Find hotels in Chester, MD from SAR 342

Top reasons to visit Chester

• Scenic Boardwalk: Enjoy leisurely strolls along Chester's picturesque boardwalk, perfect for taking in views of the water and surrounding nature.
• Outdoor Activities: Explore urban parks and national state parks, offering hiking, biking, and other outdoor adventures for all ages.
• Vibrant Nightlife: Experience Chester's lively nightlife, blending entertainment and relaxation for a memorable evening out.
• Cultural Experiences: Discover the Eastern Shore's rich history and engage with friendly locals to enhance your visit.
• Diverse Accommodations: Choose from a variety of lodging options, including pet-friendly hotels and charming bed & breakfasts.

Find great hotels near Chester

Chester, Maryland, offers a diverse selection of accommodations to suit every traveler’s needs, from pet-friendly hotels to cozy bed & breakfasts. Whether you're visiting for business or planning a family vacation, you'll find top-rated hotels equipped with essential amenities and services. With numerous options available, you can easily discover the best Chester hotels that cater to your preferences and ensure a comfortable stay during your visit.

• Country Inn & Suites by Radisson, Annapolis, MD: This welcoming 3-star hotel offers a delightful stay for travelers seeking a pet-friendly, LGBTQIA-friendly atmosphere. Located 22.5km from Chester, it combines comfort with a focus on inclusivity. Guests appreciate the property's amenities, including a designated dog exercise area and a warm, inviting lobby. Ideal for business travelers or those on leisure trips, this hotel emphasizes quality service and a community feel, making it a great base for exploring the Annapolis area.
• Historic Inns of Annapolis: Situated in a national historic building just 17.7km from Chester, this charming 3.5-star hotel is perfect for families and history enthusiasts. With a city-themed ambiance, it provides a unique glimpse into the past while offering modern conveniences. Families will love the free crib service and child-friendly amenities. The central location ensures easy access to local attractions, making it an excellent choice for those wanting to immerse themselves in Annapolis’s rich history and vibrant culture.
• Graduate by Hilton Annapolis: A sophisticated 4-star accommodation located 17.7km from Chester, Graduate by Hilton Annapolis is ideal for families, business travelers, and pet owners. With a stylish yet comfortable atmosphere, this hotel provides excellent amenities, including free cribs for children and pet-friendly policies, including food and water bowls. Guests enjoy the combination of modern design and thoughtful touches, ensuring a pleasant stay while being conveniently located near local attractions and activities.

Where to stay near Chester

Your vacation in Chester, Maryland promises a delightful blend of outdoor adventures and relaxing experiences. Enjoy sunny days exploring the charming neighborhoods, perfect for family getaways or romantic escapes. Discover the Eastern Shore's rich history and vibrant atmosphere, while connecting with friendly locals. Whether you’re hiking along scenic trails or savoring the local cuisine, Chester offers memorable experiences that will make your trip truly unforgettable.

• Annapolis: Located 17.7km from Chester, Annapolis is a charming city known for its rich maritime heritage. Visitors flock here year-round, with peak travel during the summer months. The city offers a delightful mix of family-friendly activities, outdoor adventures, and cultural experiences. Explore historic sites like the U.S. Naval Academy, enjoy shopping at the local malls, or take a stroll along the waterfront to soak in the scenic views. With its vibrant atmosphere and numerous attractions, Annapolis is a must-visit for anyone looking for a blend of education, leisure, and urban charm.
• Stevensville: Just 1.6km away from Chester, Stevensville is a quaint city perfect for outdoor enthusiasts and families. With peak travel occurring in the spring and summer, visitors can enjoy recreational areas and picturesque boardwalks. The city’s proximity to beautiful beaches and the nearby national state park makes it an ideal destination for romantic getaways or family outings. Don't miss the chance to unwind by the water or indulge in local eateries that offer a taste of the region's culinary delights.
• Grasonville: Situated 6.4km from Chester, Grasonville is a welcoming city that attracts visitors with its stunning outdoor spaces and family-oriented activities. The vibrant boardwalk and recreational areas are perfect for leisurely strolls and family fun. Peak travel times are during the summer months, when tourists flock to the local beaches and esplanades. Grasonville offers a perfect blend of relaxation and adventure, making it an excellent stop for those seeking enjoyable experiences amid natural beauty.

