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

Cottages in Dorchester County

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Check prices for these dates

In two weeks
11 Sep - 13 Sep
In two months
23 Oct - 25 Oct
In three months
20 Nov - 22 Nov
In four months
18 Dec - 20 Dec

Our top choices for Dorchester County cottages

Property grounds

1. 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, (72 reviews)
"Host was great! Very much accommodating. The view was amazing and so much for families to do!"
United States
Alysia L.
Relax & Renew in a WATERFRONT Cottage , private pier, kayaks, fishing, wineries.
Terrace/patio

2. Private sand beach on Chesapeake Bay--Great for Kids--Sunrise/Sunset Views

Private sand beach on Chesapeake Bay--Great for Kids--Sunrise/Sunset Views
Heathsville
10.0 out of 10, Exceptional, (35 reviews)
"Lovely location. Very quiet. Well equipped."
United States
Anonymous traveler
Private sand beach on Chesapeake Bay--Great for Kids--Sunrise/Sunset Views
Exterior

3. 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, (138 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
Exterior

4. "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, (27 reviews)
"The views are an amazing. The cottage is well appointed. The hosts were responsive. It was an excellent trip"
United States
Paul H.
"Point of View" Waterfront cottage with panoramic views on Tilghman Island
Terrace/patio

5. Waterfront Maryland Retreat w/ Dock & Bay View!

Waterfront Maryland Retreat w/ Dock & Bay View!
Deal Island Historic District
9.4 out of 10, Exceptional, (11 reviews)
"IF a Quiet, Peaceful, Beautiful place to stay is what your looking for this is the place for you."
United States
Jerry Walberg
Waterfront Maryland Retreat w/ Dock & Bay View!
Exterior

6. Pet Friendly Delightful Waterfront Cottage on Hoopers Island, MD.

Pet Friendly Delightful Waterfront Cottage on Hoopers Island, MD.
Fishing Creek
10.0 out of 10, Exceptional, (52 reviews)
"Nice "
United States
Henry
Pet Friendly Delightful Waterfront Cottage on Hoopers Island, MD.
Exterior

7. Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay
Lusby
10.0 out of 10, Exceptional, (58 reviews)
"Nice, clean, and would absolutely stay here again."
United States
Dusty S.
The price is AED 577
AED 1,187 total
includes taxes & fees
15 Sep - 16 Sep
Soul Oasis - home on the Chesapeake Bay
Exterior

8. 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, (208 reviews)
"Awesome place"
United States
John B.
Carpenter St. Cottage In the Heart of St Michaels Village - Large Screened Porch
Exterior

9. 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, (85 reviews)
"Amazing getaway! Quiet, peaceful, beautiful views. "
United States
Sarah H.
Private Beach Front Getaway at The Sunshine Beach Cottage.
Property grounds

10. BEACH COTTAGE BY THE SEA....

BEACH COTTAGE BY THE SEA....
Reedville
9.8 out of 10, Exceptional, (39 reviews)
"Great peaceful getaway we loved the beach the little cottage great with everything you need"
United States
Suzanne V.
BEACH COTTAGE BY THE SEA....
Outdoor dining

11. 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)
"Well equipped and super clean; great place!"
United States
Steve S.
Cozy Cottage with Private Dock- Chesapeake Bay/ Cambridge (Pet-Friendly)
Property grounds

12. 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, (15 reviews)
"The owner was very nice "
United States
karen
The price is AED 562
AED 989 total
includes taxes & fees
26 Aug - 27 Aug
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.
Exterior

13. Beachfront Hideaway - Pet Friendly, Hot Tub, EV

Beachfront Hideaway - Pet Friendly, Hot Tub, EV
Lottsburg
9.6 out of 10, Exceptional, (23 reviews)
"No complaints. The owners make a lot of efforts to make your stay pleasant, like a closet with extra batteries, sunscreen, etc. Kitchen has a lot of extras like 3 different types of coffee makers. The views are amazing and its nice to have a bit of lawn to walk the dogs around. "
United States
Ann Marie M.
Beachfront Hideaway - Pet Friendly, Hot Tub, EV
Terrace/patio

14. Sunrise Waterfront Cottage in Beautiful Hoopers Island

Sunrise Waterfront Cottage in Beautiful Hoopers Island
Fishing Creek
10.0 out of 10, Exceptional, (88 reviews)
"It is a beautiful place to visit!"
United States
Yoon G.
Sunrise Waterfront Cottage in Beautiful Hoopers Island
Exterior

15. Family and Pet-Friendly, Waterfront with Pier

Family and Pet-Friendly, Waterfront with Pier
Cambridge
10.0 out of 10, Exceptional, (275 reviews)
"Rob was such a wonderful and inviting host"
United States
Stacy S.
Family and Pet-Friendly, Waterfront with Pier
Exterior

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

Grace Creek Cottage, Minutes to St. Michaels, Pool, Dock
Bozman
10.0 out of 10, Exceptional, (3 reviews)
"Beautiful, private setting, but not far from the town of St. Michaels. House was very clean and beds were comfy. The kitchen was very well equipped for preparing meals. We really enjoyed relaxing in the screened in porch and on the Adirondack chairs overlooking the water. There was so much wildlife to view: bald eagles, herons, tree frogs, crabs…We had a great time! Thank you!"
United States
Melissa B.
Grace Creek Cottage, Minutes to St. Michaels, Pool, Dock
Terrace/patio

17. 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, (21 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
Outdoor dining

18. 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, (22 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
Exterior

19. 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, (133 reviews)
"We had a great time. The house was so charming and the location was perfect. Can't wait to go back!"
United States
Anonymous traveler
John Bruff Waterview Cottage - on Harbor and on Park - In Town St. Michaels!
Exterior

20. Relaxing Waterfront Cottage Near St Michaels, Maryland

Relaxing Waterfront Cottage Near St Michaels, Maryland
Wittman
9.8 out of 10, Exceptional, (254 reviews)
"The place was very clean and comfortable. Loved the view. Would definitely stay again."
United States
Susan E.
Relaxing Waterfront Cottage Near St Michaels, Maryland
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

St Michaels Inn

St Michaels Inn

8/10 Good
"St. Michael's Inn is a nice place to stay for a few days in the area. It was a pleasant room with no big frills, but a nice clean quiet place to spend the night. The breakfast was good and the staff are all very polite and nice!"
Jennifer 1-night trip
Posted less than an hour ago
St Michaels Inn

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