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Check prices for these dates

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15 Aug - 17 Aug
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5 Sept - 7 Sept
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Barclay Cottage B&B
Experience a traditional bed and breakfast stay with a welcoming porch and classic architectural style.

Barclay Cottage B&B

3.5 star property
10.0 out of 10, Exceptional, (192)
"was absolutely wonderful, they made delicious beautiful breakfast for us, would 100% go again:)"
Barclay Cottage B&B
The Inn at Four Eleven York
Welcome to Four Eleven York Street, a boutique inn with a historic entrance featuring a bay window and turret.

The Inn at Four Eleven York

4.0 star property
10.0 out of 10, Exceptional, (95)
"Lovely B&B, very comfortable, friendly staff. Would definitely stay again"
The Inn at Four Eleven York
The Magnolia House Inn
Boats dock at the marina, surrounded by the calm waters of the pier.

The Magnolia House Inn

3.5 star property
9.2 out of 10, Wonderful, (48)
"Wonderful B&B! The owners are beyond hospitable and the breakfast is out of this world. The location itself is central to many restaurants and shops, a quick walk or lyft will get you anywhere you need to be. The B&B itself has been beautifully restored and maintained. Highly recommend!"
The Magnolia House Inn
The Teacherage
Expansive indoor space with high ceilings and large windows.

The Teacherage

2.5 star property
7.4 out of 10, Good, (56)
The Teacherage
Beach Spa Bed and Breakfast
Property grounds

Beach Spa Bed and Breakfast

4.0 star property
9.0 out of 10, Wonderful, (258)
Beach Spa Bed and Breakfast
Charming 1-bedroom bed & breakfast resort in awesome Virginia Beach
Relax by the serene pool surrounded by lush greenery and a tranquil view.

Charming 1-bedroom bed & breakfast resort in awesome Virginia Beach

Charming 1-bedroom bed & breakfast resort in awesome Virginia Beach
The Pinner House
1 bedroom, individually decorated, individually furnished

The Pinner House

4.5 star property
The Pinner House
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 Hotel Reviews

Oceanfront Inn

Oceanfront Inn

10/10 Excellent
"Property was clean and well maintained. "
RONALD 3-night trip
Posted 9 hours ago
Oceanfront Inn

Frequently asked questions

Searching for B&Bs in Chesapeake?
If you want to find some accommodation with fewer rooms than a hotel and a more personalised environment, a B&B might be the perfect option for your holiday to Chesapeake. If your ideal holiday to Chesapeake includes spending lots of time outside, Chesapeake City Park and Crestwood Park are good spots to enjoy the scenery.
Are you thinking about an apartment instead of a traditional hotel?
With attentive service, opportunities to interact with the owner and of course a full breakfast to start the day, B&Bs provide a truly one-of-a-kind setting.
What are the best B&Bs in Chesapeake?
Below are some well-liked B&Bs in the area: Barclay Cottage B&B: 5 rooms. 17.9 mi (28.8 km) from the heart of Chesapeake. Enjoy the free full breakfast and on-site spa services. The Inn at Four Eleven York: 4 rooms. 5.9 mi (9.6 km) from the city centre. Enjoy the free cooked breakfast and designer toiletries. The Magnolia House Inn: 3 rooms. Situated 18 mi (28.9 km) from the heart of Chesapeake. Enjoy the free full breakfast and designer toiletries. Beach Spa Bed and Breakfast: 8 rooms. Located 18 mi (28.9 km) from the core of Chesapeake. Enjoy the free full breakfast and designer toiletries.
When is the best time to book my B&B in Chesapeake?
When you're dreaming of a getaway to Chesapeake, year-round temperatures and rainfall may be important factors to consider. The hottest months are usually July and August, with an average temperature of 25°C, while the coldest months are January and February, with an average of 7°C. Average annual precipitation for Chesapeake is 1359 mm.
What is there to do in Chesapeake?
Travellers enjoy Chesapeake for its beautiful beaches and major shopping area. When you want to spend some time in the great outdoors, Chesapeake City Park and Oak Grove Lake Park are some notable spots. You should put Greenbrier Mall and Chesapeake Conference Center on your list if you want to see more of the area.
How can I get to and around Chesapeake?
Mapping out your trip in and around Chesapeake is easy with these transportation options. Fly into Norfolk, VA (ORF-Norfolk Intl.), which is located 10.1 mi (16.3 km) from the heart of the city. Otherwise, you can search for flights to Newport News, VA (PHF-Newport News - Williamsburg Intl.), which is 27.6 mi (44.5 km) away. If you'd like to explore around the area, you may want to rent a car for your trip.