Cottages in Dorchester County

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Our top choices for Dorchester County cottages

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, (200 reviews)
"Perfect house close to St Michael’s attractions"
United States
Carolyn E.
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

"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, (15 reviews)
"Amazing property well presented with fantastic views in all directions"
United Kingdom
David G.
"Point of View" Waterfront cottage with panoramic views on Tilghman Island

Hideaway in Hays Beach: 1 Minute Walk to Western Sandy Shore of Chesapeake Bay

Hideaway in Hays Beach: 1 Minute Walk to Western Sandy Shore of Chesapeake Bay
Point Lookout
10.0 out of 10, Exceptional, (127 reviews)
"Hideaway at Hayes Beach was amazing It was a wonderful place to spend Christmas with our family. We were lucky enough to get snow! My husband and I enjoy walking so it was a prefect place to for it. Would definitely recommend this place"
United States
April T.
The price is HK$1,959
HK$4,196 total
includes taxes & fees
3 May - 4 May
Hideaway in Hays Beach: 1 Minute Walk to Western Sandy Shore of Chesapeake Bay

Family and Pet-Friendly, Waterfront with Pier

Family and Pet-Friendly, Waterfront with Pier
Cambridge
10.0 out of 10, Exceptional, (265 reviews)
"The hosts were very welcoming, helpful, good communication throughout the reservation process and stay."
United States
Ann R.
Family and Pet-Friendly, Waterfront with Pier

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, (63 reviews)
"great stay ! all needs where met . "
United States
randall j.
Accessible, 3 Season Screened-in porch, Sauna, Fire Pit, Dog Friendly

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, (126 reviews)
"Ideal location to shops and attractions. Host very easy to reach. "
United States
Don N.
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

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, (55 reviews)
"Incredible property and stay."
United States
Hunter B.
Renovated, Waterfront, Large Private Deep Water Dock, Cowboy Pool, Fire Pit

2 Bedroom Cozy Beach Cottage with Water Access

2 Bedroom Cozy Beach Cottage with Water Access
Piney Point
9.6 out of 10, Exceptional, (22 reviews)
"Great place to stay"
United States
Sean H.
2 Bedroom Cozy Beach Cottage with Water Access

Relaxing Waterfront Cottage Near St Michaels, Maryland

Relaxing Waterfront Cottage Near St Michaels, Maryland
Wittman
9.8 out of 10, Exceptional, (241 reviews)
"A cozy cottage, definitely met our needs. Beautiful view!"
United States
Cynthia Louise C.
Relaxing Waterfront Cottage Near St Michaels, Maryland

Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay
Lusby
10.0 out of 10, Exceptional, (43 reviews)
"House was very nice and tidy and exactly as described. The host had a small binder full of helpful info including local restaurants and attractions. There was so much to do and everything was close bye. "
United States
Mindy V.
The price is HK$987
HK$2,210 total
includes taxes & fees
13 Apr - 14 Apr
Soul Oasis - home on the Chesapeake Bay

Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland

Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland
Point Lookout
9.4 out of 10, Exceptional, (12 reviews)
"Pet friendly, easy check out, no cleaning involved."
United States
Naomi B.
The price is HK$1,842
HK$3,513 total
includes taxes & fees
9 Apr - 10 Apr
Cozy Sunrise Waterfront 2-bedroom Cottage & Dock. Serene Point Lookout/Scotland

Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK

Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK
Deale
9.8 out of 10, Exceptional, (83 reviews)
"The cottage was a wonderful place for me and my kids to stay. I really appreciate the thoughtfulness of the owner. We would definitely stay here again."
United States
Paul M.
Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK

Charming Intown Cottage – The Ultimate Walkable Getaway steps from Downtown!

Charming Intown Cottage – The Ultimate Walkable Getaway steps from Downtown!
Downtown St. Michaels
9.8 out of 10, Exceptional, (59 reviews)
"It's a very nice place and the location is great. Its not a professionally managed house which is fine, but we didn't know that going in. Everything is clean, but not professionally clean i.e. the sheets are clean but the mattress pad was not. I would stay there again."
United States
Casey G.
Charming Intown Cottage – The Ultimate Walkable Getaway steps from Downtown!

BEACH COTTAGE BY THE SEA....

BEACH COTTAGE BY THE SEA....
Reedville
10.0 out of 10, Exceptional, (32 reviews)
"The house is small, but works great for a getaway and has everything you need. We spent most of our time at the beach or on the deck -- so peaceful! "
United States
Robin B.
BEACH COTTAGE BY THE SEA....

"Dragonfly" Waterfront Cottage on Chesapeake Bay

"Dragonfly" Waterfront Cottage on Chesapeake Bay
Reedville
10.0 out of 10, Exceptional, (3 reviews)
"Great getaway location right on th4e water. Highly recommended"
United States
James P.
"Dragonfly" Waterfront Cottage on Chesapeake Bay

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, (64 reviews)
"Wonderful property stocked full of anything you would need for a great vacation. We had a great time! Thank you!"
United States
Cody G.
Relax & Renew in a WATERFRONT Cottage , private pier, kayaks, fishing, wineries.

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, (125 reviews)
"Perfect place for a quiet getaway at the beach!"
United States
Cheryl S.
𝑩𝑨𝒀 𝑺𝑰𝑫𝑬 𝑹𝑬𝑻𝑹𝑬𝑨𝑻, ON THE SANDS OF THE 𝐂𝐇𝐄𝐒𝐀𝐏𝐄𝐀𝐊𝐄 𝐁𝐀𝐘

Spacious 6-bedroom house/cottage in charming Royal Oak with WiFi, AC

Spacious 6-bedroom house/cottage in charming Royal Oak with WiFi, AC
Royal Oak
Spacious 6-bedroom house/cottage in charming Royal Oak with WiFi, AC

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
9.4 out of 10, Exceptional, (130 reviews)
"Our dog was so comfortable and welcome at this rental!"
United States
Kathie F.
Location, Location, Location! - W Melson House - Beautiful - In Town St Michaels

Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.

Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.
West River
9.8 out of 10, Exceptional, (43 reviews)
"This was such a beautiful property right on the water! It was everything I wanted for a quiet weekend away. The host was quick to respond and full of great recommendations. I am definitely planning on staying here again and will recommend it to anyone else 10/10"
United States
Meghan G.
Serene spot, West River dock, sunsets, the Bay, only 40 min from Alexandria, DC.
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
1,653
Accommodation
179 Cottages
Lowest Price
HK$2,210
Highest Price
HK$4,196

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