Hotels in Eastport

Eastport: Where Tranquil Waters Meet Vibrant Culture

Nestled just across the harbor from historic Annapolis, Eastport boasts a vibrant waterfront charm that beckons travelers seeking both relaxation and adventure. This walkable neighborhood is a haven for sailors, with its bustling docks and scenic views of the Chesapeake Bay. Discover eclectic shops, gourmet eateries, and lively art scenes in downtown Eastport, where a blend of maritime heritage and modern flair thrives. Enjoy leisurely strolls along the picturesque waterfront or savor fresh seafood at local favorites. Whether you're exploring its rich history or indulging in a romantic sunset, Eastport is a captivating escape for all.

Discover great hotels in Eastport

Eastport, Annapolis offers a variety of hotel accommodations, from cozy motels to upscale star hotels. You'll find guest rooms with essential amenities and options for budget-friendly stays. With its charming atmosphere, Eastport hotels provide a great base for exploring the area's attractions. Here are some of the best hotels in Eastport that our travelers love:

1. Annapolis Waterfront HotelOpens in a new window: Annapolis Waterfront Hotel is a stylish 4.0-star hotel located in the heart of the city, perfect for leisure travelers seeking an LGBTQIA-friendly atmosphere. With a focus on distinctive experiences, the hotel boasts chic architectural design and modern amenities that ensure a smooth journey. Guests appreciate the convenience of express check-in and curated experiences tailored to city exploration, all in a vibrant urban setting that fosters connection and relaxation.
2. 134 Prince - Luxury Boutique HotelOpens in a new window: 134 Prince - Luxury Boutique Hotel is a charming 2.5-star hotel that offers romantic packages and intimate settings, making it an ideal choice for couples seeking a cozy getaway. Nestled in the city center, this hotel features exceptional food and beverage services, including Champagne Service, to enhance your experience. The ambiance is enhanced by its dedication to providing a memorable romantic atmosphere, ensuring that every detail contributes to a delightful stay.
3. Flag House InnOpens in a new window: Flag House Inn, a welcoming 3.5-star Bed and Breakfast, caters specifically to LGBTQIA travelers looking for a cozy and inclusive vacation experience. This charming property exudes warmth and character, making it a perfect retreat for those seeking relaxation and comfort. With a focus on personal touches and a friendly atmosphere, Flag House Inn is praised for its inviting environment and attention to detail that fosters a memorable stay.

Top locations to stay in Eastport

Staying in Eastport, Annapolis, Maryland, near the U.S. Naval Academy, Chesapeake Bay Bridge, and Sandy Point State Park offers a blend of history, stunning views, and outdoor adventure. The U.S. Naval Academy is rich in heritage, the Chesapeake Bay Bridge boasts breathtaking scenery, and Sandy Point State Park is perfect for relaxation and recreation. For first-time visitors, staying near the U.S. Naval Academy is highly recommended.

1. Near U.S. Naval AcademyOpens in a new window: Staying near the U.S. Naval Academy puts you at the heart of Annapolis's rich maritime history. You can explore iconic sites like the Maryland State House and enjoy cultural attractions such as local theaters. Plus, you're just a stone's throw from the vibrant shopping scene at Westfield Annapolis Mall and Annapolis Harbor Center Shopping Center, perfect for picking up unique souvenirs or enjoying a leisurely shopping day.
2. Near Chesapeake Bay BridgeOpens in a new window: This stunning bridge is not just a landmark; staying nearby offers breathtaking views and easy access to outdoor activities. Explore nearby Sandy Point State ParkOpens in a new window for a relaxing day by the beach. The area also features a variety of cultural attractions, ensuring you can enjoy local performances and art galleries while soaking in the scenic surroundings.
3. Near Sandy Point State Park: Sandy Point State Park is a fantastic place to unwind in nature, with beautiful beaches and picnic areas. Staying near here lets you enjoy a range of outdoor activities like hiking and birdwatching. It's also conveniently close to the Maryland State House and the Chesapeake Bay for some picturesque views and exploration of the local history.

