Compare Chesapeake Beach 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 Beach

Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

Benedict MD
$241 nightly
The price is $266 total per night
$266 total
Jul 20 - Jul 21
Total with taxes and fees
Guests staying at this cottage have access to barbecue grills and a garden.
Free WiFi
Air conditioning
The Yellow Cottage on Harness Creek

The Yellow Cottage on Harness Creek

Annapolis MD
Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.
Kitchen
Washer
Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA

Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA

Edgewater MD
Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.
Kitchen
Washer
Family and Pet-Friendly, Waterfront with Pier

Family and Pet-Friendly, Waterfront with Pier

Cambridge MD
At this cottage, guests have access to an outdoor pool, laundry facilities, and barbecue grills. This smoke-free cottage also has a garden.
Pool
Kitchen
"Point of View" Waterfront cottage with panoramic views on Tilghman Island

"Point of View" Waterfront cottage with panoramic views on Tilghman Island

Tilghman Island MD
At this cottage, guests have access to features like laundry facilities.
Kitchen
Washer
Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK

Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK

Deale MD
Guests staying at this cottage enjoy a hot tub, laundry facilities, and barbecue grills. This smoke-free cottage also has a garden.
Hot Tub
Kitchen
Cozy Cottage with access to and partially obstructed views of the bay.

Cozy Cottage with access to and partially obstructed views of the bay.

Port Republic MD
Guests staying at this cottage have access to laundry facilities, a garden, and barbecue grills.
Beachfront Home Minutes to Downtown Annapolis Dogs OK

Beachfront Home Minutes to Downtown Annapolis Dogs OK

Annapolis MD
Guests staying at this cottage have access to laundry facilities, a garden, and barbecue grills.
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

Saint Michaels MD
Guests staying at this cottage have access to laundry facilities, a garden, and barbecue grills.
Pool
Kitchen
Don't see what you're looking for?
See all available properties in Chesapeake Beach
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 Beach

    Rod 'N' Reel Resort

    Rod 'N' Reel Resort

    4165 Mears Ave Chesapeake Beach MD
    $210 nightly
    The price is $233 total per night from Jul 29 to Jul 30
    $233 total
    Jul 29 - Jul 30
    Total with taxes and fees
    8.6/10 Excellent! (1,004 reviews)
    St Michaels Inn

    St Michaels Inn

    1228 S Talbot Street St. Michaels MD
    $95 nightly
    The price is $104 total per night from Aug 16 to Aug 17
    $104 total
    Aug 16 - Aug 17
    Total with taxes and fees
    8.2/10 Very Good! (1,009 reviews)
    Spark by Hilton Waldorf

    Spark by Hilton Waldorf

    11770 Business Park Drive Waldorf MD
    $77 nightly
    The price is $86 total per night from Aug 2 to Aug 3
    $86 total
    Aug 2 - Aug 3
    Total with taxes and fees

Cottages

Book a cottage in Chesapeake Beach
Spend your next getaway treating yourself to a quieter, simpler way of life in a private cottage in Chesapeake Beach. 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 Beach better.

Cottage apartments in Chesapeake Beach 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 Beach
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 Beach 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 Beach 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 Beach. 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 Beach Cottages essential information

Accommodation
73 Cottages
Lowest Price
$86
Highest Price
$266
Popular accommodation
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch., The Yellow Cottage on Harness Creek, Charming Waterfront Cottage with Private Dock. Close to Annapolis & USNA, Family and Pet-Friendly, Waterfront with Pier, "Point of View" Waterfront cottage with panoramic views on Tilghman Island, Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK, Cozy Cottage with access to and partially obstructed views of the bay., Beachfront Home Minutes to Downtown Annapolis Dogs OK, John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!