A golf course, a large building complex, and a marina by a river.

Book Chesapeake Bed & Breakfast

Check prices for these dates

Next weekend
Oct 2 - Oct 4
In two weeks
Oct 9 - Oct 11
In one month
Oct 23 - Oct 25
In two months
Nov 20 - Nov 22

Our top choices for Chesapeake bed & breakfast

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1. The Velvet Anchor | Chelsea Suite: Bohemian Charm

The Velvet Anchor | Chelsea Suite: Bohemian Charm
Norfolk
$175 nightly
The price is $204
Sep 24 - Sep 25
Total with taxes and fees
The Velvet Anchor | Chelsea Suite: Bohemian Charm
Front of property

2. The Inn at Four Eleven York

The Inn at Four Eleven York
4.0 star property
West Freemason
10.0 out of 10, Exceptional, (114 reviews)
"Great place!"
United States
Brian
$248 nightly
The price is $288
Oct 21 - Oct 22
Total with taxes and fees
The Inn at Four Eleven York
Front of property

3. Barclay Cottage

Barclay Cottage
3.5 star property
Northeast Virginia Beach
9.8 out of 10, Exceptional, (226 reviews)
"Amazing stay, we really enjoyed our time. It was lovely. Personable, clean, shared space but private. Loved it."
United States
Cadie
$136 nightly
The price is $159
Sep 23 - Sep 24
Total with taxes and fees
Barclay Cottage
Coffee/tea maker, fridge, microwave, oven

4. Cape Henry Full Suite Inn at Old Beach

Cape Henry Full Suite Inn at Old Beach
Northeast Virginia Beach
9.8 out of 10, Exceptional, (7 reviews)
"Private, and quiet, but seconds away from ocean"
United States
Blake F.
$425 nightly
The price is $490
Oct 13 - Oct 14
Total with taxes and fees
Cape Henry Full Suite Inn at Old 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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Top Chesapeake Hotel Reviews

Sandcastle Resort On The Beach

Sandcastle Resort On The Beach

10/10 Excellent
"Hotel staff was fantastic. 2 out of the 3 elevators were working, and this caused long waiting periods to get upstairs and downstairs. Ordered food from the restaurant, and nobody called to tell us it was ready resulting in soggy food. Not cool for what we paid. Hallways were dirty, but the rooms were ok; smaller than expected though. Furniture could stand to be updated as it was visibly damaged and falling apart. Some of the dresser drawers would hardly close. The batteries were dead in the safe. Aside from all of the above, we truly enjoyed our stay. Everyone we spoke with that worked at the hotel was fantastic and helpful. The location is great, and we were able to enjoy music from the restaurant below on our balcony. We had fun watching people get up early to get a morning surf in as well as watch the sun rise; truly spectacular. Pool was REALLY chlorinated, but we had a great time regardless. Awesome shower water pressure. We will definitely stay here again."
Jessica 3-night trip
Posted less than an hour ago
Sandcastle Resort On The Beach

Find out more about Chesapeake

Chesapeake B&B information

Number of reviews
226
Accommodation
8 B&B
Lowest Price
$159
Highest Price
$288

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 $159 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.

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