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Our top choices for Chesapeake Bay hotels

A wooden rocking chair on a porch with a view of a field and a building in the background.

1. Shore Stay Suites

Shore Stay Suites
2.0 star property
36 km from Chesapeake Bay
8.2 out of 10, Very good, (747 reviews)
"Room was very clean, beds were comfortable. Like that it had a full size refrigerator and kitchenette."
United States
Carol
The price is CA $148
CA $165 total
includes taxes & fees
Nov 23 - Nov 24
Shore Stay Suites
A resort with a swimming pool, a dock, and a large building.

2. The Tides Inn

The Tides Inn
4.0 star property
33 km from Chesapeake Bay
9.0 out of 10, Wonderful, (187 reviews)
"Great location, amazing service, will be back!"
United States
Dan
The price is CA $352
CA $448 total
includes taxes & fees
Nov 29 - Nov 30
The Tides Inn
A hotel room with a large bed, a desk, a vanity with a mirror, a red lamp, and framed pictures on the wall.

3. Quality Inn & Suites

Quality Inn & Suites
2.0 star property
39.1 km from Chesapeake Bay
7.0 out of 10, Good, (962 reviews)
"The room was very clean and comfortable. I arrived after midnight and April was very helpful. Would definitely stay here again"
United States
Heather
The price is CA $113
CA $121 total
includes taxes & fees
Nov 9 - Nov 10
Quality Inn & Suites
A hotel room with a kitchenette, a seating area with a sofa and armchair, and a large window with curtains.

4. Hampton Inn & Suites Exmore - Eastern Shore

Hampton Inn & Suites Exmore - Eastern Shore
2.5 star property
24.2 km from Chesapeake Bay
8.2 out of 10, Very good, (1,003 reviews)
"We had a great stay!"
United States
Amanda
The price is CA $115
CA $128 total
includes taxes & fees
Nov 14 - Nov 15
Hampton Inn & Suites Exmore - Eastern Shore
Exterior

5. Holiday Inn Express & Suites Exmore - Eastern Shore by IHG

Holiday Inn Express & Suites Exmore - Eastern Shore by IHG
2.5 star property
24.1 km from Chesapeake Bay
8.4 out of 10, Very good, (882 reviews)
"Breakfast included in room cost was outstanding!!"
United States
margaret
The price is CA $143
CA $159 total
includes taxes & fees
Nov 12 - Nov 13
Holiday Inn Express & Suites Exmore - Eastern Shore by IHG
A reception area with a wooden counter, a clock, a framed map, and a vintage suitcase labeled "the Charlotte".

6. The Charlotte Hotel & Restaurant

The Charlotte Hotel & Restaurant
3.5 star property
37.9 km from Chesapeake Bay
9.0 out of 10, Wonderful, (334 reviews)
"We loved staying here. It was very unfortunate the restaurant was closed when we were there but there were many other good options within walking distance. The hotel was clean, charming, homey, and we loved the decor and overall vibe of the place. This was my favorite place to stay on our trip and I hope we can visit and stay again someday."
United States
Holly
The price is CA $201
CA $222 total
includes taxes & fees
Nov 9 - Nov 10
The Charlotte Hotel & Restaurant
A Holiday Inn Express & Suites building with a covered entrance and a brick facade.

7. Holiday Inn Express Gloucester by IHG

Holiday Inn Express Gloucester by IHG
3.5 star property
39.7 km from Chesapeake Bay
7.2 out of 10, Good, (760 reviews)
"The staff was very nice"
United States
Jackie
The price is CA $120
CA $134 total
includes taxes & fees
Dec 7 - Dec 8
Holiday Inn Express Gloucester by IHG
A large white house with a dark roof, multiple chimneys, and a white fence in the foreground.

8. Warner Hall

Warner Hall
3.0 star property
38.4 km from Chesapeake Bay
10.0 out of 10, Exceptional, (48 reviews)
"Outstanding all around"
United States
Brandon
The price is CA $314
CA $349 total
includes taxes & fees
Nov 9 - Nov 10
Warner Hall
A hotel lobby with a reception desk, chairs, a fruit bowl, framed pictures, and a waste bin.

