Hotels in Chester

Discover Chester: Where Island Dreams Meet Marina Magic

Nestled along the picturesque shores of the Chesapeake Bay, Chester, Maryland, is a hidden gem for nature lovers and water enthusiasts. With its inviting marinas and charming islands, this tranquil destination offers idyllic settings for boating, fishing, and kayaking. Explore the lush landscapes and wildlife-rich parks, or relish a leisurely stroll along the waterfront. Chester's close-knit community exudes warmth, making it perfect for romantic getaways or family adventures. Whether you're savoring fresh seafood at local eateries or soaking in stunning sunsets, Chester promises a serene escape brimming with natural beauty and captivating experiences. For our best hotel rates in Chester and to enhance your stay, be sure to check out Hotels.com's Last-Minute DealsOpens in a new window on travel.

Discover great hotels in Chester

Chester, Maryland offers a range of hotel accommodations from cozy inns to comfortable mid-range hotels. Visitors can expect friendly service and convenient amenities, making it easy to relax after exploring the scenic surroundings. Whether you prefer a quaint bed and breakfast or a more modern hotel, Chester has options to suit various preferences. These are some of the hotels preferred by our travelers in Chester:

1. Annapolis Waterfront HotelOpens in a new window: This elegant 4.0-star hotel offers a blend of business and natural experiences in the heart of Chester. The property features a rooftop terrace, providing a serene outdoor space for relaxation. Guests appreciate the clean and comfortable rooms, and the convenient location for exploring nearby Annapolis. A focus on wellness and natural surroundings enhances the stay, making it an ideal choice for leisure travelers seeking comfort and quality amenities.
2. Inn at Perry CabinOpens in a new window: A luxurious 5.0-star resort, Inn at Perry Cabin is perfect for travelers seeking an upscale family getaway or a memorable anniversary. The property boasts exquisite service, beautifully designed accommodations, and stunning surroundings. With a focus on relaxation, guests can enjoy the high-end amenities, including a variety of dining options and the opportunity to engage in golf activities. The positive sentiments highlight the enchanting atmosphere and superb service, ensuring a delightful stay.
3. The Inn at Chesapeake Bay Beach ClubOpens in a new window: This stylish 4.0-star hotel caters to spa enthusiasts looking for a rejuvenating retreat. Featuring an onsite spa with a range of treatments and a seasonal outdoor pool, it promises an indulgent experience. The well-appointed rooms and inviting ambiance provide a tranquil escape. Guests rave about the exceptional dining options and the overall quality of their stay, making it a sought-after destination for those seeking relaxation and pampering in a sophisticated environment.

Top locations to stay in Chester

When visiting Chester, Maryland, great areas to stay include Eastport, Murray Hill, and the Historic District. Eastport offers vibrant nightlife and outdoor adventures near the Chesapeake Bay. Murray Hill features charming residential atmosphere and local dining options. The Historic District boasts rich history and proximity to attractions. For first-time visitors, Eastport is the best choice, blending activity and scenic beauty.

1. EastportOpens in a new window: Eastport is a charming waterfront neighborhood that offers a unique blend of maritime culture and vibrant local life. Staying here means you're just a stone's throw away from the scenic Chesapeake Bay, where you can enjoy stunning views and perhaps even some sailing adventures. The area features delightful shops and eateries that showcase local flavors, making it a great spot for foodies. Plus, you're conveniently close to popular attractions like Sandy Point State Park, perfect for a leisurely day outdoors.
2. Murray HillOpens in a new window: Murray Hill is a picturesque area known for its historic homes and quiet streets, making it a peaceful retreat while still being near the action. This neighborhood boasts lovely parks and scenic walking paths that provide a serene escape. You'll also be within easy reach of the Chesapeake Bay Bridge, offering spectacular views and access to nearby attractions. It's a delightful place to unwind after a day of exploring without being too far from the vibrant offerings of Annapolis.
3. Historic DistrictOpens in a new window: The Historic District is where history comes alive with its well-preserved buildings and rich heritage. Staying here means you can stroll through streets lined with charming shops, galleries, and cultural attractions that reflect the area's storied past. It's a perfect base for exploring local landmarks and enjoying community events. Plus, you're not far from Sandy Point State Park for some outdoor fun, making it an excellent choice for travelers looking to immerse themselves in the local culture while being close to nature.

