasts, located 20.9km from Chester. For a splash of fun, visit Chesapeake Beach Water Park, 38.6km away, featuring thrilling rides for families. Alternatively, enjoy the excitement of sailing at Annapolis Sailing School, 16.1km from Chester.

Nightlife

In Chester, the Church Hill Theatre offers a romantic cultural experience, while The Colonial Players provide a similar atmosphere just 17.7km away. For family fun, the Annapolis Bowl arcade, located 22.5km from Chester, promises adventurous entertainment for all ages.

Booking tips and Expedia advantages for Chester

For a budget-friendly visit to Chester, consider travelling during the off-peak months of December to February, when accommodation prices are lower. Booking on a Monday can also save you money, while Saturday stays tend to be pricier. Use Expedia’s search tool to filter options by budget and eco-certification for sustainable stays. Combine your hotel, flights, and activities in a package to secure better deals. Additionally, keep an eye out for discounts on beverages and other promotions to maximise your savings while exploring Chester.

• The most and least expensive months on average to stay in a hotel: The cheapest months to stay in Chester are December to February, where the prices are slightly lower. This is in comparison to May and September to 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 Chester is Monday. The most expensive day to stay in Chester is Saturday.
• Find cheap hotels on Expedia: Utilise Expedia’s search tool to refine your preferences, such as your budget, preferred location, and the type of accommodation you desire. For instance, selecting the Eco-certified option will showcase sustainable and environmentally friendly hotels currently available. To find the most affordable prices and offers, arrange the price filter from low to high.
• Consider bundling your trip: You can save money by combining your Chester hotel accommodation with your flights and activities through an Expedia package.

Find the best attractions near Chester

Chester, Maryland, is an idyllic destination for outdoor and romantic beach vacations, offering a variety of attractions such as urban parks, marinas, and national state parks. Visitors can enjoy a blend of outdoor activities, cultural experiences, and family-friendly options. For a comprehensive experience, consider exploring nearby attractions and the best resorts to enhance your stay in this charming locale.

• Chesapeake Bay Bridge: This impressive modern bridge spans the Chesapeake Bay, offering stunning views and a unique experience of crossing this iconic structure. The bridge connects the Eastern Shore to the mainland and provides a glimpse into the vibrant city life of the area.
• Sandy Point State Park: Nestled alongside the bay, this national park is perfect for outdoor enthusiasts. Enjoy beautiful scenery, sandy beaches, and a variety of adventure activities such as hiking, picnicking, and birdwatching amidst the natural beauty of the region.
• Maryland State House: As the oldest state capitol still in continuous use, this historic building is rich in culture and heritage. Explore its stunning architecture and learn about Maryland’s history, making it a must-visit for history buffs.

Best time to go to Chester

The best time to visit Chester can depend on the weather and when visitor numbers rise and fall. The hottest average temperature in Chester falls in July, when visitor numbers are slightly high and weather is mostly sunny with light rain. The coolest average temperature in Chester falls in January, visitor numbers are slightly low and weather is mostly sunny with light rain.

Calendar Month	Temperature	Precipitation	Cloudiness	Occupancy	Pricing
January	35.1°F (1.7°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly Low
February	37.4°F (3.0°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly Low
March	43.9°F (6.6°C)	Light Rain	Mostly Sunny	Average	Average
April	54.1°F (12.3°C)	Light Rain	Mostly Sunny	Average	Average
May	63.5°F (17.5°C)	Light Rain	Mostly Sunny	Average	Slightly High
June	72.3°F (22.4°C)	Light Rain	Mostly Sunny	Slightly High	Average
July	77.9°F (25.5°C)	Light Rain	Mostly Sunny	Slightly High	Average
August	76.3°F (24.6°C)	Light Rain	Mostly Sunny	Slightly High	Average
September	70.5°F (21.4°C)	Light Rain	Mostly Sunny	Average	Slightly High
October	60.3°F (15.7°C)	Light Rain	Mostly Sunny	Average	Slightly High
November	48.7°F (9.3°C)	Light Rain	Mostly Sunny	Average	Average
December	41.0°F (5.0°C)	Light Rain	Mostly Sunny	Slightly Low	Slightly Low

The nearest major airports for your trip to Chester

Travelling to Chester, Maryland, is convenient with several major airports nearby. Washington, DC (DCA-Ronald Reagan Washington National) is 66.0km from Chester, with luxurious hotels such as Salamander Washington DC and Riggs Washington DC located just 2 to 4.8km away, offering easy access to the airport. Alternatively, Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall) is a mere 40.2km away, featuring top accommodations like Sagamore Pendry Baltimore and Four Seasons Hotel Baltimore, both 12.9km from the airport and providing various transportation services. Lastly, Baltimore, MD (MTN-Martin State) is also 40.2km away, with nearby options like Canopy by Hilton Baltimore Harbor Point.