9. Hampton Inn Gloucester

Hampton Inn Gloucester
2.5 star property
39.7 km from Chesapeake Bay
9.2 out of 10, Wonderful, (812 reviews)
"Property met standards for Hampton Inn."
United States
Debra
The price is CA $143
CA $159 total
includes taxes & fees
Nov 15 - Nov 16
Hampton Inn Gloucester
A spacious lobby with a high ceiling, a chandelier, a dining area with a table and chairs, and a large window providing natural light.

10. Quality Inn & Suites Exmore - Eastern Shore

Quality Inn & Suites Exmore - Eastern Shore
2.5 star property
25.4 km from Chesapeake Bay
7.2 out of 10, Good, (791 reviews)
"The room smelled like a wet dog. The shower curtain and shampoo dispensers were soiled. The staff were very friendly."
United States
Patricia
The price is CA $114
CA $127 total
includes taxes & fees
Dec 7 - Dec 8
Quality Inn & Suites Exmore - Eastern Shore
A bedroom with a wooden ceiling, a bed with white and gray bedding, a wall-mounted shelf with decorative items, and a window with blinds.

11. Cape Charles Tiny Livin

Cape Charles Tiny Livin
2.0 star property
29.4 km from Chesapeake Bay
9.6 out of 10, Exceptional, (28 reviews)
"Great place. Perfect for traveling with our two small pups."
United States
Jennifer
Cape Charles Tiny Livin
A hotel room with two beds, a desk, a chair, and a television.

12. Quality Inn Kilmarnock

Quality Inn Kilmarnock
2.5 star property
33.9 km from Chesapeake Bay
7.6 out of 10, Good, (795 reviews)
"Room was clean and well stocked with everything, staff was friendly, a.c. worked well and there was ample parking."
United States
Terri
The price is CA $146
CA $166 total
includes taxes & fees
Nov 10 - Nov 11
Quality Inn Kilmarnock
A small, single-story house with a porch and a covered front porch area.

13. Grey's Point Camp

Grey's Point Camp
3.0 star property
31.1 km from Chesapeake Bay
9.2 out of 10, Wonderful, (25 reviews)
"We really enjoyed our stay!"
United States
Sheri
Grey's Point Camp
A room with a view of the ocean through a large window, a white door, and a white railing outside.

14. The Baywood Bed & Breakfast

The Baywood Bed & Breakfast
3.0 star property
43.2 km from Chesapeake Bay
9.8 out of 10, Exceptional, (226 reviews)
"Had an awesome stay. Clean, quiet and amazing view of the bay"
United States
Jelani
The price is CA $274
CA $305 total
includes taxes & fees
Dec 7 - Dec 8
The Baywood Bed & Breakfast
A spacious hallway with a grand staircase, wooden flooring, and a large ornate rug.

15. Hornsby House Inn

Hornsby House Inn
3.0 star property
47.8 km from Chesapeake Bay
10.0 out of 10, Exceptional, (75 reviews)
"Great location and wonderful staff."
United States
Bryan
The price is CA $305
CA $345 total
includes taxes & fees
Nov 9 - Nov 10
Hornsby House Inn
A hotel lobby with a reception desk, a large fish decoration on the wall, and various items displayed on shelves.

16. Wachapreague Inn

Wachapreague Inn
3.0 star property
37.8 km from Chesapeake Bay
9.2 out of 10, Wonderful, (117 reviews)
"The Wachapreague Inn is a quaint, local treasure that is quiet and clean. We enjoyed our stay and the staff was incredibly kind and accommodating. The room was clean, the beds were soft, and they have great hot water! The town itself is very small and quiet. We were only in town for one night, but we hope to come back another time to stay longer and explore."
United States
Chelsea
The price is CA $177
CA $195 total
includes taxes & fees
Nov 9 - Nov 10
Wachapreague Inn
A sunlit room with large windows, a wooden sofa, a red chair, and a Christmas tree.

