Dorchester County Cottages
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Cottages in Dorchester County

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Our top choices for Dorchester County cottages

Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.

2.0 star property

North Beach

9.6 out of 10, Exceptional, (4)

9.6/10

Exceptional

(4)

"Great place in a wonderful area! So cozy & well situated! A perfect weekend getaway!"

Jana S.

The price is HK$1,121

HK$1,121

HK$2,303 total

includes taxes & fees

13 Jan - 14 Jan

Charming 2-bedroom 1 bath cottage with AC, WiFi in peaceful North Beach, Md.

Relaxing Waterfront Cottage Near St Michaels, Maryland

Wittman

9.8 out of 10, Exceptional, (238)

9.8/10

Exceptional

(238)

"We enjoy it very much, we come every year."

bruce j.

Relaxing Waterfront Cottage Near St Michaels, Maryland

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

Downtown St. Michaels

9.6 out of 10, Exceptional, (147)

9.6/10

Exceptional

(147)

"Great location"

Jody M.

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

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

Stevensville

10.0 out of 10, Exceptional, (58)

10/10

Exceptional

(58)

"great stay ! all needs where met . "

randall j.

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

3 bedrooms, desk, iron/ironing board, free WiFi

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

Tall Timbers

9.8 out of 10, Exceptional, (60)

9.8/10

Exceptional

(60)

"We enjoyed our stay! Our Grandkids (2) joined us too. Unfortunately we had to leave early to attend a funeral. We would absolutely consider this property for any future stays in the area. "

Bernadette D.

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

Pet Friendly Delightful Waterfront Cottage on Hoopers Island, MD.

Fishing Creek

10.0 out of 10, Exceptional, (51)

10/10

Exceptional

(51)

"Nice "

Henry

Pet Friendly Delightful Waterfront Cottage on Hoopers Island, MD.

Soul Oasis - home on the Chesapeake Bay

Lusby

9.8 out of 10, Exceptional, (40)

9.8/10

Exceptional

(40)

"Great stay. Teresa was very helpful, the house is fun, and the location is great - nice place to visit."

Samuel W.

The price is HK$973

HK$973

HK$2,113 total

includes taxes & fees

11 Jan - 12 Jan

Soul Oasis - home on the Chesapeake Bay

Beachfront Hideaway - Pet Friendly, Hot Tub, EV

Lottsburg

9.8 out of 10, Exceptional, (13)

9.8/10

Exceptional

(13)

"Most amazing views. Owners are very responsive and made sure we had a wonderful stay. Very family friendly!"

Diane C.

Beachfront Hideaway - Pet Friendly, Hot Tub, EV

John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

Downtown St. Michaels

9.6 out of 10, Exceptional, (125)

9.6/10

Exceptional

(125)

"Ideal location to shops and attractions. Host very easy to reach. "

Don N.

John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!

The Middle Point Cabin in Saint Michaels

Neavitt

9.8 out of 10, Exceptional, (57)

9.8/10

Exceptional

(57)

"We had a great stay. The cottage is just like the pictures. Nice area…lots of things to do."

Michael

The Middle Point Cabin in Saint Michaels

2 Bedroom Cozy Beach Cottage with Water Access

Piney Point

9.6 out of 10, Exceptional, (21)

9.6/10

Exceptional

(21)

"My family and I stayed here a few weeks ago when we were dropping off my niece at St. Mary’s College and we had a wonderful time! The house was clean, had everything we needed, and we loved going by the water and having dinner at the Ruddy Duck (we went two nights in a row)! We’d definitely stay again :)"

Cara R.

2 Bedroom Cozy Beach Cottage with Water Access

Charming Waterfront Cottage Retreat near St. Michaels

Bozman

10.0 out of 10, Exceptional, (10)

10/10

Exceptional

(10)

"My husband and I were delighted to stay in this beautiful home located on the most picturesque property for our 30th wedding anniversary. From the design of the house to the small details within it, making it feel like a home away from home, everything was perfect. We will stay here again should we revisit this area! "

Jennifer F.

Charming Waterfront Cottage Retreat near St. Michaels

Family and Pet-Friendly, Waterfront with Pier

Cambridge

10.0 out of 10, Exceptional, (265)

10/10

Exceptional

(265)

"Robert and Clarissa were welcoming and as hospitable as could be. The scenery was just beautiful. Great stay for Ironman Maryland!"

Karlee C.

Family and Pet-Friendly, Waterfront with Pier

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

Cambridge

10.0 out of 10, Exceptional, (16)

10/10

Exceptional

(16)

"Well equipped and super clean; great place!"

Steve S.

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

Fridge, oven, stovetop, coffee/tea maker

Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi

2.0 star property

Stevensville

10.0 out of 10, Exceptional, (6)

10/10

Exceptional

(6)

"Beautiful home. Very nice and quiet neighborhood on the water. "

shannan t.

The price is HK$3,107

HK$3,107

HK$6,809 total

includes taxes & fees

22 Jan - 23 Jan

Charming 2-bedroom waterfront cottage in peaceful Stevensville with AC, WiFi

Smart TV, fireplace, table football, books

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

Lusby

10.0 out of 10, Exceptional, (55)

10/10

Exceptional

(55)

"Incredible property and stay."

Hunter B.

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

"Dragonfly" Waterfront Cottage on Chesapeake Bay

2.5 star property

Reedville

10.0 out of 10, Exceptional, (3)

10/10

Exceptional

(3)

"Great getaway location right on th4e water. Highly recommended"

James P.

"Dragonfly" Waterfront Cottage on Chesapeake Bay

3 bedrooms, iron/ironing board, travel cot, WiFi

Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK

Churchton

9.8 out of 10, Exceptional, (82)

9.8/10

Exceptional

(82)

"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."

Paul M.

Watrfnt Cottage @ChesapeakeParadise Kayaks/Dogs OK

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

Saint Leonard

10.0 out of 10, Exceptional, (19)

10/10

Exceptional

(19)

"The house was very nice and had great amenities supplied by the owners. "

Kenly

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

Piney Point, private , Beach Front Cottage

Piney Point

10.0 out of 10, Exceptional, (91)

10/10

Exceptional

(91)

"The finest property and hosts that are in the Vrbo company. Absolutely amazing property, stellar hosts and the best experience! "

larry c.

Piney Point, private , Beach Front Cottage

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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