Compare Chesapeake Beach Cottage Rentals

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Featured Cottages in Chesapeake Beach

Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE

Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE

Tilghman Island MD
Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden. Helpful staff is there to provide concierge services, as well as offer insight about the area.
Kitchen
Washer
Beachfront Home Minutes to Downtown Annapolis w Parking & Dog-Friendly

Beachfront Home Minutes to Downtown Annapolis w Parking & Dog-Friendly

Annapolis MD
Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.
Kitchen
Washer
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

St Michaels MD
Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.
Pool
Kitchen
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, barbecue grills, and a garden.
Pool
Kitchen
Accessible, 3 Season Screened-in porch, Sauna, Fire Pit, Dog Friendly

Accessible, 3 Season Screened-in porch, Sauna, Fire Pit, Dog Friendly

Stevensville MD
Guests staying at this cottage enjoy a sauna, laundry facilities, and a garden. This smoke-free cottage also has barbecue grills.
Kitchen
Washer
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town

Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town

St Michaels MD
Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.
Pool
Kitchen
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)

Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)

Cambridge MD
Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.
Kitchen
Washer
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

Saint Michaels MD
Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.
Pool
Kitchen
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
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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
    $162 nightly
    The price is $180 total per night from Oct 4 to Oct 5
    $180 total
    Oct 4 - Oct 5
    Total with taxes and fees
    Sonesta ES Suites Annapolis

    Sonesta ES Suites Annapolis

    170 Admiral Cochrane Dr Edgewater MD
    $91 nightly
    The price is $104 total per night from Sep 24 to Sep 25
    $104 total
    Sep 24 - Sep 25
    Total with taxes and fees
    8.8/10 Excellent! (1,003 reviews)
    St Michaels Inn

    St Michaels Inn

    1228 S Talbot Street St. Michaels MD
    $89 nightly
    The price is $98 total per night from Oct 5 to Oct 6
    $98 total
    Oct 5 - Oct 6
    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
$98
Highest Price
$180
Popular accommodation
 Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE, Beachfront Home Minutes to Downtown Annapolis w Parking & Dog-Friendly, Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels, John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!, Accessible, 3 Season Screened-in porch, Sauna, Fire Pit, Dog Friendly, Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town, Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly), Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch, Family and Pet-Friendly, Waterfront with Pier