17. Whispering Pines by Hotel O Whitestone VA

Whispering Pines by Hotel O Whitestone VA
2.5 star property
29.3 km from Chesapeake Bay
6.0 out of 10, (168 reviews)
"Though it is obvious that money is tight and some maintenance and ambiance needs have been put on hold, the staff couldn’t have been more helpful and pleasant. It was a much lower price than other places to stay, and I enjoyed my time there."
United States
Ellen
The price is CA $123
CA $145 total
includes taxes & fees
Nov 9 - Nov 10
Whispering Pines by Hotel O Whitestone VA
Exterior

18. Bay Tree Manor

Bay Tree Manor
2.0 star property
45 km from Chesapeake Bay
10.0 out of 10, Exceptional, (6 reviews)
"We enjoyed the wonderful view of the water, excellent breakfast and hospitality of the owners."
United States
Dave
Bay Tree Manor
A hotel room with a bed, bedside table, desk, chair, and a mirror.

19. Budget Inn

Budget Inn
2.0 star property
22.6 km from Chesapeake Bay
6.2 out of 10, (254 reviews)
"BAD PROPERTY"
United States
MARK
The price is CA $99
CA $134 total
includes taxes & fees
Nov 9 - Nov 10
Budget Inn
A small building with a sign reading "Regal Inn" and a set of stairs leading to the entrance.

20. Regal Inn

Regal Inn
2.0 star property
38.5 km from Chesapeake Bay
5.8 out of 10, (113 reviews)
"The Regal Inn staff was quite helpful. Despite my last minute last accomodation request i 1during my road trip journey."
United States
Silca
Regal Inn
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties

Compare popular hotels close to Chesapeake Bay

Property
Star rating
Guest rating
Breakfast included
Pool
Spa
Pet-friendly
WiFi included
Exterior
Holiday Inn Express & Suites Exmore - Eastern Shore by IHG
2.5 star property
8.4
Very good
882 reviews
View
A hotel room with a kitchenette, a seating area with a sofa and armchair, and a large window with curtains.
Hampton Inn & Suites Exmore - Eastern Shore
2.5 star property
8.2
Very good
1,003 reviews
View
A bedroom with a bed, a bedside table, a lamp, a TV, and a window.
Dockside Inn
3.0 star property
9.4
Exceptional
57 reviews
View
A spacious lobby with a high ceiling, a chandelier, a dining area with a table and chairs, and a large window providing natural light.
Quality Inn & Suites Exmore - Eastern Shore
2.5 star property
7.2
Good
791 reviews
View
A hotel lobby with a reception desk, a large fish decoration on the wall, and various items displayed on shelves.
Wachapreague Inn
3.0 star property
9.2
Wonderful
117 reviews
View

Other attractions near Chesapeake Bay

Horse Island

Commune with nature and explore the great outdoors at Horse Island during your travels in Machipongo. Take in the museums while you're in the area.
See properties

Top Chesapeake Bay Hotel Reviews

A two-story house with a porch, a front door, and a small garden area.
The Wildset

The Wildset

The Wildset
Downtown St. Michaels

10/10 Excellent

Our stay at the Wildset was amazing! The room was beautiful and clean. The staff were available at all hours and did the most to ensure our stay was special. The hotel has lots of small touches that truly make the experience like bikes, a cafe with coffee and drinks, and smore's kits in the evenings.
Canada
Mairi
Reviewed August 11, 2026
The Wildset

Find out more about Chesapeake Bay

Top reasons to visit Chesapeake Bay

  • Stunning Water Views: Experience breathtaking scenery along the Chesapeake Bay, featuring beautiful beaches and marinas.
  • Outdoor Adventures: Enjoy a range of recreational activities, from exploring nature reserves to beach days.
  • Charming Coastal Towns: Discover unique towns with rich history and friendly atmospheres, perfect for leisurely strolls.
  • Family-Friendly Environment: The region caters to families, offering activities that everyone can enjoy.
  • Diverse Accommodations: Choose from a variety of lodging options, including waterfront hotels and agritourism stays.

Find great hotels near Chesapeake Bay

Experience the charm of Chesapeake Bay with a variety of hotel accommodations tailored for every type of traveller. From family-friendly options to pet-friendly stays, you'll find the perfect place to unwind after a day of adventure. Whether you're looking for waterfront hotels or unique agritourism properties, Chesapeake Bay offers an array of inviting choices to make your vacation memorable.

