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

Rustic Beach Front Apartment - Cozy, Rustic and On the Beach! - 2 BR/1 Bath

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

Cozy Beach Cottage - Walking distance to the Beach!!

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

$356 nightly

$413 total

Oct 5 - Oct 6

Total with taxes and fees

At this cottage, guests have access to features like laundry facilities. This smoke-free cottage also has barbecue grills.

Steps to the Ocean! Family and Dog Friendly North End Cottage w/ Rsrv Parking

$406 nightly

$469 total

Nov 2 - Nov 3

Total with taxes and fees

At this cottage, guests have access to features like laundry facilities. This smoke-free cottage also has a garden.

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

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

GREAT ADVERTURE BEGINS WHERE THE BLACKTOP ENDS! 6.75 miles! sand, surf & horses!

At this cottage, guests have access to features like laundry facilities. This smoke-free cottage also has barbecue grills.

Waterfront Cottage w/ Dock/Kayaks + Dog Friendly

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.

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

At this cottage, guests have access to features like laundry facilities.

6 Block to oceanfront and in the center of the vibe district!

At this cottage, guests have access to a garden.

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

Comfort Suites Chesapeake - Norfolk

1550 Crossways Blvd Chesapeake VA

$84 nightly

$99 total

Nov 3 - Nov 4

Total with taxes and fees

YourSpace Hotels Chesapeake

2137 Starmount Parkway Chesapeake VA

$94 nightly

$110 total

Oct 19 - Oct 20

Total with taxes and fees

9.6/10 Exceptional! (236 reviews)

Surfbreak Virginia Beach Oceanfront, an Ascend Collection Hotel

1101 Atlantic Ave Virginia Beach VA

$80 nightly

$94 total

Oct 18 - Oct 19

Total with taxes and fees

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	141 Cottages
Lowest Price	$94
Highest Price	$469
Popular accommodation	Rustic Beach Front Apartment - Cozy, Rustic and On the Beach! - 2 BR/1 Bath, Cozy Beach Cottage - Walking distance to the Beach!!, Norfolk Beach Cottage Rental, Steps to the Ocean! Family and Dog Friendly North End Cottage w/ Rsrv Parking, Mermaid's and Mutts Retreat - Beach Front, Pet Friendly, Wi-Fi, Off-Street Park, GREAT ADVERTURE BEGINS WHERE THE BLACKTOP ENDS! 6.75 miles! sand, surf & horses!, Waterfront Cottage w/ Dock/Kayaks + Dog Friendly, Adorable Chesapeake Bay Beach Cottage A Just 1 Block from the Sand!, 6 Block to oceanfront and in the center of the vibe district!