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Check prices for these dates

Next weekend
28 Feb - 2 Mar
In two weeks
7 Mar - 9 Mar
In one month
21 Mar - 23 Mar
In two months
18 Apr - 20 Apr

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

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, (85)
"Place was really nice and the staff was awesome. Food was so great. "
The price is AED 823
AED 958 total
includes taxes & fees
27 Feb - 28 Feb
The Inn at Four Eleven York
King B&B room 1 hour from the OBX & Hampton Roads
Room

King B&B room 1 hour from the OBX & Hampton Roads

7.4 out of 10, Good, (6)
"Day before we.arrived got a message our room.was to be changed . Had to share a bathroom It.was not.between rooms. It..was.down.the hall. Sometimes the wait.was a bit much. No.grounded electrical outlets in room While resting, housekeeper had to come.to.our room.twice in.30 min period to get.supplies for other roo.s"
The price is AED 301
AED 589 total
includes taxes & fees
17 Mar - 18 Mar
King B&B room 1 hour from the OBX & Hampton Roads
Barclay Cottage B&B
Room

Barclay Cottage B&B

3.5 star property
10.0 out of 10, Exceptional, (177)
"Incredible, the Hostess and Host were very nice people. Love them!!!"
Barclay Cottage B&B
The Magnolia House Inn
Front of property

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
The Teacherage
Exterior

The Teacherage

2.5 star property
7.4 out of 10, Good, (56)
"Difficult to find at night. Would have liked lamp At bedside "
The Teacherage
Extra large suite with balcony, private, bathroom, free parking
Room

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

Extra large suite with balcony, private, bathroom, free parking
The Pinner House
Front of property

The Pinner House

4.5 star property
The Pinner House
Beach Spa Bed and Breakfast
Front of property

Beach Spa Bed and Breakfast

4.0 star property
9.0 out of 10, Wonderful, (258)
"Literally needed a police escort to leave this place due to a situation with a fight that led to some drunk friend of the innkeeper following us to our Suite screaming at us. We had to lock ourselves in the room... We never met the actual innkeeper Tina. She was nowhere to be found. We met Kyle who PORTRAYED himself as the innkeeper. During our entire stay, there were constantly random people coming in and out of the innkeeper's apartment at all hours of the day. And on the last night of our...
Beach Spa Bed and Breakfast
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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Other property types in Chesapeake

The Ocean Key Virginia Beach Resort
Exterior

The Ocean Key Virginia Beach Resort

3.0 star property
7.8 out of 10, Good, (1290)
"Been here 3 times now and every time the staff is always helpful and just super nice. Overall just a really good team "
The price is AED 267
AED 526 total
includes taxes & fees
12 Mar - 13 Mar
The Ocean Key Virginia Beach Resort
Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia
Exterior

Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia

3.0 star property
8.0 out of 10, Very Good, (1437)
"Great place but need more bigger park spaces for guess"
The price is AED 379
AED 654 total
includes taxes & fees
26 Feb - 27 Feb
Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia
4X4 only! Canal front. Ocean AND sound views! Decks and porches on all levels.
Saturday night dance party

4X4 only! Canal front. Ocean AND sound views! Decks and porches on all levels.

9.8 out of 10, Exceptional, (98)
"Our family of 4 enjoyed a quiet time in the outer banks at this lovely beach house. November isn't exactly the time most folks visit the beach, but we've spent most of our lives in the far north, so the "chilly weather" didn't prevent us from enjoying kayaking in the inner channels and viewing the sunset from the crow's nest. We found the kitchen very adequate; we were able to cook a lovely thanksgiving dinner and ate quite well the entire time. We packed all our needs/food for the weekend so...
4X4 only! Canal front. Ocean AND sound views! Decks and porches on all levels.
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.

Frequently asked questions

Searching for B&Bs in Chesapeake?
If you want to find an accommodation with fewer rooms than a hotel and an intimate environment, a B&B might be just the right fit for your vacation to Chesapeake. If your ideal vacation to Chesapeake includes spending lots of time outside, Chesapeake City Park and Great Dismal Swamp National Wildlife Refuge are good spots to enjoy the scenery.
Are you thinking about a B&B for your stay?
With attentive service, opportunities to socialize with other guests, 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: The Inn at Four Eleven York: 4 rooms. 5.9 mi (9.6 km) from the heart of Chesapeake. Enjoy the free cooked breakfast and designer toiletries. Barclay Cottage B&B: 5 rooms. 17.9 mi (28.8 km) from the downtown core. Enjoy the free full breakfast and onsite spa services. The Magnolia House Inn: 3 rooms. Located 18 mi (28.9 km) from the core of Chesapeake. Enjoy the free full breakfast and designer toiletries.
What's the best time of year to book my B&B in Chesapeake?
When you’re planning your stay in Chesapeake, be sure to take into account the year-round temperatures. The hottest months are usually July and August with an average temp of 77°F, while the coldest months are January and February with an average of 45°F. Average annual precipitation for Chesapeake is 54 inches.
What is there to do in Chesapeake?
Travelers 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 Great Dismal Swamp National Wildlife Refuge are some notable spots. You might 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?
You can plan your excursions in and around Chesapeake ahead of time with these transportation options. Fly into Norfolk Intl. Airport (ORF), which is located 10.1 mi (16.3 km) away from the city center. You can also search for flights into Newport News - Williamsburg Intl. Airport (PHF), which is 27.6 mi (44.5 km) away. If you’d like to explore around the area, you may want a rental car for your journey.