  • Holiday Inn Express and Suites Exmore, Eastern Shore by IHG: This hotel offers a modern and welcoming atmosphere, ideal for business travellers seeking a convenient stay near Chesapeake Bay. Located 24.1km from the bay, the property is LGBTQIA-friendly, making it a safe and inclusive choice for all guests. With multiple meeting rooms and accessible business centres, it’s perfect for those needing to conduct meetings or work remotely. Guests can enjoy complimentary breakfast and high-speed Wi-Fi, ensuring a productive and comfortable stay.
  • Hampton Inn & Suites Exmore - Eastern Shore: Just 24.1km from Chesapeake Bay, this pet-friendly hotel is known for its warm hospitality and inclusive environment. Ideal for families and pet owners, the Hampton Inn & Suites welcomes dogs and cats, with a waived fee for service animals. Guests can unwind in comfortable rooms, enjoy a complimentary hot breakfast, and take advantage of the fitness centre and indoor pool. This hotel strikes a balance between leisure and convenience, making it an excellent choice for a relaxing getaway.
  • Quality Inn & Suites: Located 25.7km from Chesapeake Bay, Quality Inn & Suites combines business amenities with a pet-friendly policy, catering to both working travellers and families. This hotel allows dogs, and guests benefit from waived fees for service animals, ensuring a comfortable stay for all. With accessible meeting facilities and a supportive environment for business needs, it is well-suited for professionals on the go. Guests can enjoy complimentary breakfast and spacious accommodations, creating a convenient base for their adventures.

Where to stay near Chesapeake Bay

Chesapeake Bay offers an unforgettable vacation experience filled with stunning water views, beautiful beaches, and a friendly atmosphere. Whether you're exploring charming coastal towns or relaxing along the shoreline trail, you'll find a perfect blend of history and natural beauty. The region's family-friendly vibe makes it ideal for outdoor adventures and leisurely beach days, allowing you to enjoy the best of both worlds in a picturesque setting.

  • Silver Beach: Nestled a mere 12.9km from the enchanting Chesapeake Bay, Silver Beach is a charming village that offers a delightful mix of outdoor and family-friendly experiences. With traveller arrivals peaking from June to August, this locale boasts a vibrant boardwalk and scenic recreational areas, making it a popular destination for those eager to soak up the sun and enjoy nature. Visitors can explore nearby attractions such as the beautiful beach and nature reserve, perfect for a day of relaxation or family fun.
  • Gwynn: Located approximately 16.1km from Chesapeake Bay, the city of Gwynn draws visitors with its rich cultural heritage and beautiful outdoor settings. Peak travel seasons from May to July bring a lively atmosphere to the area. Enjoy activities at the local golf course, or take a leisurely stroll along the boardwalk. Cultural enthusiasts will appreciate the nearby museum dedicated to archaeology and anthropology, providing a glimpse into the region's historical significance alongside the stunning beach that invites beachgoers and nature lovers alike.
  • Jamesville: Situated 16.1km from Chesapeake Bay, the village of Jamesville is a hidden gem, especially popular during the spring and early summer months. Renowned for its adventurous outdoor experiences, visitors can explore scenic hiking trails and recreation parks. The stunning beaches and the nearby national state park offer ample opportunities for outdoor adventures, making it an ideal spot for those looking to connect with nature and enjoy some thrilling activities. While summer brings the crowds, the tranquil atmosphere during off-peak months provides a peaceful retreat.

Things to do near Chesapeake Bay

Chesapeake Bay is perfect for outdoor and beach vacations, offering stunning scenery and a range of activities. Visitors can explore the boardwalk, enjoy recreational areas, and discover picnic spots. Don't miss the chance to look for resorts and participate in resort activities, as well as visit the Chesapeake Adventure Park. Additionally, there are various event venues to enhance your experience and create lasting memories during your stay.

Shopping

For a delightful shopping experience in Chesapeake Bay, visit the Northampton Shopping Center, 24.1km away, offering a mix of entertainment and family vibes. Explore the Blue Crow Antique Mall, 30.6km away, for unique finds, or head to Riverwalk Landing, 48.3km away, for a charming shopping atmosphere.

