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5 Dec - 7 Dec
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12 Dec - 14 Dec
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26 Dec - 28 Dec
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23 Jan - 25 Jan

B&B in Chesapeake Beach

Exterior
George Brooks House B&B

George Brooks House B&B

3.0 star property
St. Michaels
8.6 out of 10, Excellent, (65)
"Gorgeous quaint historic house. Friendly owner, close to town "
United States
Christopher
The price is SAR 638
SAR 702 total
includes taxes & fees
1 Jan - 2 January 2026
George Brooks House B&B
Porch
Parsonage Inn

Parsonage Inn

3.5 star property
St. Michaels
9.2 out of 10, Wonderful, (130)
"Hosts were wonderful, breakfast was delicious, everything was walkable "
United States
Nathaly
The price is SAR 750
SAR 825 total
includes taxes & fees
1 Jan - 2 January 2026
Parsonage Inn
Full-size fridge, blender, toaster oven, waffle maker
Legacy Villa

Legacy Villa

4.0 star property
Upper Marlboro
The price is SAR 1,062
SAR 1,201 total
includes taxes & fees
2 Dec - 3 Dec
Legacy Villa
Horseback riding
The Inn at Tacaro Estate

The Inn at Tacaro Estate

5.0 star property
Tracys Landing
9.2 out of 10, Wonderful, (10)
"Amazing, warm, gracious setting. Can’t wait to return "
United States
Andrea
The Inn at Tacaro Estate
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.
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Top Chesapeake Beach Hotel Reviews

Sonesta ES Suites Annapolis

Sonesta ES Suites Annapolis

10/10 Excellent
"roomy and spacious"
DENNIS RYAN 1-night trip
Posted 5 days ago
Sonesta ES Suites Annapolis

Frequently asked questions

Searching for B&Bs in Chesapeake Beach?
If you're looking for something a little more offbeat than your standard hotel, a bed and breakfast could be the perfect alternative for your vacation. For any museum buff, a trip to Chesapeake Beach wouldn't be complete without a stop by Chesapeake Beach Railway Museum or Bruce Gabrielson's Surf Art Gallery and Museum.
Why consider B&Bs instead of traditional hotels?
With attentive service, opportunities to socialize with other guests, and hearty breakfasts, B&Bs offer a truly one-of-a-kind setting.
What are the top B&Bs in Chesapeake Beach?
Here are some B&Bs in the surrounding area: George Brooks House B&B: 6 rooms. 18 mi (28.9 km) from the heart of Chesapeake Beach. Enjoy the library and fireplace in the lobby. Parsonage Inn: 8 rooms. 17.9 mi (28.8 km) from the downtown core. Enjoy the free full breakfast and unique décor. The Inn at Tacaro Estate: 8 rooms. Situated 5.1 mi (8.2 km) from the heart of Chesapeake Beach. Enjoy the free full breakfast and designer toiletries. Legacy Villa: 2 rooms. 16.7 mi (26.9 km) from the heart of downtown. Enjoy the in-room pools and massage services. Black Walnut Point Inn: 7 rooms. Located 10.6 mi (17.1 km) from the core of Chesapeake Beach. Enjoy the free full breakfast and massage services.
What's the best time of year to stay at a B&B in Chesapeake Beach?
When you're dreaming of a getaway to Chesapeake Beach, be sure to take into account the year-round temperatures. The hottest months are usually July and August with an average temp of 75°F, while the coldest months are January and February with an average of 40°F. Average annual precipitation for Chesapeake Beach is 52 inches.
What is there to do in Chesapeake Beach?
Travelers enjoy Chesapeake Beach for its beaches and restaurants. Spend some time exploring Breezy Point Beach and Northern Chesapeake Bay if you're hoping to see some of the area's natural features. You might put Chesapeake Beach Water Park and Chesapeake Beach Railway Museum on your list if you want to see more of the area.
How can I get to and around Chesapeake Beach?
Planning your excursions in and around Chesapeake Beach is easier with these transportation options. Fly into Easton, MD (ESN-Easton - Newnam), which is located 26.5 mi (42.7 km) away from the heart of the city. Otherwise, look for flights into College Park, MD (CGS), which is 28.8 mi (46.3 km) away. If you'd like to venture out around the area, you may want a rental car for your journey.