Compare Chesapeake Cottage 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 Cottages in Chesapeake

Comfortable & Private 2 Bedrm Cottage w/ King bed.

Comfortable & Private 2 Bedrm Cottage w/ King bed.

Portsmouth VA
$290 nightly
The price is $337 total per night
$337 total
Jun 14 - Jun 15
Total with taxes and fees
At this cottage, guests have access to features like laundry facilities.
Kitchen
Washer
Sandy Dunes BeachFront Cottage - Beach Front

Sandy Dunes BeachFront Cottage - Beach Front

Norfolk VA
Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.
Kitchen
Washer
Waterfront Cottage w/ Dock/Kayaks + Dog Friendly

Waterfront Cottage w/ Dock/Kayaks + Dog Friendly

Virginia Beach VA
Guests staying at this cottage enjoy access to a water park, a gym, and a sauna. Other amenities at this beach cottage include laundry facilities and barbecue grills.
Pool
Kitchen
6.75 miles past, where the blacktop ends! A great adventure awaits!

6.75 miles past, where the blacktop ends! A great adventure awaits!

Corolla NC
At this cottage, guests have access to features like laundry facilities. This smoke-free cottage also has barbecue grills.
Kitchen
Washer
Carova Beach Canal Front Cottage 4x4 required Beach Parking Pass provided

Carova Beach Canal Front Cottage 4x4 required Beach Parking Pass provided

Corolla NC
At this cottage, guests have access to features like laundry facilities. This smoke-free cottage also has barbecue grills.
Kitchen
Washer
Norfolk Beach Cottage Rental

Norfolk Beach Cottage Rental

Norfolk VA
At this cottage, guests have access to features like laundry facilities. This smoke-free cottage also has barbecue grills.
Kitchen
Washer
Adorable Chesapeake Bay Beach Cottage A Just 1 Block from the Sand!

Adorable Chesapeake Bay Beach Cottage A Just 1 Block from the Sand!

Virginia Beach VA
At this cottage, guests have access to features like laundry facilities and local meal delivery service.
Kitchen
Washer
Waterview Cabin on Currituck Sound - Great Campground Amenities (WV90)

Waterview Cabin on Currituck Sound - Great Campground Amenities (WV90)

Coinjock NC
This cottage is a smoke-free cottage.
Free WiFi
Air conditioning
Mermaid's and Mutts Retreat - Beach Front, Pet Friendly, Wi-Fi, Off-Street Park

Mermaid's and Mutts Retreat - Beach Front, Pet Friendly, Wi-Fi, Off-Street Park

Norfolk VA
Guests staying at this cottage have access to laundry facilities, a garden, and barbecue grills.
Kitchen
Washer
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

    Wingate by Wyndham Chesapeake

    817 Greenbrier Circle Chesapeake VA
    $110 nightly
    The price is $128 total per night from Jul 5 to Jul 6
    $128 total
    Jul 5 - Jul 6
    Total with taxes and fees
    7.8/10 Good! (1,075 reviews)
    Comfort Suites Chesapeake - Norfolk

    Comfort Suites Chesapeake - Norfolk

    1550 Crossways Blvd Chesapeake VA
    $128 nightly
    The price is $150 total per night from Jun 14 to Jun 15
    $150 total
    Jun 14 - Jun 15
    Total with taxes and fees
    8.8/10 Excellent! (1,024 reviews)
    STUDIOS & SUITES 4 LESS CHESAPEAKE

    STUDIOS & SUITES 4 LESS CHESAPEAKE

    2222 S Military Hwy Chesapeake VA
    $70 nightly
    The price is $83 total per night from Jun 14 to Jun 15
    $83 total
    Jun 14 - Jun 15
    Total with taxes and fees
    7/10 Good! (831 reviews)

Cottages

Book a cottage in Chesapeake
Spend your next getaway treating yourself to a quieter, simpler way of life in a private cottage in Chesapeake. Cozy and charming, cottage rentals are the ideal spot when you want the comforts of home paired with a one-of-a-kind experience. They’re perfect for a single traveler looking for peace and quiet, or small groups who want to get to know Chesapeake better.

Cottage apartments in Chesapeake range from rustic to luxurious, with just about everything in between. Orbitz gives you the best deals on all of them.

Find the best cottages in Chesapeake
City cottages are great if you want a cozy, comfy place to stay without being far from the all the cool spots you want to check out. A cottage makes a great home base for a day filled with adventure in Chesapeake and the surrounding area. Not willing to give up all the comforts of a fine hotel? A luxury cottage turns up the charm while offering perks like room service, cable television, sunken spa tubs and housekeeping.

Stay in a Chesapeake cottage and swap busy days for peaceful evenings. Use the kitchenette or full kitchen to come up with a meal or reheat leftovers from your afternoon in Chesapeake. You may even be able to use a pool and laundry facilities. Whether you’re in the mood for quiet relaxation or a night on the town, a cottage puts you right where you want to be.

Chesapeake Cottages essential information

Accommodation
161 Cottages
Lowest Price
$83
Highest Price
$337
Popular accommodation
Comfortable & Private 2 Bedrm Cottage w/ King bed., Sandy Dunes BeachFront Cottage - Beach Front, Waterfront Cottage w/ Dock/Kayaks + Dog Friendly, 6.75 miles past, where the blacktop ends! A great adventure awaits!, Carova Beach Canal Front Cottage 4x4 required Beach Parking Pass provided, Norfolk Beach Cottage Rental, Adorable Chesapeake Bay Beach Cottage A Just 1 Block from the Sand!, Waterview Cabin on Currituck Sound - Great Campground Amenities (WV90), Mermaid's and Mutts Retreat - Beach Front, Pet Friendly, Wi-Fi, Off-Street Park

More to Explore