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

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Top Cities in Dorchester County

Our top choices for Dorchester County cottages

1. 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
9.0 out of 10, Wonderful, (16 reviews)
"Beautiful view from the house. Extremely clean. Had everything we needed. Can't wait to come back"
United States
ed r.
The price is CA $228
CA $376 total
includes taxes & fees
Nov 12 - Nov 13
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

2. Lovely 2-bedroom waterfront cottage in charming Wittman

Lovely 2-bedroom waterfront cottage in charming Wittman
Wittman
9.8 out of 10, Exceptional, (8 reviews)
"This lovely cottage was just perfect for us! The house is newly updated & located on a beautiful property right on the water. We loved the firepit, seeing all the stars at night & watching the wildlife on the water. The kayaks were a nice surprise too! We visit MD often & will definitely stay here again!"
United States
Beth H.
Lovely 2-bedroom waterfront cottage in charming Wittman

3. 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, (137 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!

4. 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, (132 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!

5. 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, (143 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

6. Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay
Lusby
10.0 out of 10, Exceptional, (68 reviews)
"Nice, clean, and would absolutely stay here again."
United States
Dusty S.
The price is CA $210
CA $422 total
includes taxes & fees
Nov 18 - Nov 19
Soul Oasis - home on the Chesapeake Bay

7. Relaxing Waterfront Cottage Near St Michaels, Maryland

Relaxing Waterfront Cottage Near St Michaels, Maryland
Wittman
9.8 out of 10, Exceptional, (264 reviews)
"We had a great time at a great place."
United States
Jeffrey F.
Relaxing Waterfront Cottage Near St Michaels, Maryland

8. Charming Waterfront Cottage Retreat near St. Michaels

Charming Waterfront Cottage Retreat near St. Michaels
Bozman
10.0 out of 10, Exceptional, (13 reviews)
"This was a great stay for my wife and I on our mini moon. Everything was perfect. The property was well equipped with everything we needed, a great location that was private but not too far from town. We will be back!"
United States
Nick G.
Charming Waterfront Cottage Retreat near St. Michaels

9. 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, (213 reviews)
"Awesome place"
United States
John B.
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

10. 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, (155 reviews)
"Just an over-all fantastic visit/stay!"
United States
James H.
Premier St. Michaels Cottage - T. Blades House - Walk to Everything in Town

11. Walk to Beach: Pet-Friendly Gem in Scotland!

Walk to Beach: Pet-Friendly Gem in Scotland!
Point Lookout
9.0 out of 10, Wonderful, (13 reviews)
"My wife and I loved the access to the semi-private beach, and the quiet area away from the city noise. The property air conditioning was also perfect for a hot weekend in August "
United States
Nate J.
Walk to Beach: Pet-Friendly Gem in Scotland!

12. Family and Pet-Friendly, Waterfront with Pier

Family and Pet-Friendly, Waterfront with Pier
Cambridge
10.0 out of 10, Exceptional, (279 reviews)
"We had a lovely time. The views were amazing. We enjoyed crabbing, kayaking and our genuine conversations with the hosts."
United States
Lisa H.
Family and Pet-Friendly, Waterfront with Pier

13. 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, (28 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

14. 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

15. 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)
"We had a wonderful stay! The house was clean, comfortable, and had everything we needed for a relaxing week. The location is perfect, and we love spending time at the beach with our family. Thank you for sharing your home."
United States
Patricia C.
Private Beach Front Getaway at The Sunshine Beach Cottage.

16. 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)

17. 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, (144 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

18. 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
9.8 out of 10, Exceptional, (9 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

19. Block to Beach! Fossil Hunting, Hot Tub, Coffee Bar, Screened Deck, 1hr to DC

Block to Beach! Fossil Hunting, Hot Tub, Coffee Bar, Screened Deck, 1hr to DC
Saint Leonard
10.0 out of 10, Exceptional, (25 reviews)
"All was great....loved the access to the little private beach with our little ones. Kitchen was clean and orderly and the living room was quaint."
United States
Kristin D.
Block to Beach! Fossil Hunting, Hot Tub, Coffee Bar, Screened Deck, 1hr to DC

20. Renovated, Waterfront, Large Private Deep Water Dock, Cowboy Pool, Fire Pit

Renovated, Waterfront, Large Private Deep Water Dock, Cowboy Pool, Fire Pit
Lusby
10.0 out of 10, Exceptional, (61 reviews)
"Great peaceful location and views within short drive to restaurants. Home was beautifully equipped with everything you could need for cooking in or outdoors. We loved crabbing from the dock and dining with a spectacular sunset."
United States
Laura F.
Renovated, Waterfront, Large Private Deep Water Dock, Cowboy Pool, Fire Pit
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

Find out more about Dorchester County

Dorchester County Cottages information

Number of reviews
1,749
Accommodation
186 Cottages
Lowest Price
CA $376
Highest Price
CA $422

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