Find hotels in Chester, MD from $76

Top reasons to visit Chester

• Outdoor Adventures: Chester offers a variety of outdoor activities, including golfing, marinas, and urban parks, perfect for family fun.
• Beautiful Beaches: Enjoy sandy shores and scenic views, ideal for relaxation and beach vacations.
• Local Nightlife: Experience the community's essence at local bars and restaurants, showcasing unique flavors and atmosphere.
• Charming Accommodations: Find a range of lodging options, from pet-friendly hotels to cozy bed and breakfasts.
• Nearby Attractions: Explore surrounding cities and neighborhoods rich in history and culture for a complete getaway experience.

Find great hotels near Chester

Explore the delightful hotel accommodations in Chester, Maryland, perfect for your getaway. Whether you're looking for pet-friendly options, family-friendly environments, or business-themed stays, Chester offers a variety of hotels and charming bed and breakfasts. With numerous hotel reviews available, you can easily find the best lodging that suits your needs for a memorable vacation experience.

• Historic Inns of Annapolis: Experience a blend of rich history and modern comfort at the Historic Inns of Annapolis. Located 11 miles from Chester, this charming 3.5-star hotel is perfect for business travelers and families alike. The property features well-equipped meeting rooms and versatile conference spaces, catering to your professional needs. Families will appreciate the child-friendly amenities, including free cribs and a welcoming atmosphere. With its quaint architecture and central location, it also serves as an excellent base for exploring Annapolis's cultural heritage.
• Country Inn & Suites by Radisson, Annapolis, MD: This 3-star hotel, situated 14 miles from Chester, offers a warm and inviting environment ideal for both business and leisure travelers. The Country Inn & Suites by Radisson is pet-friendly and LGBTQIA welcoming, ensuring a comfortable stay for all guests. Enjoy convenient business amenities, including a 24-hour accessible business center and multiple meeting rooms. The hotel also features a dedicated dog exercise area, making it perfect for pet owners. Relax in cozy accommodations designed for a homely feel, and take advantage of its close proximity to Annapolis attractions.
• Graduate by Hilton Annapolis: Located 11 miles from Chester, the Graduate by Hilton Annapolis is a stylish 4-star hotel that caters to business travelers and pet owners while embracing LGBTQIA inclusivity. The hotel’s vibrant atmosphere and unique decor reflect the local culture, providing an engaging experience. Business amenities such as meeting rooms and conference spaces are readily available for your professional needs. Guests traveling with pets will find comfort in knowing that they are welcome, with provisions for food and water bowls. This hotel promises a memorable stay with its blend of comfort, convenience, and character.

Where to stay near Chester

Discover the charm of Chester, Maryland, where outdoor adventures and family-friendly activities await. This picturesque destination on the Eastern Shore offers sunny weather and a welcoming atmosphere, perfect for a memorable getaway. Explore nearby cities and neighborhoods that showcase rich history, relaxation, and friendly faces. Whether you're seeking a beach vacation or a tranquil retreat, Chester has something for everyone to enjoy on their family getaway.

• Annapolis: Located 11 miles from Chester, Annapolis is a charming city known for its rich maritime history and vibrant atmosphere. This city attracts visitors year-round, with peak travel times from May to July. Annapolis offers a delightful blend of family-friendly activities, outdoor adventures, and city experiences. Visitors can explore its historic academy, relax by the beach or lake, and indulge in shopping at its local mall centers. The picturesque waterfront and historic streets make it an ideal destination for both relaxation and exploration.
• Stevensville: Just 1 mile from Chester, Stevensville is a quaint city that offers a perfect getaway for families and outdoor enthusiasts. The travel experience here is moderately seasonal, with peak visits in April and from June to July. Stevensville is renowned for its beautiful scenery and recreational areas, including a scenic boardwalk that invites leisurely strolls. Nearby landmarks like the beach and national state park provide ample opportunities for outdoor activities, making it a fantastic spot for those looking to connect with nature while enjoying local shopping centers.
• Kent Narrows: A charming village located 3 miles from Chester, Kent Narrows offers a romantic and family-friendly atmosphere. With travel peak times from June to August, this destination is perfect for summer outings. Visitors can explore the vibrant boardwalk, enjoy shopping at local centers, and discover stunning natural features like the nearby beach and national state park. The esplanade offers scenic views and opportunities for relaxation, making Kent Narrows a delightful choice for those seeking both adventure and tranquility.

