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

Vacation Rentals in Dorchester County

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Our top choices for Dorchester County vacation rentals

A modern kitchen with white cabinets, a stainless steel stove, a microwave, and a sink.

1. Sailwinds Loft at Cambridge Creek

Sailwinds Loft at Cambridge Creek
Cambridge
10.0 out of 10, Exceptional, (39 reviews)
"Wonderful place to stay."
United States
Sharon D.
The price is ￥24,767
￥40,650 total
includes taxes & fees
Sep 2 - Sep 3
Sailwinds Loft at Cambridge Creek
A waterfront restaurant with outdoor seating, a dock with boats, and a building with a green awning.

2. Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina
Cambridge
9.4 out of 10, Exceptional, (25 reviews)
"Lovely terrace style town house in a lovely location in close proximity to the Marina and other amenities. Beautiful place to relax."
United States
Robert
The price is ￥23,170
￥57,081 total
includes taxes & fees
Sep 2 - Sep 3
Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

3. Pet-Friendly Pond Cottage • Nature Escape Near Beaches

Pet-Friendly Pond Cottage • Nature Escape Near Beaches
Seaford
The price is ￥19,175
￥23,713 total
includes taxes & fees
Sep 9 - Sep 10
Pet-Friendly Pond Cottage • Nature Escape Near Beaches
A spacious living room with a large window, a ceiling fan, and a view of the outdoors.

4. WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8

WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
Cambridge
10.0 out of 10, Exceptional, (16 reviews)
"very serene, peaceful home on the bay! Amazing getaway! "
United States
Jill C.
The price is ￥48,565
￥93,485 total
includes taxes & fees
Sep 3 - Sep 4
WATERFRONT!! **HOT TUB** 3 bedroom Oasis on 2+ acres - Sleeps 8
A house with a large lawn and a dock extending into a calm lake.

5. Riverside Lodge Bed & Breakfast on the Honga River UNIT C

Riverside Lodge Bed & Breakfast on the Honga River UNIT C
Fishing Creek
10.0 out of 10, Exceptional, (11 reviews)
"Peggy and Gary are the perfect hosts: welcoming, friendly, attentive and respectful of your preferences. Wonderful views of the Bay and River via the lodge -- including the cupola -- and walking around the majestic property."
United States
Thomas S.
The price is ￥43,143
￥52,337 total
includes taxes & fees
Sep 3 - Sep 4
Riverside Lodge Bed & Breakfast on the Honga River UNIT C
A wooden interior with a dining area, sofas, and a table.

6. WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE

WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE
Cambridge
9.0 out of 10, Wonderful, (14 reviews)
"Very spacious home. 4 bedrooms and 4 baths. Great basement for watching TV with a large group. Home is about 15 minutes from downtown Cambridge."
United States
Anonymous traveler
The price is ￥65,035
￥117,379 total
includes taxes & fees
Sep 29 - Sep 30
WATERFRONT!! HOT TUB!! 4 BED/4 BATH CHARMING HOME IN THE HEART OF CAMBRIDGE
A spacious living room with a large TV, blue sofa, and a ceiling fan.

7. The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
Woolford
9.6 out of 10, Exceptional, (35 reviews)
"Anne is a great host, always responded promptly regardless of time.Property is huge! Lots of patio space, and included kayaks for us to use. Next time in the area will definitely stay there"
United States
Ramon A.
The price is ￥69,029
￥122,290 total
includes taxes & fees
Sep 3 - Sep 4
The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks
A covered outdoor dining area with a table and chairs, overlooking a body of water and trees.

8. Sunset Breezes - quiet waterfront retreat

Sunset Breezes - quiet waterfront retreat
Dorchester County
10.0 out of 10, Exceptional, (45 reviews)
"Comfortable, roomy, awesome views!"
United States
John C.
The price is ￥60,034
￥75,801 total
includes taxes & fees
Sep 8 - Sep 9
Sunset Breezes - quiet waterfront retreat
A house with a large lawn and a dock extending into a calm lake.

9. Riverside Lodge Bed & Breakfast on the Honga River UNIT E

Riverside Lodge Bed & Breakfast on the Honga River UNIT E
Fishing Creek
10.0 out of 10, Exceptional, (1 review)
"We stayed Sunday - Wednesday at Riverside Lodge. The Lodge was beautiful. Breakfast was absolutely fantastic and Hooper Island was breath taking. We were able to take a boat ride to tour around the island and grad a little history and enjoy the stories. If you looking for a place to relax and renew... this is the place. "
United States
Robin E.
The price is ￥43,143
￥52,337 total
includes taxes & fees
Sep 21 - Sep 22
Riverside Lodge Bed & Breakfast on the Honga River UNIT E
A room with a large bed, multiple windows, and a ceiling fan.

