Hotels in Chester

Chester: Where Island Dreams Meet Marina Adventures

Nestled on the picturesque Eastern Shore of Maryland, Chester offers a charming escape into nature and history. Surrounded by the serene waters of the Chesapeake Bay, visitors can explore its tranquil islands and vibrant marina, perfect for boating and fishing. Just a short drive away lies historic Chestertown, where cobblestone streets and quaint shops invite leisurely strolls. Experience local culture through art galleries and seasonal festivals. Whether you're seeking a romantic getaway or an off-the-beaten-path adventure, Chester's captivating landscapes and rich heritage promise an unforgettable journey. Embrace the beauty and tranquility of this hidden gem! For the 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.

Where to stay in Chester

Some of the best places to stay in Chester are Downtown Baltimore, Historic District and Fells Point. Chester, Maryland is a great base for exploring nearby attractions like Downtown Baltimore, the Historic District, and Fells Point. Downtown Baltimore offers vibrant nightlife and dining, while the Historic District is rich in charm and history. Fells Point features unique waterfront views and boutique shops. For accommodations, you’ll find a range of options from budget motels to luxury hotels, with various room rates and suites available. First-time visitors should consider Downtown Baltimore for its central location and lively atmosphere. Here are some of the best hotels in Chester that our travelers love:

1. Downtown BaltimoreOpens in a new window: Downtown Baltimore is an excellent choice for travelers who enjoy a vibrant city atmosphere combined with business and leisure opportunities. With attractions like the Baltimore Inner Harbor Marina and Oriole Park at Camden Yards, there's plenty to explore. For accommodations, Gramercy Mansion B&BOpens in a new window offers a luxurious experience with business amenities, making it ideal for business travelers. Kimpton Hotel Monaco Baltimore Inner Harbor, an IHG HotelOpens in a new window is also a great option, providing family-friendly facilities and multiple meeting rooms. For a top-tier experience, The Ivy HotelOpens in a new window features upscale services and amenities for both business and family travelers.
2. Historic DistrictOpens in a new window: The Historic District is rich in culture and family-friendly activities, making it a perfect spot for visitors. Highlights include the U.S. Naval Academy and Westfield Annapolis Mall, catering to both history buffs and shoppers. Annapolis Waterfront Hotel, Autograph CollectionOpens in a new window provides a comfortable stay with diverse business amenities and adventure sports options, while The Annapolis InnOpens in a new window is a charming bed and breakfast offering complimentary breakfast. Graduate by Hilton AnnapolisOpens in a new window is another solid choice, allowing pets and featuring business facilities for corporate guests.
3. Fells PointOpens in a new window: Fells Point is known for its lively waterfront and outdoor activities, making it a great destination for adventure seekers. With nearby attractions like the Baltimore Inner Harbor Marina, visitors can enjoy a variety of outdoor experiences. Sagamore Pendry BaltimoreOpens in a new window is a luxurious option that welcomes pets and includes a range of business services. Canopy by Hilton Baltimore Harbor PointOpens in a new window offers a romantic atmosphere with stunning ocean views, perfect for couples, while Lancaster Square by BridgestreetOpens in a new window provides cozy accommodations with entertainment options for a relaxing stay.

What to do in Chester

Three days in Chester offers travelers a chance to explore picturesque islands and serene marinas, perfect for boating and sailing. Enjoy biking along scenic paths, play a round of golf, and unwind with stunning sunsets over tranquil waters, all amidst a backdrop of lush parks and forests. Here's a quick itinerary to make the most of your trip to Chester:

• Day 1: Start your adventure in Chester by crossing the iconic Chesapeake Bay Bridge, where you'll be treated to stunning views of the water. Afterward, head to Sandy Point State Park, an ideal spot for picnicking and enjoying outdoor activities. Spend the afternoon relaxing at Sandy Point Beach, where you can soak up the sun, swim, or take a leisurely walk along the sandy shore. As the day winds down, take in the beautiful sunset on the beach, creating perfect photo opportunities.
• Day 2: Begin your exploration at the Chesapeake Bay Environmental Center, where you can learn about local ecosystems and enjoy scenic trails. Next, head to Matapeake State Park, which offers beach access and hiking trails, perfect for a nature-filled day. Wrap up your day at Island Dog Park, where you can let your furry friends play or simply enjoy the park's peaceful atmosphere. It’s a great way to unwind after a day of exploring.
• Day 3: Kick off with a visit to Eastern Neck National Wildlife Refuge, where you can immerse yourself in nature and spot diverse wildlife. Afterward, venture to the Maryland State House, rich in history and a fantastic place to learn about the state’s heritage. Conclude your day at Love Point State Park, where you can take in the serene views of the Chesapeake Bay, perfect for a reflective end to your trip.

5 tips to find a great Chester hotel deal

1. Book for the cheapest times: If you're looking for an affordable getaway, consider visiting Chester in January, November, or December when hotel rates are at their lowest. For the best experience, plan to stay for at least 2-3 days to fully explore its main attractions, including the beautiful marina and charming islands. This budget-friendly trip offers great value for money while allowing you to enjoy all that Chester has to offer.
2. Look for last-minute deals on Hotels.com: If you're looking for last-minute deals to Chester, you're in luck! Hotels.com offers a great selection of discounted hotel rates. To explore these offers, simply head to the DealsOpens in a new window or Last-Minute DealsOpens in a new window section on Hotels.com, where you could find affordable room rates as your travel date approaches. Additionally, consider enabling email alerts or push notifications from Hotels.com to keep yourself informed about flash sales and special promotions, helping you compare prices and snag cheap hotel deals.
3. Be flexible with dates: Hotel prices may fluctuate depending on factors like the hotel's location, star rating, and the time of year. Therefore, if you're flexible with your travel dates, you might save on hotel expenses in Chester.
4. Consider your location: When booking your stay on Hotels.com for your holiday, take your location into account. Staying closer to major attractions or city centers can be convenient, but it usually tends to be more expensive. For more affordable options, consider hotels in less central areas or neighborhoods, striking a balance between cost and accessibility to the places you plan to visit.
5. Upgrade with One Key: Join Hotels.com's free One Key program and book your next stay in Chester. As a member, you can earn and use rewards points for hotel bookings. Progress through Blue, Silver, Gold and Platinum tiers to unlock various benefits like room upgrades when available, special discounts, and exclusive deals for members. Sign up today.

What to eat in Chester

Here are a few top restaurants to try in Chester, Maryland, United States of America:

• Carmine's N.Y. Pizza Kitchen: Celebrated for its authentic New York-style pizza, Carmine's offers a variety of fresh toppings and house-made sauces that capture the essence of Italian-American cuisine. Their commitment to using quality ingredients ensures each slice is a flavor-packed experience, making it a must-visit for pizza lovers.
• Capriotti's Sandwich Shop: Known for its innovative sandwiches, Capriotti's features unique combinations that highlight local flavors. Their signature subs, especially the Bobbie made with turkey, stuffing, and cranberry sauce, reflect a creative twist on classic American comfort food, providing a delicious taste of tradition in every bite.

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. May to July are the peak travel months in Chester, attracting a higher number of tourists. During this peak period, the weather is mostly sunny, with light rainfall. On the other hand, January, November, and December tend to be quieter times to visit, marked by light rainfall and mostly sunny conditions.