Things to do in Chester

Chester enchants visitors with its scenic waterfront, where islands and marinas invite fun-filled days of boating and sailing. Explore lush parks and serene forests perfect for biking or golfing, and unwind with breathtaking sunsets that paint the sky. It's a delightful retreat for nature lovers and outdoor enthusiasts alike!

• Chesapeake Bay BridgeOpens in a new window – Drive across this architectural marvel, where you'll be surrounded by stunning views of the Chesapeake Bay. Don't forget to stop at designated viewpoints to snap photos of the bridge's impressive span and the sparkling waters below.
• Sandy Point State ParkOpens in a new window – Spend a day exploring the vast landscapes of this national park, where you can hike scenic trails, enjoy picnicking areas, and take in the natural beauty of the shoreline along the bay. Look out for local wildlife as you wander through the diverse habitats.
• Sandy Point BeachOpens in a new window – Relax on the sandy shores of Sandy Point Beach, perfect for sunbathing or building sandcastles. The gentle waves are great for a refreshing swim, and you can enjoy a beachside stroll with picturesque views of the Chesapeake Bay.
• Chesapeake Bay Environmental CenterOpens in a new window – Engage with nature at this environmental center, where you can learn about the local ecosystem through interactive exhibits. Take a guided tour or explore the walking trails that wind through marshes and forests, providing chances to spot various bird species.
• Matapeake State ParkOpens in a new window – Discover the beauty of Matapeake State Park, where you can hike along trails that offer panoramic views of the bay. Join in on recreational activities like fishing or simply unwind while soaking in the serene surroundings.

5 tips for savvy savings when booking a hotel in Chester

1. Book for the cheapest times: The most budget-friendly time to visit Chester is during January, February, and December when hotel prices are typically lower. For those looking to explore the city’s remarkable landmarks, rich history, and cultural offerings, a stay of at least 2 to 3 days is recommended. This allows visitors to enjoy attractions such as the beautiful islands and the scenic marina, all while making the most of their travel budget. With prices potentially dropping during these months, it's a great opportunity for travelers seeking affordable experiences.
2. Look for last-minute deals on Hotels.com: To book hotels in Chester, you may discover great options by checking the DealsOpens in a new window or Last-Minute DealsOpens in a new window sections on Hotels.com, where discounted rates are often available as your travel date approaches. Consider enabling email alerts or push notifications to stay informed about flash sales and special promotions, increasing your chances of finding cheap hotel deals. Additionally, the Smart ShoppingOpens in a new window feature in the app allows you to compare room rates and amenities, so if prices drop or rooms become available, you could be among the first to know and secure your last-minute getaway.
3. Be flexible with dates: Prices can fluctuate based on various factors, including the hotel's location, star rating, and the time of year. Being flexible with your travel dates may help you save on your stay in a Chester hotel. If you're seeking unique accommodations, boutique hotels often provide a more personalized experience and can sometimes offer better value. When you book through Hotels.com, we'll inform you if the price for your chosen dates is higher or lower than the average. If the price is on the higher end, we’ll recommend alternative dates that could help you secure a better deal.
4. Consider your location: Staying near major attractions or city centers can be convenient but usually tends to come with a higher price tag. For more budget-friendly options, consider hotels in less central neighborhoods, which can help you strike a balance between cost and accessibility to the sites you want to visit. You might also look into independent hotels located a bit further out, as they often provide a more authentic and affordable experience.
5. Join One Key™: Become a One Key MemberOpens in a new window for free and book your next stay in Chester. Save on over 100,000 hotels worldwide with exclusive member prices. As a member, you can quickly progress through the tiers and enjoy perks, like free room upgrades when available and food and beverage discounts at select VIP Access properties.

Best time to go to Chester

Chester experiences its lowest average temperature in January, at 35.1°F (1.7°C), while July is the hottest month, with an average temperature of 77.9°F (25.5°C). July tends to be the wettest month.