Things to do near Eastport

Eastport invites travelers to explore its stunning beaches and tranquil lakes, ideal for boating or relaxing by the shore. With lush parks for hiking and a vibrant dock area, visitors can enjoy recreational activities and local shopping. Plus, golfing enthusiasts will love the scenic courses, making it a perfect getaway.

• Chesapeake Bay BridgeOpens in a new window – Take a scenic drive across this impressive modern bridge that spans the Chesapeake Bay. The views are breathtaking, offering a perfect opportunity for photos and a unique perspective of the surrounding waters.
• Sandy Point State ParkOpens in a new window – Spend a day exploring this national state park, where you can hike along the trails, enjoy picnicking by the water, or simply relax in the lush natural surroundings. The park provides beautiful views of the bay and is a great spot for outdoor activities.
• Sandy Point BeachOpens in a new window – Head to Sandy Point Beach for a fun day by the water. This beach offers a sandy shoreline perfect for sunbathing, swimming, and beach games. Pack a picnic and enjoy a day of relaxation with family or friends.
• Six Flags AmericaOpens in a new window – Get your adrenaline pumping at Six Flags America, an amusement park filled with thrilling roller coasters and exciting rides. Perfect for families and thrill-seekers alike, you’ll find entertainment options that cater to all ages.
• Breezy Point BeachOpens in a new window – Discover Breezy Point Beach, another beautiful spot for sun and sand. This beach is ideal for swimming, beachcombing, and enjoying a peaceful day by the water, making it a lovely choice for a leisurely afternoon.

4 tips for savvy savings when booking a hotel in Eastport

1. Book for the cheapest times: The most affordable time to visit Eastport is during January, February, and December, when hotel prices tend to be lower. For a budget-friendly trip, a stay of at least 2 to 3 days is recommended to experience the town's key historical and cultural attractions. You can explore notable sites such as the historic lighthouse, military museum, and cultural center, along with recreational spots like the beach known for its stunning sunsets and picnic amenities. Engaging with Eastport's rich history and vibrant culture during this period offers great value for money.
2. Look for last-minute deals on Hotels.com: To discover last-minute hotel deals in Eastport, visit the DealsOpens in a new window or Last-Minute Deals sections on Hotels.com, where you may find discounted rates as your travel date approaches. To maximize your savings, consider enabling email alerts or push notifications for flash sales and exclusive promotions. Additionally, the Smart Shopping tool in the app allows you to compare hotel prices and amenities, increasing your chances of finding cheap deals on Eastport hotels. By staying informed about price drops or room availability, you'll be better positioned to book an affordable last-minute getaway.
3. Be flexible with dates: Prices can fluctuate depending on factors like the hotel's location, star rating, and the time of year, so being flexible with your travel dates might help you save on your stay at an Eastport hotel. For those seeking something special, boutique hotels can provide a more personalized experience and potentially better value. When you book through Hotels.com, we’ll inform you whether the price for your chosen dates is above or below the average. If it turns out to be on the higher side, we’ll suggest alternative dates that could be more affordable, increasing your chances of getting the best deal.
4. Consider your location: Staying near major attractions or downtown areas can be convenient, but it often comes with a higher price tag. For more budget-friendly options, you might want to look at hotels in neighborhoods that are a bit farther out, which usually tend to be cheaper while still offering good access to the sights you want to see. Additionally, consider independent hotels located further from the center, as they can provide a more genuine experience at a more affordable price.

Best time to go to Eastport

Eastport has a varied climate due to its size, so the best time to visit depends on the region and your preferences for weather and crowds. April, June, and July are the peak travel months in Eastport, attracting a higher number of tourists. During this peak period, the weather is mostly sunny, accompanied by light rainfall. On the other hand, February, November, and December tend to be quieter times to visit, marked by light rainfall and mostly sunny conditions.