Choptank River Lighthouse in Cambridge Maryland, on Maryland's Eastern Shore also known as Delmarva.

Cottages in Dorchester County

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Our top choices for Dorchester County cottages

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
9.2 out of 10, Wonderful, (9 reviews)
"The location was perfect. It was quiet and clean with a wonderful view of the water, especially the sunrise through the bedroom window in the morning. The host kept in touch to answer any questions we had, and made sure our stay was great. We will absolutely be back!"
United States
Coulter L.
The price is HK$1,199
HK$2,060 total
includes taxes & fees
15 Jun - 16 Jun
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay
Lusby
10.0 out of 10, Exceptional, (50 reviews)
"Everything was great! Just read the book about the property and amenities…some crucial details about heat and hiking around the neighborhood. Definitely would stay again!"
United States
Chris G.
The price is HK$1,207
HK$2,483 total
includes taxes & fees
17 Jun - 18 Jun
Soul Oasis - home on the 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, (68 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.

Pet-Friendly Smith Island Cottage w/ Golf Cart!

Pet-Friendly Smith Island Cottage w/ Golf Cart!
Ewell
9.8 out of 10, Exceptional, (20 reviews)
"Enjoyed Smith Island , great place to stay, friendly people, loved the golf cart a real plus! Flies and mosquitoes were terrible, restaurant food was just OK! Make sure you get food and supplies before coming! "
United States
richard a. g.
Pet-Friendly Smith Island Cottage w/ Golf Cart!

Rodo Beach Cottage - Dog Friendly Private Beach with Pier - Tesla Charger

Rodo Beach Cottage - Dog Friendly Private Beach with Pier - Tesla Charger
Point Lookout
10.0 out of 10, Exceptional, (20 reviews)
"We loved our stay and are looking forward to going back! I have already recommended it to friends that are looking for a quiet retreat in a great location."
United States
Melissa K.
Rodo Beach Cottage - Dog Friendly Private Beach with Pier - Tesla Charger

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

Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE
Tilghman Island
10.0 out of 10, Exceptional, (14 reviews)
"Everything about the place was perfect for a getaway loved the place everything was handy and setup perfectly to relax and enjoy the scenery "
United States
David M.
Artists, writers & creative minds IMAGINE YOUR GETAWAY AT SIMPLICITY COTTAGE

Updated North Beach Cottage: Pet Friendly!

Updated North Beach Cottage: Pet Friendly!
North Beach
9.6 out of 10, Exceptional, (27 reviews)
"Cozy cottage, beds were comfy and it was great to bring our dog. "
United States
Chloe W.
Updated North Beach Cottage: Pet Friendly!

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, (203 reviews)
"We had a wonderful time and really enjoyed the back screened in porch which is where we spent a lot of time with our two little dogs."
United States
LeaAnne T.
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch

Beachfront Hideaway - Pet Friendly, Hot Tub, EV

Beachfront Hideaway - Pet Friendly, Hot Tub, EV
Lottsburg
9.4 out of 10, Exceptional, (17 reviews)
"The host Brian and Carla were very communicative and very kind throughout our stay. The house itself was gorgeous and every time we had a moment where we thought of something we needed we looked and there it was! The whole house had a really intuitive design. We were very grateful for all of the accommodations."
United States
Veronica B.
Beachfront Hideaway - Pet Friendly, Hot Tub, EV

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

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, (128 reviews)
"Special placeSpecial people"
United States
Phil G.
Waterfront Cottage On Candy Point: Family-Friendly and Dog-Friendly!

Unique Tangier Cottage w/ Chesapeake Bay Views!

Unique Tangier Cottage w/ Chesapeake Bay Views!
Tangier
10.0 out of 10, Exceptional, (15 reviews)
"We enjoyed our time here immensely. The house was beautiful, clean, and well appointed. Our hosts went above and beyond to make our stay enjoyable. We can't wait to return!"
United States
Keri R.
Unique Tangier Cottage w/ Chesapeake Bay Views!

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, (20 reviews)
"The house was very nice and had great amenities supplied by the owners. "
United States
Kenly
Block to Beach! Fossil Hunting, Hot Tub, Coffee Bar, Screened Deck, 1hr to DC

Grace Creek Cottage, Minutes to St. Michaels, Pool, Dock

Grace Creek Cottage, Minutes to St. Michaels, Pool, Dock
Bozman
Grace Creek Cottage, Minutes to St. Michaels, Pool, Dock

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, (67 reviews)
"Our stay was wonderful. The house is very comfortable and immaculate. Everything worked beautifully. The three season screened-in porch and backyard were inspiring with ideas for our own houses. Mark and Karen could easily have a design and landscaping design business; they are also phenomenal hosts! The house is an absolute pleasure! We hope to stay many more times. I highly recommend.. "
United States
Marguerite W.
Accessible, 3 Season Screened-in porch, Sauna, Fire Pit, Dog Friendly

Waterfront Cottage in Beautiful Hoopers Island

Waterfront Cottage in Beautiful Hoopers Island
Fishing Creek
10.0 out of 10, Exceptional, (84 reviews)
"Host was great communicating, place was perfect for a quiet New Year's getaway. Would love to come back in the summer. Thanks for the hospitality."
United States
Curtis C.
Waterfront Cottage in Beautiful Hoopers Island

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, (82 reviews)
"Amazing getaway! Quiet, peaceful, beautiful views. "
United States
Sarah H.
Private Beach Front Getaway at The Sunshine Beach Cottage.

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

Potomac Rvr Woodland Cottage, Polite Pets welcomed, Central Air, Stunning Sunset
Tall Timbers
9.8 out of 10, Exceptional, (61 reviews)
"Lovely house with great hosts. Would stay there again. "
United States
Chad C.
Potomac Rvr Woodland Cottage, Polite Pets welcomed, Central Air, Stunning Sunset

Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.

Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.
Owings
10.0 out of 10, Exceptional, (52 reviews)
"We love this place!"
United States
Joan K.
Relaxing, peaceful house in Calvert County, Md close to beach towns and DC.

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
10.0 out of 10, Exceptional, (1 review)
"Place was perfect"
United States
Scott B.
Spacious 6-bedroom house/cottage in charming Royal Oak with WiFi, AC
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
1,031
Accommodation
185 Cottages
Lowest Price
HK$2,060
Highest Price
HK$2,483

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