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Check prices for these dates

Next weekend
Jun 27 - Jun 29
In two weeks
Jul 4 - Jul 6
In one month
Jul 18 - Jul 20
In two months
Aug 15 - Aug 17

Compare 8 B&B in Chesapeake with updated reviews, rates, and availability.

Barclay Cottage B&B
Front of property - evening/night

Barclay Cottage B&B

3.5 star property
10.0 out of 10, Exceptional, (188)
"was absolutely wonderful, they made delicious beautiful breakfast for us, would 100% go again:)"
Barclay Cottage B&B
The Inn at Four Eleven York
Front of property

The Inn at Four Eleven York

4.0 star property
10.0 out of 10, Exceptional, (94)
"Lovely B&B, very comfortable, friendly staff. Would definitely stay again"
$271 nightly
The price is $315
Jun 22 - Jun 23
Total includes taxes and fees
The Inn at Four Eleven York
The Magnolia House Inn
Boating

The Magnolia House Inn

3.5 star property
9.2 out of 10, Wonderful, (46)
"The hospitality was phenomenal!! My husband and I felt so at home with the innkeepers Lankford and Joyce. The breakfast was EXCELLENT! We will DEFINITELY visit again."
The Magnolia House Inn
Extra large suite with balcony, private, bathroom, free parking
1 bedroom, iron/ironing board, free WiFi, bed sheets

Extra large suite with balcony, private, bathroom, free parking

Extra large suite with balcony, private, bathroom, free parking
The Teacherage
Exterior

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
The Pinner House
Romantic Room | 1 bedroom, individually decorated, individually furnished

The Pinner House

4.5 star property
The Pinner House
Charming 1-bedroom bed & breakfast resort in awesome Virginia Beach
Pool

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

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

What is the nightly rate for a Bed & Breakfast in Chesapeake?
Prices for B&Bs in Chesapeake often vary, but you can find a great deal from $315 with Expedia. All sorts of factors affect price, such as location and the time of year. It usually costs more to stay at Chesapeake B&Bs over the weekend too. Travelers can find the best deals by being flexible with their dates, and by using our filters to sort prices from low to high.
When is the best time to book a B&B in Chesapeake?
The best time to book a B&B in Chesapeake is during the spring months of April to June. This period draws visitors eager to enjoy the pleasant weather and vibrant natural beauty, with temperatures ranging from the mid-50s to mid-80s Fahrenheit. The region comes alive with blooming flowers and lush greenery, making it an ideal backdrop for outdoor activities such as kayaking, hiking, and exploring the scenic parks.
As the summer approaches, July becomes the most popular month for travelers. During this peak season, you'll find a buzzing atmosphere filled with families and friends enjoying Chesapeake's waterfront and local festivals. The warm temperatures are superb for engaging in water sports or relaxing by the bay.
For those looking to travel on a budget, consider visiting in December. This month offers a unique charm, as Chesapeake is beautifully decorated for the holiday season. It's a quieter time, allowing for a more intimate experience while enjoying local holiday events and cozy gatherings.
What is the difference between a Chesapeake B&B and a hotel?
Every Chesapeake B&B has its own unique feel. Whether it's a cozy reading space or a sunlit breakfast nook to enjoy your morning cup of coffee, the quaint details are what make bed and breakfasts a home away from home. Travelers can look forward to personal touches, thoughtful amenities and of course a scrumptious breakfast at Chesapeake B&Bs.