Book Dorchester County, MD Cottages

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Top cities with Cottages to explore in Dorchester County

Cambridge

Cottages

Top Cottages in Dorchester County

Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.

North Beach MD

$260 nightly

$276 total

Jan 1 - Jan 2, 2026

Total with taxes and fees

This cottage featured laundry facilities and barbecue grills.

Washer

Dryer

Relaxing Waterfront Cottage Near St Michaels, Maryland

Wittman MD

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An outdoor pool is featured at this cottage, along with a garden and laundry facilities. Barbecue grills are provided for your convenience.

Pool

Kitchen

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

St Michaels MD

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This cottage features a garden, laundry facilities, and barbecue grills.

Pool

Kitchen

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

Stevensville MD

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A sauna is featured at this cottage, along with a garden and laundry facilities. Barbecue grills are provided for your convenience.

Kitchen

Washer

Potomac Rvr Woodland Cottage, Polite Pets welcomed, Central Air, Stunning Sunset

Tall Timbers MD

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This cottage features a garden, laundry facilities, and barbecue grills. There's fun for all ages with a playground and an arcade/game room.

Kitchen

Washer

Pet Friendly Delightful Waterfront Cottage on Hoopers Island, MD.

Fishing Creek MD

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This cottage includes a garden and barbecue grills.

Kitchen

Pet friendly

Soul Oasis - home on the Chesapeake Bay

Lusby MD

$265 nightly

$281 total

Dec 22 - Dec 23

Total with taxes and fees

This cottage featured laundry facilities and barbecue grills.

Kitchen

Washer

Beachfront Hideaway - Pet Friendly, Hot Tub, EV

Lottsburg VA

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A hot tub is featured at this cottage, along with a garden and laundry facilities. Barbecue grills are provided for your convenience.

Hot Tub

Kitchen

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

Saint Michaels MD

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This cottage features a garden, laundry facilities, and barbecue grills.

Pool

Kitchen

The Middle Point Cabin in Saint Michaels

Neavitt MD

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This cottage features a garden, laundry facilities, and barbecue grills.

Kitchen

Washer

2 Bedroom Cozy Beach Cottage with Water Access

Piney Point MD

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This cottage featured laundry facilities and barbecue grills.

Kitchen

Washer

Charming Waterfront Cottage Retreat near St. Michaels

Bozman MD

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This cottage includes a garden and laundry facilities.

Kitchen

Washer

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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.

Dorchester County Cottages essential information

Accommodation	179 Cottages
Lowest Price	$276
Highest Price	$281
Popular accommodation	Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md., Relaxing Waterfront Cottage Near St Michaels, Maryland, Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town, Accessible, Screened-in porch, Sauna, Fire Pit, Dog Friendly, Potomac Rvr Woodland Cottage, Polite Pets welcomed, Central Air, Stunning Sunset, Pet Friendly Delightful Waterfront Cottage on Hoopers Island, MD., Soul Oasis - home on the Chesapeake Bay, Beachfront Hideaway - Pet Friendly, Hot Tub, EV, John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!, The Middle Point Cabin in Saint Michaels, 2 Bedroom Cozy Beach Cottage with Water Access, Charming Waterfront Cottage Retreat near St. Michaels