Recreation

Golden Eagle Golf Club offers a splendid outdoor golfing experience, 32.2km from Chesapeake Bay, surrounded by nature. For relaxation, visit Gloucester Point Beach Park, 46.7km away, where you can unwind by the water. Eastern Shore Yacht and Country Club Golf Course, 29.0km from Chesapeake Bay, provides another fantastic golfing option.

Adventure

Experience thrilling water sports at SouthEast Expeditions, located 37.0km from Chesapeake Bay, where you can enjoy kayaking and stand-up paddleboarding amidst beautiful scenery. For a fun challenge, head to Back Creek Park Tennis Center, 46.7km away, offering excellent courts and a vibrant atmosphere for tennis enthusiasts.

Nightlife

Experience the vibrant nightlife at the North Street Playhouse, a charming theatre located 37.0km from Chesapeake Bay. Enjoy a mix of culture and romance in an entertaining atmosphere, perfect for families and couples alike seeking a memorable evening out.

*Distances are measured in a straight line; actual driving distances may vary depending on the route.

Booking tips and Expedia advantages for Chesapeake Bay

To save money on your Chesapeake Bay vacation, consider visiting between December and February, when accommodation prices are lower. Avoid weekends, especially Saturdays, as Tuesday is typically the least expensive day for stays. Use Expedia’s search tool to find budget-friendly options, and remember to filter by price from lowest to highest. Combining your hotel booking with flights and activities through an Expedia package can also yield great savings. Look for upfront pricing and deals on cheap hotels to maximise your budget while enjoying free activities in the beautiful bay area.

  • The most and least expensive months on average to stay in a hotel: The cheapest months to stay around Chesapeake Bay are December to February, where the prices are slightly lower. This is in comparison to June to August, where prices are slightly higher.
  • The most and least expensive days on average to stay in a hotel: The least expensive day to stay around Chesapeake Bay is Tuesday. The most expensive day to stay around Chesapeake Bay is Saturday.
  • Find cheap hotels on Expedia: Utilize Expedia’s search tool to refine your options based on your budget, preferred location, and desired hotel type. To discover the best prices and deals, simply arrange the price filter from lowest to highest.
  • Consider bundling your trip: You can potentially save some money by combining your Chesapeake Bay hotel reservation with your flights and activities through an Expedia package.

Find the best attractions near Chesapeake Bay

Chesapeake Bay offers a perfect getaway for outdoor enthusiasts, beach lovers, and culture seekers alike. Popular attractions include the Chesapeake Arboretum, the iconic Chesapeake Bay Bridge, and the stunning Eastern Shore. With its beautiful beaches, marinas, and nature reserves, visitors can immerse themselves in the area's natural splendour while exploring key sites that showcase the charm of Chesapeake Bay, Virginia.

  • Deltaville Marina: Located 19.3km from Chesapeake Bay, Deltaville Marina offers a vibrant outdoor adventure experience. Enjoy the tranquil waters, perfect for boating and fishing, while soaking in the relaxed beach vibes that make this spot a local favourite.
  • Gwynn's Island Museum: Situated 16.1km away, this museum immerses visitors in the rich cultural heritage of the region. Explore fascinating archaeological and anthropological exhibits that showcase the area's history and community, providing a unique insight into local life.
  • Cape Charles Beach: Just 29.0km from Chesapeake Bay, Cape Charles Beach is a picturesque destination for sunbathing and swimming. With its soft sands and stunning views, it’s the ideal spot to unwind and enjoy a quintessential beach day.

Best time to go to Chesapeake Bay

The best time to visit Chesapeake Bay is dependant on what kind of holiday you are seeking. July is its hottest month on average. At this time, visitor numbers are slightly high and weather is mostly sunny with light rain. January is its coolest month on average. At this time, visitor numbers are slightly low and weather is mostly sunny with light rain.

