Hotels in Chester

Chester: Where Tranquil Islands Embrace the Thrill of the Marina

Nestled along the serene shores of the Chesapeake Bay, Chester, Maryland, is a charming retreat for nature lovers and boating enthusiasts. This idyllic destination boasts picturesque marinas and access to beautiful islands, making it perfect for kayaking, fishing, and leisurely strolls along the waterfront. Explore the lush landscapes of nearby parks or indulge in fresh seafood at local eateries. With its tranquil atmosphere and stunning sunsets, Chester offers a romantic escape and an off-the-beaten-path experience that invites you to unwind and connect with nature. Discover the hidden gems of this captivating bay town.

Discover great hotels in Chester

Chester, Maryland offers a variety of hotel accommodations, ranging from cozy inns to upscale options. You can find comfortable stays with convenient access to local attractions, ensuring a relaxing experience whether you're on a family vacation or a weekend getaway. Enjoy a blend of charm and modern amenities during your stay. Here are some of the most popular hotels with our travelers in Chester:

1. Kent Island ResortOpens in a new window: Kent Island Resort is a charming 3.5-star hotel perfect for leisure travelers looking to indulge in a golf-themed vacation experience. This property features an array of golf-related activities, allowing guests to fully immerse themselves in their passion for the sport. With its well-designed facilities, this hotel consistently receives praise for its comfortable accommodations and engaging atmosphere, making it a favorite among golf enthusiasts seeking a memorable getaway.
2. The Inn at Chesapeake Bay Beach ClubOpens in a new window: The Inn at Chesapeake Bay Beach Club is an upscale 4.0-star hotel that caters to business travelers seeking a luxurious experience with spa amenities. The hotel boasts a full-service spa, offering a variety of treatments such as facial treatments, sports massages, and sauna sessions for ultimate relaxation. With sophisticated meeting spaces and 24-hour business services, it provides a seamless blend of work and leisure. This hotel is frequently noted for its elegant ambiance and exceptional service, making it an ideal choice for professionals who value comfort and indulgence during their trips.
3. Hyatt Place Kent Narrows & MarinaOpens in a new window: Hyatt Place Kent Narrows & Marina is a welcoming 3.0-star hotel, ideal for travelers who desire a pet-friendly environment while maintaining a business-oriented focus. This hotel offers accessible business facilities and meeting rooms, ensuring that guests can efficiently conduct their affairs. The property stands out for its accommodating pet policies, allowing travelers to enjoy their stay alongside their furry companions. Frequent visitors appreciate the inviting atmosphere and convenient amenities, making it a popular choice for those balancing work and leisure with their beloved pets.

Top locations to stay in Chester

Some great areas to stay in when visiting Chester, Maryland, are Annapolis, Grasonville, and Stevensville. Annapolis offers a vibrant university atmosphere, Grasonville boasts beautiful marinas, and Stevensville is known for its delightful dining options. For first-time visitors, Annapolis is the best choice, providing a mix of history, culture, and waterfront charm.

1. AnnapolisOpens in a new window: Annapolis is a vibrant, historic city known for its charming waterfront and rich maritime heritage. Staying here means you can explore the picturesque streets lined with colonial architecture and enjoy the local arts scene. The city is famous for its sailing culture, making it a great spot for water activities. Plus, with a variety of shops and boutiques, you’ll find unique souvenirs and gifts. Don’t miss the lively farmers' market and cultural attractions that showcase the area’s history and creativity.
2. GrasonvilleOpens in a new window: Grasonville offers a laid-back atmosphere with beautiful marina views, perfect for those looking to relax by the water. This quaint area is ideal for boating and fishing enthusiasts, with plenty of opportunities for outdoor activities. Explore local parks and nature trails for a bit of adventure, or simply unwind at one of the scenic waterfront spots. Grasonville is a peaceful retreat while still being close to the attractions of the surrounding areas.
3. StevensvilleOpens in a new window: Stevensville is a delightful town that focuses on dining and local charm. It features a range of eateries that showcase fresh, local cuisine, making it a foodie’s paradise. The town’s friendly community vibe and rich history invite you to explore its quaint shops and spend time outdoors. With beautiful parks and scenic views, it’s a great spot for leisurely strolls or family picnics. Stevensville’s relaxed pace makes it an excellent choice for those looking to unwind and enjoy the simple pleasures of life.

