Cottages in Dorchester County

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Check prices for these dates

In two weeks
1 May - 3 May
In two months
12 Jun - 14 Jun
In three months
10 Jul - 12 Jul
In four months
7 Aug - 9 Aug

Our top choices for Dorchester County cottages

Exterior

Luxe Chesapeake Bay Getaway < 20 Mi to Annapolis!

Luxe Chesapeake Bay Getaway < 20 Mi to Annapolis!
3.0 star property
Shady Side
Luxe Chesapeake Bay Getaway < 20 Mi to Annapolis!
House (3 Bedrooms) | Front of property

6 Mi to Salisbury: Forest-view Sanctuary!

6 Mi to Salisbury: Forest-view Sanctuary!
3.0 star property
Parsonsburg
The price is 2.739.152 ₫
7.127.590 ₫ total
includes taxes & fees
4 May - 5 May
6 Mi to Salisbury: Forest-view Sanctuary!
Cottage (2 Bedrooms) | Interior

Adorable Beach Cottage w/ Hot Tub & Tropical Bar!

Adorable Beach Cottage w/ Hot Tub & Tropical Bar!
3.0 star property
Chesapeake Beach
8.0 out of 10, Very good, (2 reviews)
"It really is an adorable cottage, very tastefully decorated.the owner provided a very thoughtful gift basket on arrival. I would recommend this cottage to anyone."
United States
Anne
Adorable Beach Cottage w/ Hot Tub & Tropical Bar!
House (2 Bedrooms) | Front of property

Tilghman Island Retreat By Knapps Narrows!

Tilghman Island Retreat By Knapps Narrows!
3.0 star property
Tilghman
Tilghman Island Retreat By Knapps Narrows!
House (3 Bedrooms) | Interior

Getaway on 1/2 Acre w/ Deck in Georgetown

Getaway on 1/2 Acre w/ Deck in Georgetown
3.0 star property
Georgetown
10.0 out of 10, Exceptional, (1 review)
"This place is just as you see in the photos; clean, welcoming, great location, and very peaceful. We are certainly looking forward to staying here next year, if available. The contact person was available and answered quickly when I contacted him. "
United States
ANA
Getaway on 1/2 Acre w/ Deck in Georgetown
House (3 Bedrooms) | Front of property

Bayfront Maryland Retreat w/ Deck, Near Beaches!

Bayfront Maryland Retreat w/ Deck, Near Beaches!
3.0 star property
North Beach
Bayfront Maryland Retreat w/ Deck, Near Beaches!
Cottage (2 Bedrooms) | Interior

Pet-friendly Smith Island Cottage w/ Golf Cart!

Pet-friendly Smith Island Cottage w/ Golf Cart!
3.0 star property
Smith Island
10.0 out of 10, Exceptional, (1 review)
"We had a lovely 2 night stay. The owners and host were wonderful. We were so happy to have use of the golf cart and bicycles. The cottage is adorable with beautiful touches all around."
United States
Karl
Pet-friendly Smith Island Cottage w/ Golf Cart!
Cottage (4 Bedrooms) | Interior

Unique Tangier Cottage w/ Chesapeake Bay Views!

Unique Tangier Cottage w/ Chesapeake Bay Views!
3.0 star property
Tangier
Unique Tangier Cottage w/ Chesapeake Bay Views!
Cottage (3 Bedrooms) | Front of property

Updated North Beach Cottage: Pet Friendly!

Updated North Beach Cottage: Pet Friendly!
3.0 star property
North Beach
6.0 out of 10, (1 review)
"The property needs a severe cleaning. The floors were filthy. "
United States
Lacy
Updated North Beach Cottage: Pet Friendly!
House (2 Bedrooms) | Interior

Waterfront North Beach Home ~ 2 Mi to Beach!

Waterfront North Beach Home ~ 2 Mi to Beach!
3.0 star property
North Beach
Waterfront North Beach Home ~ 2 Mi to Beach!
House (2 Bedrooms) | Front of property

Walk to Beach: Charming Maryland Home w/ Yard!