Calendar MonthTemperaturePrecipitationCloudinessOccupancyPricing
January38.7°F (3.7°C)Light RainMostly SunnySlightly LowSlightly Low
February42.1°F (5.6000000000000005°C)Light RainMostly SunnyAverageSlightly Low
March45.3°F (7.4°C)Light RainMostly SunnyAverageAverage
April57.9°F (14.4°C)Light RainMostly SunnySlightly HighAverage
May66.6°F (19.200000000000003°C)Light RainMostly SunnyAverageAverage
June74.8°F (23.8°C)Light RainMostly SunnyAverageSlightly High
July79.5°F (26.4°C)Light RainMostly SunnySlightly HighSlightly High
August77.9°F (25.5°C)Light RainMostly SunnyAverageSlightly High
September72.7°F (22.6°C)Light RainMostly SunnySlightly HighAverage
October62.8°F (17.1°C)Light RainMostly SunnyAverageAverage
November51.4°F (10.8°C)Light RainMostly SunnySlightly LowAverage
December40.5°F (4.7°C)Light RainMostly SunnySlightly LowSlightly Low

The nearest major airports for your trip to Chesapeake Bay

When visiting Chesapeake Bay, you can fly into several major airports. Richmond International Airport (RIC) is 107.8km away, with nearby hotels such as The Jefferson Hotel and Omni Richmond Hotel, both around 6 to 11.3km from the airport. Norfolk International Airport (ORF), located 69.2km away, offers accommodations like Delta Hotels by Marriott Virginia Beach Waterfront and The Westin Virginia Beach Town Center, approximately 6 to 12.9km from the airport. Lastly, Newport News-Williamsburg International Airport (PHF) is 54.7km from Chesapeake Bay, with options like DoubleTree by Hilton Williamsburg and Kingsmill Resort, both about 19.3km from the airport.

Frequently Asked Questions

When is the best time to go to Chesapeake Bay?

The most popular time to visit Chesapeake Bay is during the summer months, particularly in July. This peak season sees average temperatures ranging from 24 to 30°C, creating an friendly space for outdoor adventures such as boating, fishing, and exploring the scenic waterfront. The warm weather also enhances your experience of the Bay's charming coastal towns and vibrant local festivals.

From July to September, the area buzzes with activity, making it a great time for those who enjoy a lively environment filled with tourists and locals alike. You can indulge in fresh seafood at outdoor dining spots while taking in the picturesque views, or join in on various events that celebrate the region's rich maritime heritage.

For families seeking memorable experiences, the summer is ideal for beach trips, kayaking excursions, and nature walks along the many trails that weave through the stunning landscapes. The long daylight hours allow for extended adventures, ensuring you make the most of your time in this beautiful area.

If you’re looking for a more budget-friendly option, consider visiting in late September or October. This period offers milder temperatures, around 18 to 24°C, and a quieter atmosphere, making it an excellent time for those who prefer a more relaxed pace while still enjoying the region's natural beauty. Plus, you’ll have the chance to experience the stunning fall foliage, which adds a breathtaking backdrop to your adventures.

Can I cancel my hotel reservation on Expedia?

You can cancel your hotel reservation on Expedia, though it depends on the cancellation policy of your booking. Most bookings are refundable if canceled within 24-48 hours of the scheduled arrival. Be sure to check your booking confirmation for the exact cancellation policy. If free cancellation is available, you can cancel directly through your Expedia account by logging in, going to "My Trips", and selecting your reservation. To find flexible deals, filter your search by "Fully refundable property" for hotels in Chesapeake Bay.

How can I save on a Chesapeake Bay hotel booking with Expedia?

With Expedia, you’ll unlock our lowest prices by becoming a member. It’s free and easy to join, and you can even access member perks too. Just remember to sign in to get our best prices on Chesapeake Bay hotels. Another way to save is by booking your hotel and flights together on Expedia, where bundling can lead to significant savings.

How much is the nightly rate at a Chesapeake Bay hotel?

Prices for hotels in Chesapeake Bay often vary, but you can find a great deal from CA $114 on Expedia. All sorts of factors affect price, such as the time of year or the days of the week you choose for your stay. Find the best deals by being flexible with your dates, and sort search results by "Price: low to high" for the cheapest rate.