Things to do near Chester

Chester, Maryland is perfect for outdoor family and beach vacations, offering a range of activities like golfing and exploring recreational areas. Visitors can enjoy scenic golf courses and experience the area's natural beauty. For nightlife, check out local bars and restaurants that capture the essence of the community. Overall, Chester provides a blend of relaxation and adventure, making it an ideal destination for a memorable getaway.

Shopping

In Chester, visit Paul Reed Smith Guitars, just 2 miles away for unique gifts. Queenstown Premium Outlets, 7 miles away, offers a variety of shops and family-friendly entertainment. If you're up for a drive, check out Annapolis Harbour Center, located 14 miles away, for more shopping and dining options.

Recreation

Experience the energetic atmosphere at Navy-Marine Corps Memorial Stadium, just 12 miles away, where you can enjoy various sporting events. For a tranquil day, head to Queenstown Harbor Golf Club, 7 miles away, and immerse yourself in nature while playing a round of golf amidst beautiful landscapes.

Adventure

Experience the thrill of sailing at Annapolis Sailing School, located 10 miles from Chester, where outdoor sports meet adventure on the water. For family fun, visit Chesapeake Beach Water Park, 24 miles away, offering exciting rides and entertainment. Enjoy scenic views while hiking on the B&A Trail, 17 miles from Chester.

Nightlife

Experience the vibrant nightlife in Chester by visiting The Colonial Players for a captivating theater performance, or unleash your competitive spirit at Annapolis Bowl's arcadeAdventureZone. For more entertainment, check out Avalon Theatre for a delightful family-friendly show.

Booking tips and Expedia advantages for Chester

To save money on your trip to Chester, plan your visit between December and February for lower accommodation rates. Consider booking your stay on a Monday, the least expensive day, and avoid Saturdays when prices peak. Use Expedia to compare prices and consider package deals that combine flights, hotels, and activities for additional savings. Join the One Key membership for exclusive discounts and earn OneKeyCash for future bookings. Look for free activities and explore the town on foot to cut transportation costs and enhance your experience.

• 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: Utilize Expedia’s search tool to refine your options based on your budget, desired location, and preferred hotel type. To find the best prices and deals, make sure to sort the price filter from lowest to highest.
• Consider bundling your trip: You can save money by combining your hotel stay in Chester with your flights and activities through an Expedia package deal.
• Become a One Key member: Join Expedia's One Key membership program for exclusive discounts and deals on hotel bookings. You can also earn OneKeyCash to use on future selected hotels.

Find the best attractions near Chester

Chester, Maryland, is perfect for outdoor and family beach vacations, offering a variety of attractions such as urban parks, marinas, and sandy shores. Visitors can enjoy a blend of outdoor activities and cultural experiences while exploring the area. For an unforgettable stay, consider checking out the best resorts and nearby attractions that showcase the charm of Chester and its surroundings.

• U.S. Naval Academy: A historic institution located 11 miles from Chester, the U.S. Naval Academy offers a glimpse into military tradition and training. Visitors can explore its stunning architecture and scenic grounds, steeped in naval history.
• Chesapeake Bay Bridge: This iconic modern bridge, situated 7 miles away, connects the Eastern and Western shores of Maryland. It's not only a vital transportation link but also a beautiful architectural landmark that provides breathtaking views of the bay.
• Sandy Point State Park: Located 7 miles from Chester, this national park is perfect for outdoor enthusiasts. With its adventure activities, scenic landscapes, and opportunities for recreation along the shoreline, it's a fantastic destination for nature lovers.

Best time to go to Chester

The best time to visit Chester is dependent 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	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

Traveling to Chester, Maryland, is convenient with several major airports nearby. Washington, DC (DCA-Ronald Reagan Washington National) is about 41 miles away, with excellent hotels such as the 5-star InterContinental Washington D.C. - The Wharf and Riggs Washington DC, both within 3 miles of the airport. Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall) is closer at 25 miles, featuring the luxurious Sagamore Pendry Baltimore and Four Seasons Hotel Baltimore, both offering airport shuttle services. Lastly, Easton, MD (ESN-Easton - Newnam) is just 17 miles away, with the 5-star Inn at Perry Cabin and Inn at 202 Dover nearby, making it easy to find comfortable accommodations.