Things to do near Chester

Chester, Maryland, is perfect for outdoor, romantic, and adventurous vacations. Visitors can enjoy the scenic boardwalk, explore educational attractions, and play a round at the local golf course. For the best experiences, immerse yourself in the charming city atmosphere and discover its vibrant nightlife, which promises an exciting blend of entertainment and relaxation. Whether seeking adventure or a cozy evening, Chester offers something for everyone.

Shopping

In Chester, you can shop at Paul Reed Smith Guitars, just 3.2km away. The Queenstown Premium Outlets, 11.3km from Chester, offers a variety of brand-name shops. If you're up for a drive, visit Annapolis Harbour Center, located 22.5km away, featuring diverse shopping and entertainment options.

Recreation

Navy-Marine Corps Memorial Stadium, located 19.3km from Chester, offers an energetic sports atmosphere perfect for fitness enthusiasts. Queenstown Harbor Golf Club, 11.3km away, invites you to enjoy outdoor recreation amidst beautiful landscapes. Ballet Theater of Maryland, also 19.3km away, provides a cultural experience through captivating dance performances.

Adventure

At Annapolis Sailing School, located 16.1km from Chester, you can enjoy thrilling sailing experiences on the beautiful Chesapeake Bay. St Michaels Nature Trail, 20.9km away, offers a serene outdoor adventure amidst lush landscapes. For hiking enthusiasts, the B&A Trail, 27.4km from Chester, showcases stunning scenery and invigorating trails.

Nightlife

Experience a vibrant nightlife in Chester by visiting The Colonial Players for a captivating theater performance, or unleash your adventurous spirit at Annapolis Bowl's arcadeAdventureZone. For a romantic evening, enjoy a show at Avalon Theatre, where entertainment and culture come alive.

Booking tips and Expedia advantages for Chester

To save money on your trip to Chester, Maryland, consider visiting between December and February when hotel prices are lower. Book your stay on a Monday for the best rates, and avoid Saturdays for higher costs. Utilize Expedia's search tool to find budget-friendly hotels and sort options from lowest to highest prices. Additionally, look for package deals that combine your hotel, flights, and activities for extra savings. Take advantage of any beverage discounts, and explore free activities in the area to maximize your budget.

• 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 choices based on your budget, preferred location, and the type of hotel you desire. To find the best prices and deals, simply 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.

Find the best attractions near Chester

Chester, Maryland, is perfect for outdoor and romantic adventures, featuring highlights like urban parks, marinas, and national state parks. Visitors can enjoy a blend of outdoor activities and cultural experiences, making it ideal for families. Nearby attractions and top-notch resorts enhance your stay, ensuring a fulfilling vacation filled with exploration and relaxation.

• U.S. Naval Academy: Explore the rich history and stunning architecture of this prestigious military academy, located 17.7km from Chester. The campus offers guided tours, showcasing its beautiful grounds and impressive buildings, steeped in naval tradition.
• Chesapeake Bay Bridge: Experience breathtaking views from this engineering marvel, situated 11.3km away. The bridge connects the Eastern and Western Shores of Maryland, offering a unique perspective on the region's vibrant city life and stunning waterways.
• Sandy Point State Park: Enjoy outdoor adventures in this picturesque state park, located 11.3km from Chester. With scenic views, hiking trails, and waterfront activities, it’s perfect for nature lovers seeking adventure and relaxation.

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

Traveling to Chester, Maryland, is convenient with three major airports nearby. Washington, DC (DCA-Ronald Reagan Washington National) is 66.0km away, with upscale options like the Salamander Washington DC and Riggs Washington DC, both offering easy airport access. Baltimore, MD (BWI-Baltimore Washington Intl. Thurgood Marshall) is closer at 40.2km, featuring luxurious hotels like the Sagamore Pendry Baltimore, which provides a 24-hour shuttle service. Lastly, Easton, MD (ESN-Easton - Newnam) is just 27.4km away, where you can stay at the Inn at Perry Cabin. Each airport offers various transportation services to ensure a smooth journey to Chester.