Walk to Beach: Charming Maryland Home w/ Yard!
3.0 star property
St. Leonard
10.0 out of 10, Exceptional, (1 review)
"This little gem of a house was absolutely perfect! The house was so close to the beach and to all the places we needed to go. We were visiting from Indiana to attend my son and his wife’s baby shower! The hosts had little snacks, coffee, beach towels, etc at the ready. Everything was so clean and comfortable! Definitely give this place a 10/10! "
United States
Tiffany
Walk to Beach: Charming Maryland Home w/ Yard!
House (4 Bedrooms) | Interior

Beautiful Colonial Home on the Choptank River

Beautiful Colonial Home on the Choptank River
3.0 star property
Cambridge
Beautiful Colonial Home on the Choptank River
House (3 Bedrooms) | Interior

Waterfront Reedville Home w/ Private Dock!

Waterfront Reedville Home w/ Private Dock!
3.0 star property
Reedville
9.0 out of 10, Wonderful, (2 reviews)
"A Wonderful Place and a Wonderful Time! Lots of space to run and play! Nice Kitchen and Dining Area, Lovely Large Screened Porch w/ attached Deck, Lovely Dock and Fire pit etc...Lovely view of the Little Wicomico! Clean and comfortable! Great Stay!!"
United States
Carol
Waterfront Reedville Home w/ Private Dock!
House (3 Bedrooms) | Interior

Walkable Beach Retreat on Chesapeake Bay!

Walkable Beach Retreat on Chesapeake Bay!
3.0 star property
Tangier
Walkable Beach Retreat on Chesapeake Bay!
House (4 Bedrooms) | Interior

Bayfront Gem w/ Amazing Water Views + Pond!

Bayfront Gem w/ Amazing Water Views + Pond!
3.0 star property
Madison
Bayfront Gem w/ Amazing Water Views + Pond!
House (4 Bedrooms) | Interior

Waterfront Cambridge Home: Pool & Dock!

Waterfront Cambridge Home: Pool & Dock!
3.0 star property
Cambridge
Waterfront Cambridge Home: Pool & Dock!
House (4 Bedrooms) | Front of property

Waterfront Retreat < 4 Mi to Dtwn Cambridge!

Waterfront Retreat < 4 Mi to Dtwn Cambridge!
3.0 star property
Cambridge
Waterfront Retreat < 4 Mi to Dtwn Cambridge!
House (4 Bedrooms) | Interior

Spacious Trappe Getaway w/ Outdoor Pool & Gazebo!

Spacious Trappe Getaway w/ Outdoor Pool & Gazebo!
3.0 star property
Trappe
Spacious Trappe Getaway w/ Outdoor Pool & Gazebo!
House (5 Bedrooms) | Front of property

Riverside House w/ Kayaks, Piano & Fireplace

Riverside House w/ Kayaks, Piano & Fireplace
3.0 star property
California
Riverside House w/ Kayaks, Piano & Fireplace
House (4 Bedrooms) | Interior

Maryland Retreat: Walk to Bay, Beach & Boat Ramp!

Maryland Retreat: Walk to Bay, Beach & Boat Ramp!
3.0 star property
Deal Island
10.0 out of 10, Exceptional, (2 reviews)
"Osprey House was the perfect location for our getaway! The owners were amazing and the house was gorgeous! The view from the back yard was exactly what we needed after a long day at a wrestling tournament! "
United States
Jessica
Maryland Retreat: Walk to Bay, Beach & Boat Ramp!
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

Holiday Inn Express Cambridge by IHG

Holiday Inn Express Cambridge by IHG

8/10 Good
"Room was impeccable, staff professional and courteous, room somewhat noisy due to being right off Ocean Gateway. Overall it was a good stay."
Philippe 3-night trip
Posted 4 hours ago
Holiday Inn Express Cambridge by IHG

Find out more about Dorchester County

Dorchester County Cottages information

Number of reviews
10
Accommodation
104 Cottages
Lowest Price
7.127.590 ₫
Highest Price
7.127.590 ₫