Compare Chesapeake Guest House Rentals

Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels

Save 10% or more on select hotels with Insider Prices

Book on the app to instantly earn 5% on 350,000+ hotels

Featured Guest Houses in Chesapeake

Country Escape Next DOOR Rental - Sleeps 6 - Stay upstairs in the trees

Guests staying at this guesthouse have access to laundry facilities, a garden, and barbecue grills.

Pet friendly

Free WiFi

Guests staying at this guesthouse have access to a garden and barbecue grills.

Free WiFi

Air conditioning

Guests of this guesthouse enjoy access to a water park, laundry facilities, and barbecue grills. This smoke-free guesthouse also has a garden.

Pet friendly

Free WiFi

Guests of Wiseacre enjoy access to free WiFi in public areas, microwave in a common area, and refrigerator in a common area. If you drive, put free parking to good use. Staff members can help with accommodation requests, and provide luggage storage. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Additional amenities include express check-in, a terrace, and laundry facilities.

Pet friendly

Parking included

Don't see what you're looking for?

See all available properties in Chesapeake

View all properties

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.

Hotel Options in Chesapeake

Wingate by Wyndham Chesapeake

817 Greenbrier Circle Chesapeake VA

$85 nightly

$100 total

Apr 26 - Apr 27

Total with taxes and fees

8/10 Very Good! (1,004 reviews)

Holiday Inn Express Chesapeake - Norfolk by IHG

721 Conference Center Drive Chesapeake VA

$107 nightly

$125 total

Apr 19 - Apr 20

Total with taxes and fees

8.6/10 Excellent! (1,000 reviews)

STUDIOS & SUITES 4 LESS CHESAPEAKE

2222 S Military Hwy Chesapeake VA

$64 nightly

$76 total

Apr 20 - Apr 21

Total with taxes and fees

7/10 Good! (767 reviews)

Chesapeake Guest Houses essential information

Accommodation	4 Guest Houses
Lowest Price	$76
Highest Price	$125
Popular accommodation	Country Escape Next DOOR Rental - Sleeps 6 - Stay upstairs in the trees , Steps to Beach \| Studio \| Beach Gear, Pet-Friendly Guesthouse, Walk to Beach, Wiseacre