A lighthouse on a pier with a red roof and white walls, surrounded by calm water.

Cottages in Dorchester County

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Dorchester County cottages

A white colonial-style house with a brick chimney, a wooden picket fence, and a brick pathway leading to the entrance.

1. 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!
Downtown St. Michaels
9.6 out of 10, Exceptional, (135 reviews)
"A beautiful, historic home perfectly situated in the heart of St. Michael’s."
United States
Laura C.
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
A two-story house with a front porch, a small attached garage, and a picket fence.

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

Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
Downtown St. Michaels
9.6 out of 10, Exceptional, (142 reviews)
"Great location in St Michaels at a fun historical house."
United States
Adam
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels
A white house with a red door and chimney, surrounded by greenery and a view of the water.

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

Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE
Tilghman Island
9.8 out of 10, Exceptional, (27 reviews)
"The place is exactly as you see gorgeous views, if you’re looking for a place to rest this is the place. It’s not a fancy place but it’s cozy and you will find all that you need and it’s very clean ."
United States
Rita
Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE
A two-story house with a brick roof, a front door, and a picket fence.

4. 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
Downtown St. Michaels
9.8 out of 10, Exceptional, (212 reviews)
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
A wooden deck leading to a beach with a sunset in the background.

5. BEACH COTTAGE BY THE SEA....

BEACH COTTAGE BY THE SEA....
Reedville
9.8 out of 10, Exceptional, (41 reviews)
"Very nice place to enjoy a a beach view. The atmosphere is very great!"
United States
Daniel F.
BEACH COTTAGE BY THE SEA....
A wooden deck with two white Adirondack chairs and a table, overlooking a calm body of water during sunset.

6. Relax & Renew in a WATERFRONT Cottage , private pier, kayaks, fishing, wineries.

Relax & Renew in a WATERFRONT Cottage , private pier, kayaks, fishing, wineries.
Lottsburg
10.0 out of 10, Exceptional, (76 reviews)
"Host was great! Very much accommodating. The view was amazing and so much for families to do!"
United States
Alysia L.
Relax & Renew in a WATERFRONT Cottage , private pier, kayaks, fishing, wineries.
A wooden deck with two green metal chairs and a table, overlooking a body of water.

7. Waterfront Cottage On Candy Point: Family-Friendly and Dog-Friendly!

Waterfront Cottage On Candy Point: Family-Friendly and Dog-Friendly!
Heathsville
9.6 out of 10, Exceptional, (131 reviews)
"Amazing location. Perfect host. Very quiet location. Special place to visit and relax. Hope to come back again!"
United States
Robin F.
Waterfront Cottage On Candy Point: Family-Friendly and Dog-Friendly!
A snow-covered wooden cabin with a porch, surrounded by trees and a body of water.

8. Family and Pet-Friendly, Waterfront with Pier

Family and Pet-Friendly, Waterfront with Pier
Cambridge
10.0 out of 10, Exceptional, (278 reviews)
"Rob was such a wonderful and inviting host"
United States
Stacy S.
Family and Pet-Friendly, Waterfront with Pier
A triangular cabin with a wooden staircase leading to a door, surrounded by trees.

9. Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay
Lusby
10.0 out of 10, Exceptional, (66 reviews)
"Nice, clean, and would absolutely stay here again."
United States
Dusty S.
Soul Oasis - home on the Chesapeake Bay
A waterfront property with a white building featuring multiple windows and balconies, surrounded by trees and reflecting a light source on the water.

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

"Point of View" Waterfront cottage with panoramic views on Tilghman Island
Tilghman Island
10.0 out of 10, Exceptional, (35 reviews)
"Our stay at Point of View cottage was wonderful! Everything was exactly as described. Communication with Maria was excellent and her recommendations were spot on! We will definitely stay there again!"
United States
Pam S.
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
A white lighthouse with a black top, a white building with black shutters, and a staircase leading to the entrance.

11. Potomac River Woodland Cottage, Polite Pets welcome Central Air Stunning Sunset

Potomac River Woodland Cottage, Polite Pets welcome Central Air Stunning Sunset
Tall Timbers
9.8 out of 10, Exceptional, (67 reviews)
"Great location, house was clean and well furnished. Hosts were very accommodating. Would definitely stay here again."
United States
Terence B.
Potomac River Woodland Cottage, Polite Pets welcome Central Air Stunning Sunset
A white wooden house with a gabled roof, a front porch, and a small flag.