Things to do in Chester

Chester invites travelers to explore its stunning natural landscapes, from serene lakes and lush forests to picturesque coastlines. Enjoy thrilling activities like sailing, biking along scenic trails, or playing a round of golf. Don't miss enchanting sunsets that paint the sky in vibrant hues—it's a perfect escape for outdoor enthusiasts!

• Rock Hall HarborOpens in a new window – Drop by Rock Hall Harbor to soak in the maritime charm of this picturesque harbor. Enjoy watching boats glide in and out while you relax on the shore or grab a bite at a nearby eatery. The surrounding scenery offers perfect photo opportunities and a chance to appreciate the beauty of the Chesapeake Bay.
• Chesapeake Bay BridgeOpens in a new window – Take a drive across the iconic Chesapeake Bay Bridge, a modern engineering marvel that spans the bay. The breathtaking views from the bridge provide an unforgettable experience, especially as the sun sets or rises, painting the sky with vibrant colors.
• Sandy Point State ParkOpens in a new window – Explore Sandy Point State Park, a sprawling national park where you can hike scenic trails, picnic with family, or simply enjoy the lush greenery. The park's diverse habitats attract a variety of wildlife, making it a haven for nature lovers.
• Sandy Point BeachOpens in a new window – Head to Sandy Point Beach for a day of sun and fun. Lay out your towel on the sandy shores, splash in the refreshing waters, or take a leisurely stroll along the beach. It’s an ideal spot for families looking to relax and make lasting memories.
• Maryland Quiet Waters ParkOpens in a new window – Unwind at Maryland Quiet Waters Park, an urban oasis featuring serene walking paths and tranquil ponds. This park is perfect for a peaceful afternoon stroll, birdwatching, or simply escaping the hustle and bustle of everyday life amidst beautiful nature.

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 may drop. For a great value for money experience, plan to stay at least 2 to 3 days. This duration is perfect for discovering Chester's rich history and culture, including its iconic landmarks and scenic spots. You can enjoy activities like biking by the marina, exploring the islands, or taking part in sailing adventures. With affordable options available, visitors can also indulge in delicious seafood while soaking in stunning sunsets and engaging in birdwatching.
2. Look for last-minute deals on Hotels.com: To uncover last-minute deals to Chester, visit the DealsOpens in a new window or Last-Minute DealsOpens in a new window section on Hotels.com, where you may discover discounted rates on hotels as your travel date approaches. Consider enabling email alerts or push notifications to stay informed about flash sales and unique promotions, so you don’t miss any chances to save. Additionally, the Smart ShoppingOpens in a new window tool available in the app allows you to compare hotel prices and amenities, helping you identify the best options. With these resources, you’re more likely to see great deals and book a spontaneous getaway.
3. Be flexible with dates: Prices can fluctuate based on factors like the hotel's location, star rating, and the time of year, so being flexible with your travel dates may help you save on your stay at a hotel in Chester. If you're looking for a unique experience, boutique hotels often provide a more personalized touch and could offer better value. When you book through Hotels.com, we’ll inform you if the price for your chosen dates is above or below the average. If the price is on the higher end, we’ll suggest more affordable dates to increase your chances of getting the best deal.
4. Consider your location: Staying near key attractions or city centers can be convenient, but it usually tends to come with higher costs. For more budget-friendly options, consider hotels in less central neighborhoods, allowing you to balance price with accessibility to the places you want to visit. You might also look into independent hotels a bit further out, as they can offer a more authentic and often more affordable experience.
5. Become a Member: Joining as a free member is a great way to enhance your travel experience in Chester and beyond! Here are some key benefits you can enjoy: - Exclusive Member Prices: Access special rates on over 100,000 hotels worldwide, helping you save on your next stay. - Tier Progression: Quickly move up through membership tiers and unlock additional perks. - Free Room Upgrades: Enjoy complimentary upgrades when available, making your stay even more comfortable. - Food and Beverage Discounts: Take advantage of discounts at select VIP Access properties, allowing you to indulge while saving. Don’t miss out on these fantastic benefits. Sign up today and start planning your next getaway in Chester!

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 is usually the wettest month. June to August are the peak travel months in Chester, attracting a higher number of tourists. During this peak period, the weather is mostly sunny, accompanied by light rainfall. On the other hand, January, February, and December tend to be quieter times to visit, marked by light rainfall and mostly sunny conditions.