10. Salisbury Riverfront Lofts

Salisbury Riverfront Lofts
3.0 star property
Salisbury
9.4 out of 10, Exceptional, (27 reviews)
"Excellent choice for the price, recommended for larger groups."
United States
Marcos
The price is ￥10,717
￥39,902 total
includes taxes & fees
Sep 15 - Sep 16
Salisbury Riverfront Lofts
A white building with a balcony on stilts, a metal roof, and a small tower with a light on top.

11. Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Stevensville
9.8 out of 10, Exceptional, (55 reviews)
"We had a wonderful stay. The house was perfect and Adam stayed in contact constantly in case we needed anything. But our stay went smoothly and we had everything we needed."
United States
Dawn G.
The price is ￥15,958
￥47,070 total
includes taxes & fees
Sep 2 - Sep 3
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
A triangular cabin with a wooden staircase leading to a door, surrounded by trees.

12. Soul Oasis - home on the Chesapeake Bay

Soul Oasis - home on the Chesapeake Bay
Lusby
10.0 out of 10, Exceptional, (59 reviews)
"Nice, clean, and would absolutely stay here again."
United States
Dusty S.
The price is ￥24,927
￥51,490 total
includes taxes & fees
Sep 30 - Oct 1
Soul Oasis - home on the Chesapeake Bay
A bedroom with a bed, a fireplace, a ceiling fan, and a painting of a beach.

13. 3-bedroom house in soothing Saint Leonard with AC for relaxing stays

3-bedroom house in soothing Saint Leonard with AC for relaxing stays
Saint Leonard
10.0 out of 10, Exceptional, (6 reviews)
"Loved the location and the hosts' kindness and care."
United States
Nancy P.
The price is ￥19,414
￥41,920 total
includes taxes & fees
Sep 2 - Sep 3
3-bedroom house in soothing Saint Leonard with AC for relaxing stays
A beach with a rocky shoreline, a swimming area, and multi-story buildings in the background.

14. Beachside Oasis with Beach Passes & King Suite by A Haven Away

Beachside Oasis with Beach Passes & King Suite by A Haven Away
North Beach
10.0 out of 10, Exceptional, (22 reviews)
"Cute, family friendly home. Had everything we needed for a comfortable stay."
United States
Johanna S.
The price is ￥17,085
￥57,482 total
includes taxes & fees
Sep 8 - Sep 9
Beachside Oasis with Beach Passes & King Suite by A Haven Away
A house with a yellow door and a window with a lamp outside.

15. Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis

Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis
Deale
8.0 out of 10, Very Good, (13 reviews)
"The rental was near our relatives in a quiet community. Neighbors were friendly. The size was perfect for me and my brother while we were in for a funeral (Arlington National). All the comforts of home! I'll definitely look to stay here again."
United States
Maude H.
The price is ￥20,853
￥52,918 total
includes taxes & fees
Sep 3 - Sep 4
Chesapeake Bay Loft Retreat, Walk to Water, Sleeps 2, 20 Min to Annapolis
An outdoor dining area with string lights, wooden tables, and chairs, overlooking a marina with boats.

16. Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants

Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
North Beach
10.0 out of 10, Exceptional, (37 reviews)
"Such a great house! "
United States
Stephanie V.
The price is ￥15,734
￥65,956 total
includes taxes & fees
Sep 2 - Sep 3
Beach House w/Yard, Beach Passes, Firepit, King Beds near Boardwalk, Restaurants
A grassy area with a stone path leading to a seating arrangement under trees, overlooking a body of water.

17. 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 ￥27,164
￥45,198 total
includes taxes & fees
Sep 8 - Sep 9
Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

18. 6 Mi to Salisbury: Forest-view Sanctuary!

6 Mi to Salisbury: Forest-view Sanctuary!
3.0 star property
Parsonsburg
The price is ￥21,092
￥43,328 total
includes taxes & fees
Sep 8 - Sep 9
6 Mi to Salisbury: Forest-view Sanctuary!

19. Family Beach House: Spacious Deck, Grill & Views

Family Beach House: Spacious Deck, Grill & Views
Chesapeak beach
9.2 out of 10, Wonderful, (7 reviews)
"Everything was great. The owner was extremely helpful. Couldn't ask for anything better."
United States
Bryan P.
The price is ￥23,010
￥73,206 total
includes taxes & fees
Sep 2 - Sep 3
Family Beach House: Spacious Deck, Grill & Views
A sandy beach with footprints, a pier in the distance, and a clear sky.

20. Tangier Escape, great place get away from it all on Deal Island, MD.

Tangier Escape, great place get away from it all on Deal Island, MD.
Deal Island Historic District
10.0 out of 10, Exceptional, (2 reviews)
"Helpful host, clean house, peaceful location! "
United States
Jennifer P.
The price is ￥17,577
￥39,804 total
includes taxes & fees
Sep 18 - Sep 19
Tangier Escape, great place get away from it all on Deal Island, MD.
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

10/10 Excellent
"There were a couple of minor details with the room but not enough to dissuade me from staying here again. Ginny on the front desk was a joy."
Alan 2-night trip
Posted 9 hours ago
St Michaels Inn

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Vacation Apartments in Dorchester County

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