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

Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
Downtown St. Michaels
9.6 out of 10, Exceptional, (153 reviews)
"Great house in town well furnished "
United States
Donna M.
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town
A hot tub in a backyard with a view of a lake and trees.

13. Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK

Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK
Deale
9.8 out of 10, Exceptional, (91 reviews)
Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK
A wooden deck with a table and chairs, a large umbrella, and a view of a tree and open field.

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

Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Cambridge
10.0 out of 10, Exceptional, (19 reviews)
"We had a wonderful stay, very quiet and peaceful. Views from the pier were amazing!"
United States
Reviews B.
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
A modern house with a dark roof, large windows, and a front porch with chairs.

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

Accessible, 3 Season Screened-in porch, Sauna, Fire Pit, Dog Friendly
Stevensville
10.0 out of 10, Exceptional, (74 reviews)
"An amazing house! Wonderful hosts who were very responsive and paid attention to every detail. Would definitely stay again! "
United States
maria T.
Accessible, 3 Season Screened-in porch, Sauna, Fire Pit, Dog Friendly
A wooden deck with chairs and tables overlooking the ocean at sunset.

16. 𝑩𝑨𝒀 𝑺𝑰𝑫𝑬 𝑹𝑬𝑻𝑹𝑬𝑨𝑻, ON THE SANDS OF THE 𝐂𝐇𝐄𝐒𝐀𝐏𝐄𝐀𝐊𝐄 𝐁𝐀𝐘

𝑩𝑨𝒀 𝑺𝑰𝑫𝑬 𝑹𝑬𝑻𝑹𝑬𝑨𝑻, ON THE SANDS OF THE 𝐂𝐇𝐄𝐒𝐀𝐏𝐄𝐀𝐊𝐄 𝐁𝐀𝐘
Point Lookout
10.0 out of 10, Exceptional, (141 reviews)
"Place is a gem. Great views, beautiful beach, very relaxing. Cant wait to come back. "
United States
Scott S.
𝑩𝑨𝒀 𝑺𝑰𝑫𝑬 𝑹𝑬𝑻𝑹𝑬𝑨𝑻, ON THE SANDS OF THE 𝐂𝐇𝐄𝐒𝐀𝐏𝐄𝐀𝐊𝐄 𝐁𝐀𝐘
A small, single-story house with a porch, a small attached garage, and a fenced yard.

17. Private Beach Front Getaway at The Sunshine Beach Cottage.

Private Beach Front Getaway at The Sunshine Beach Cottage.
Point Lookout
9.8 out of 10, Exceptional, (87 reviews)
"Location is fantastic! Adorable cottage with all the basics. Best part was kayaking right out the front door and crabbing at the nearby creek."
United States
Lisa R.
Private Beach Front Getaway at The Sunshine Beach Cottage.
A covered patio with a round table and chairs, overlooking a body of water with a dock in the background.

18. Waterfront Cottage in Mt. Vernon

Waterfront Cottage in Mt. Vernon
Princess Anne
10.0 out of 10, Exceptional, (2 reviews)
"Cute Cottage, great view."
United States
Matthew B.
Waterfront Cottage in Mt. Vernon
A modern living room with a grey sofa, a coffee table, and a TV mounted on the wall. A kitchen is visible in the background with wooden cabinets and a window.

19. Beautiful Waterfront 2-bedroom cottage in tranquil Piney Point with WiFi, AC

Beautiful Waterfront 2-bedroom cottage in tranquil Piney Point with WiFi, AC
Piney Point
10.0 out of 10, Exceptional, (8 reviews)
"We had a great time! The cottage was perfect for our needs and clean. We loved spending time in the water on the paddle boat. "
United States
Samantha D.
Beautiful Waterfront 2-bedroom cottage in tranquil Piney Point with WiFi, AC
A two-story house with a red-roofed deck, a swimming pool, and a garden with various plants.

20. Pool - Hot Tub - Rec Room - Private Dock: Year Round Playground

Pool - Hot Tub - Rec Room - Private Dock: Year Round Playground
Marion Station
Pool - Hot Tub - Rec Room - Private Dock: Year Round Playground
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.
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Top Dorchester County Hotel Reviews

St Michaels Inn

St Michaels Inn

10/10 Excellent
"It was extremely helpful to my mobility challenged companion to have a parking space right in front of the room. The lobby area was charming, comfortable with fresh coffee, particularly helpful when we had to wait for a tow truck driver for our disabled car. The staff member Alison provided help in a variety of ways, local auto shop, contact with a driver, fresh coffee, etc."
Mary 1-night trip
Posted 17 hours ago
St Michaels Inn

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