Find hotels in Chester, MD from $97

Top reasons to visit Chester

• Scenic Waterfront Strolls: Enjoy relaxing walks along Chester's picturesque waterfront, perfect for soaking in the sun and beautiful views.
• Outdoor Recreation: Explore urban parks and a marina, offering various activities for outdoor enthusiasts and families alike.
• Vibrant Downtown Area: Discover charming shops and local dining options in Chester's lively downtown, ideal for a fun day out.
• Historic Atmosphere: Experience the rich history of Chester through its historic houses and nearby cultural sites.
• Diverse Lodging Options: Choose from pet-friendly hotels, cozy bed & breakfasts, and family-friendly accommodations for a comfortable stay.

Find great hotels near Chester

Experience the charm of Chester, Maryland, with a variety of lodging options tailored to every traveler. Whether you're seeking a pet-friendly hotel, a cozy bed & breakfast, or accommodations for a family vacation, Chester has you covered. Enjoy convenient access to essential amenities designed for business travelers and leisure seekers alike. Discover the best hotels in Chester that promise comfort and hospitality for a memorable stay.

• Country Inn & Suites by Radisson, Annapolis, MD: Experience a warm and welcoming atmosphere at this 3-star hotel, rated 9.0 by guests. Located 14 miles from Chester, this property is ideal for travelers seeking a pet-friendly environment with business travel amenities. Enjoy spacious rooms equipped for relaxation and productivity. The hotel offers convenient features such as a dog exercise area and flexible pet policies, ensuring a comfortable stay for you and your furry companions.
• Graduate by Hilton Annapolis: With a guest rating of 9.4, this 4-star hotel offers a charming blend of family-friendly and business-oriented accommodations just 11 miles from Chester. The Graduate by Hilton embraces a collegiate theme, making it perfect for families and professionals alike. Enjoy amenities tailored for children, including free cribs, and take advantage of the welcoming pet policy. Guests appreciate the vibrant atmosphere and modern comforts this property provides, making it a great choice for all.
• Historic Inns of Annapolis: Nestled in a national historic building, this 3.5-star hotel boasts a guest rating of 9.0 and is located 11 miles from Chester. Ideal for those seeking a unique adventure and family vacation, the Historic Inns of Annapolis offers exciting recreational activities nearby, such as kayaking and hiking. The hotel also caters to families with children-friendly amenities, ensuring a delightful stay for guests of all ages. Immerse yourself in the rich history and charm of this remarkable property.

Where to stay near Chester

Chester, Maryland, is a charming city perfect for outdoor enthusiasts and beach lovers. With its sunny weather and scenic views, visitors can enjoy relaxing strolls along the waterfront or explore the vibrant downtown area. Nearby, experience family-friendly neighborhoods with welcoming locals and a rich historical atmosphere. Whether you’re seeking adventure or a serene getaway, Chester promises a delightful vacation filled with charm and memorable moments.

• Stevensville: Nestled just a mile from Chester, Stevensville offers a charming blend of outdoor adventure and scenic beauty. With its peak visitor numbers in April and the summer months of June and July, this city is a popular destination for those seeking a beach experience. Enjoy the local recreational areas and picturesque boardwalks, perfect for leisurely strolls or picnics. The nearby Chesapeake Bay and state parks provide ample opportunities for exploration and relaxation, making Stevensville an ideal spot for nature lovers and families alike.
• Annapolis: A mere 11 miles from Chester, Annapolis is a vibrant city known for its rich history and family-friendly atmosphere. With visitor numbers peaking in the summer months of July and August, this charming city offers a diverse range of experiences. Explore the historic academy, enjoy shopping at local centers, or take in the breathtaking views of the bay and beach. Whether you're interested in educational opportunities or simply soaking in the city's unique culture, Annapolis promises an engaging visit year-round.
• Kent Narrows: Located just 3 miles from Chester, Kent Narrows is a quaint village that attracts visitors with its picturesque waterfront and family-oriented activities. The village experiences peak tourist arrivals during the summer months of June to August, making it a lively destination for beachgoers. With its inviting boardwalk and various shopping centers, Kent Narrows offers a delightful blend of leisure and recreation. The nearby esplanade and stunning views of the bay make it a perfect getaway for those looking to unwind and enjoy the natural surroundings.

Things to do near Chester

Chester, Maryland, offers a delightful escape for outdoor enthusiasts and beach lovers. Enjoy scenic strolls along the boardwalk, explore recreational areas, and take advantage of local attractions. Whether you're looking for a vibrant shopping experience or guided tours to discover the area's charm, Chester has something for everyone. Embrace the picturesque views and unique amenities that make this quaint town a perfect getaway.

Shopping

For unique gifts and souvenirs, explore local shops in Chester, like The Gifted Bird and Chester River Wine & Cheese. If you're up for a drive, head to the nearby Queenstown Premium Outlets for a wider selection of brands and deals, just a short distance away.

Recreation

Experience luxury at Old South Country Club, where you can enjoy golf amidst beautiful scenery. Indulge in the serene atmosphere, relax in the clubhouse, and savor fine dining options, all while embracing the peaceful surroundings that enhance your wellness journey.

Adventure

Explore the scenic Chester River by renting a kayak or paddleboard, enjoying the beautiful waterways and wildlife. For a thrilling experience, head to the nearby Chesapeake Bay for fishing or crabbing, soaking in the sun while engaging in these fun outdoor activities.

Nightlife

Explore the lively atmosphere at The Narrows Restaurant for waterfront dining and cocktails. For a more casual vibe, check out The Fisherman's Inn, where you can enjoy local seafood and live music. Don't miss the nearby craft breweries for a taste of local brews and a fun night out.

Booking tips and Expedia advantages for 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: Utilize Expedia’s search tool to tailor your options based on your budget, desired location, and preferred type of accommodation. For instance, selecting the Eco-certified filter will show you 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 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 enthusiasts and beach lovers, featuring beautiful scenery and a variety of attractions. Visitors can explore urban parks, a marina, and historic houses, making it an ideal destination for culture-seekers and families alike. With plenty of options for outdoor activities and enriching experiences, Chester promises a memorable vacation for all who visit.

• Chesapeake Bay Bridge: Experience the impressive engineering of this modern marvel, spanning over 4 miles. With stunning views of the Chesapeake Bay and the surrounding landscapes, this iconic bridge offers a unique perspective of the area and the bustling city vibes nearby.
• Sandy Point State Park: Immerse yourself in the natural beauty of this national state park, featuring scenic trails and abundant wildlife. Perfect for adventure seekers, you can hike, bike, or picnic while enjoying the great outdoors and refreshing vibes.
• Sandy Point Beach: Relax and soak up the sun at this beautiful beach, known for its soft sands and inviting waters. It's an ideal spot for swimming, beach games, and enjoying the laid-back coastal atmosphere.

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, you have a few airport options. Philadelphia International Airport (PHL) is 84 miles away, with nearby hotels like W Philadelphia and The Rittenhouse, both 6 miles from the airport. Washington, D.C.'s Ronald Reagan Washington National Airport (DCA) is closer at 41 miles, offering luxury stays such as the InterContinental Washington D.C. - The Wharf and Salamander Washington DC, both 2 miles away. Washington Dulles International Airport (IAD) is also accessible at 62 miles, with hotels like The Westin Washington Dulles Airport and Washington Dulles Airport Marriott, just 1 mile and 0.4 miles away, respectively. Each hotel provides convenient transportation to its corresponding airport.