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Check prices for these dates

Next weekend
May 9 - May 11
In two weeks
May 16 - May 18
In one month
May 30 - Jun 1
In two months
Jun 27 - Jun 29

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, (181)
"Beautiful stay and the breakfast was wonderful. Every day was something different and delicious. Would highly recommend."
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, (90)
"All staff was incredibly kind and helpful. I will absolutely stay here again. "
The price is $287
includes taxes & fees
$247 per night
May 6 - May 7
The Inn at Four Eleven York
King B&B room 1 hour from the OBX & Hampton Roads
Outdoor dining

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

7.4 out of 10, Good, (6)
"Everything was as advertised. Nice and comfortable place to stay."
The price is $160
includes taxes & fees
$142 per night
May 5 - May 6
King B&B room 1 hour from the OBX & Hampton Roads
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 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
The Teacherage
Sports facility

The Teacherage

2.5 star property
7.4 out of 10, Good, (56)
The Teacherage
Beach Spa Bed and Breakfast
Outdoor spa tub

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 | Individually decorated, individually furnished, blackout drapes

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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Other property types in Chesapeake

The Ocean Key Virginia Beach Resort
Indoor pool

The Ocean Key Virginia Beach Resort

3.0 star property
7.8 out of 10, Good, (1318)
"Would love to visit again. Maybe longer next time! "
The price is $162
includes taxes & fees
$139 per night
May 14 - May 15
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, (1047)
"very nice place"
The price is $162
includes taxes & fees
$139 per night
May 27 - May 28
Ocean Sands Resort, Oceanfront, Virginia Beach by Vacatia
The Atrium Resort, Virginia Beach by Vacatia
Beach nearby

The Atrium Resort, Virginia Beach by Vacatia

3.5 star property
8.2 out of 10, Very Good, (1324)
"Location is great close to beach nice places to eat nearby."
The price is $152
includes taxes & fees
$131 per night
May 15 - May 16
The Atrium Resort, Virginia Beach by Vacatia
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 Chesapeake Arboretum 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: Barclay Cottage B&B: 5 rooms. 17.9 mi (28.8 km) from the heart of Chesapeake. Enjoy the free full breakfast and onsite spa services. The Inn at Four Eleven York: 4 rooms. 5.9 mi (9.6 km) from the downtown core. Enjoy the free cooked breakfast and designer toiletries. 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 Oak Grove Lake Park 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.