Hotels in Chesapeake Bay

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Top landmarks in Chesapeake Bay

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Cruise the bay's tranquil waters, spotting ospreys and exploring charming waterfront towns like St. Michaels. Feast on succulent blue crabs and fresh oysters at local seafood shacks dotting the shoreline.

USS Wisconsin BB-64 featuring a marina

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There are lots of reasons to book your Chesapeake Bay trip with us: our free cancellations on selected hotels gives you flexibility, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.

Find out more about Chesapeake Bay

Find out more about Chesapeake Bay

Chesapeake Bay: Where Nature Dances with History

Discover the enchanting Chesapeake Bay, a serene waterfront getaway that beckons with its stunning coastal views and rich maritime heritage. Stretching across Maryland and Virginia, this picturesque destination offers charming towns like Chesapeake Beach, where you can unwind on sandy shores or indulge in fresh seafood at local eateries. Explore the lush landscapes, embark on boat tours to spot playful dolphins, or delve into history at the nearby monuments. Whether you seek adventure or relaxation, Chesapeake Bay’s tranquil charm and breathtaking sunsets make it a perfect romantic escape or off-the-beaten-path adventure.

Discover great hotels near Chesapeake Bay

Chesapeake Bay offers a variety of hotel accommodations, from oceanfront resorts to cozy inns. Many feature spacious guest rooms and waterfront views, perfect for relaxing after a day of exploring. Whether you seek a romantic getaway or a family-friendly retreat, you'll find options that suit your style. Here are some of the most popular hotels with our travelers near Chesapeake Bay:

  1. Budget Inn By OYO Nassawadox Hwy 13Opens in a new window: This inviting 2.0-star hotel is perfect for leisure travelers seeking a beach getaway. With direct access to the sandy shores, it offers a delightful beach experience that emphasizes relaxation and tranquility. The property features a friendly atmosphere and amenities that cater to a pet-friendly vacation, making it a great choice for those who wish to bring their furry companions along. Guests appreciate the welcoming vibe and the opportunity to unwind by the beach, creating memorable moments in a picturesque setting.
  2. Holiday Inn Express and Suites ExmoreOpens in a new window: Holiday Inn Express and Suites Exmore is a stylish 2.5-star hotel designed with business travelers in mind. It boasts a range of amenities tailored for professional needs, including multiple meeting rooms and an accessible business center. This property stands out for its welcoming atmosphere, making it an ideal choice for those seeking a productive yet comfortable stay. Visitors often commend the seamless experience, exceptional service, and the ability to balance work and relaxation effectively in a well-equipped environment.
  3. Hampton Inn & Suites Exmore - Eastern ShoreOpens in a new window: Perfect for leisure travelers, Hampton Inn & Suites Exmore - Eastern Shore is a chic 2.5-star hotel that combines modern comfort with a pet-friendly policy. This property is thoughtfully designed to create an inviting atmosphere for LGBTQIA travelers, featuring stylish accommodations and welcoming amenities. Guests revel in the unique experiences offered at this hotel, which fosters a sense of community and acceptance. The overall sentiment highlights the delightful ambiance and the opportunity to enjoy a memorable vacation while feeling right at home.

Things to do near Chesapeake Bay

Chesapeake Bay offers a stunning blend of sandy beaches, lush forests, and serene waterways, perfect for outdoor enthusiasts. Enjoy thrilling water sports, invigorating hikes, and tranquil birdwatching. With vibrant festivals and live music to savor, this picturesque waterfront destination invites you to explore its natural beauty and lively atmosphere.

  • Deltaville MarinaOpens in a new window – Dock your boat or enjoy a leisurely stroll along the waterfront at Deltaville Marina. This scenic location offers stunning views of the bay and is a great spot for fishing, kayaking, or simply soaking in the sun. Grab a bite to eat at nearby eateries and watch the boats come and go.
  • Deltaville Maritime MuseumOpens in a new window – Dive into the maritime history of the region at the Deltaville Maritime Museum. Discover fascinating exhibits showcasing the area's rich boat-building heritage and learn about the vibrant local culture. The museum hosts various events and activities, making it a lively stop for families and history enthusiasts alike.
  • Barrier Islands CenterOpens in a new window – Head to the Barrier Islands Center to explore the history and ecology of the unique barrier islands off the coast. This center offers engaging exhibits that delve into the region’s natural environment and the lifestyle of its inhabitants. Perfect for a day of discovery and learning!
  • Gwynn's Island Museum – Visit the Gwynn's Island Museum and uncover the intriguing history of this charming island community. The museum features exhibits that highlight the island's archaeology and anthropology, offering insights into the lives of those who have called this area home for generations. Engage with local artifacts and stories that bring the past to life.

5 tips for savvy savings when booking a hotel near Chesapeake Bay

  1. Book for the cheapest times: The most budget-friendly time to explore Chesapeake Bay is during January, February, and December, when hotel prices are lower. For a great value for money experience, a stay of at least 3 to 4 days is recommended to fully enjoy the area's significant landmarks, historical sites, and cultural experiences. Visitors can partake in various activities such as attending local festivals, watching soccer matches, visiting monuments, enjoying live music, and taking part in birdwatching and boating. This timeframe offers a wonderful opportunity to connect with friendly locals and immerse yourself in the rich history of the region. Hotel prices might drop during these months, making it an ideal choice for those on a budget.
  2. Look for last-minute deals on Hotels.com: To discover last-minute deals for a Chesapeake Bay beach vacation, visit the DealsOpens in a new window or Last-Minute DealsOpens in a new window sections on Hotels.com, where you may find discounted hotel rates close to your travel date. To stay informed about flash sales and special promotions, consider enabling email alerts or push notifications. Additionally, the Smart ShoppingOpens in a new window tool available via the app helps travelers compare hotel prices and amenities, making it easier to find the best options. This way, if rooms become available or prices drop, you’re more likely to see these updates first and book your 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 could help you save on your stay near a Chesapeake Bay hotel. If you're interested in unique accommodations, boutique hotels often provide a more personalized experience and may offer 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 the price is on the higher end, we’ll recommend more budget-friendly dates to increase your chances of finding a better deal.
  4. Consider your location: Staying near major attractions or city centers can be convenient, but it often comes with a higher price tag. If you're looking for more budget-friendly options, you might want to consider hotels in less central neighborhoods, striking a balance between cost and accessibility to the sites you plan to visit. Exploring independent hotels located a bit further out can also lead to a more authentic and usually more affordable experience.
  5. Become a Member: Join our membership for free and start planning your next getaway near Chesapeake Bay! Enjoy significant savings on over 100,000 hotels worldwide with exclusive member pricing. As a member, you'll have the opportunity to advance through our tiers, unlocking fantastic perks such as complimentary room upgrades (when available) and discounts on food and beverages at select VIP Access properties. Don't miss out on this chance to enhance your travel experience!

Best time to go to Chesapeake Bay

Chesapeake Bay 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. The peak travel months to visit Chesapeake Bay are April, July, and September, which see a higher number of tourists. During this peak period, the weather is mostly sunny, accompanied by light rainfall. In contrast, January, November, and December are ideal if you're looking for a calmer vacation, marked by light rainfall and mostly sunny conditions.

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