Dorchester County Holiday Rentals: Short-Term Accommodations for Rent

Holiday Rentals in Dorchester County
United States of America
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Our top choices for Dorchester County holiday rentals

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

A cozy attic bedroom with a bed, a chair, a TV, and a window.

A room with a sloped ceiling, a brick accent wall, a window, and a door leading to another room.

A compact bathroom with a dark grey vanity, a white sink, and a small trash bin.

1. Sailwinds Loft at Cambridge Creek

Sailwinds Loft at Cambridge Creek

Cambridge

10.0 out of 10, Exceptional, (40 reviews)

10/10

Exceptional

(40 reviews)

"Wonderful place to stay."

Sharon D.

The price is HK$1,216

HK$1,216

HK$1,988 total

includes taxes & fees

6 Oct - 7 Oct

Sailwinds Loft at Cambridge Creek

A waterfront restaurant with outdoor seating, a dock with boats, and a building with a green awning.

A brick building with a white porch and a well-maintained lawn.

A marina with multiple boats docked, calm water, and a clear sky.

An outdoor dining area with wooden tables and chairs, surrounded by greenery and a large tree.

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)

9.4/10

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."

Robert

The price is HK$1,295

HK$1,295

HK$2,978 total

includes taxes & fees

27 Oct - 28 Oct

Cozy 2 Bedroom, 2.5 Bath across from Cambridge City Marina

A marina with multiple boats docked, a grassy area, and a small building with a red roof.

A living room with a dark gray sofa, a small round table, and a green throw blanket. There is a brick accent wall and a ceiling fan.

3. The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

Downtown Cambridge

9.8 out of 10, Exceptional, (14 reviews)

9.8/10

Exceptional

(14 reviews)

"Great stay! Gorgeous apartment!"

Kristen S.

The price is HK$1,295

HK$1,295

HK$2,978 total

includes taxes & fees

27 Oct - 28 Oct

The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

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

A covered outdoor area with large windows, a bench, and hanging items.

A white house with a large lawn and a bird sculpture on a pedestal.

A compact kitchen with a dining area, a fireplace, and a ceiling fan.

4. Waterfront Getaway with Dock

Waterfront Getaway with Dock

Woolford

10.0 out of 10, Exceptional, (67 reviews)

10/10

Exceptional

(67 reviews)

"It was perfect for our overnight on way to NY!"

Meagan G.

The price is HK$1,805

HK$1,805

HK$2,154 total

includes taxes & fees

25 Oct - 26 Oct

Waterfront Getaway with Dock

A spacious living room with a brown leather sofa, a round coffee table, and a dining area with a white table and chairs.

A bedroom with a bed, a window with curtains, a radiator, and a painting on the wall.

A modern kitchen with stainless steel appliances, wooden cabinets, and a granite countertop.

A porch with two Adirondack chairs and a table, a black door, and a window with a 'SMILE! YOU'RE ON CAMERA' sign.

5. More, than just a place to sleep - welcome home!

More, than just a place to sleep - welcome home!

Cambridge

The price is HK$2,330

HK$2,330

HK$3,133 total

includes taxes & fees

5 Oct - 6 Oct

More, than just a place to sleep - welcome home!

A spacious living room with a large TV, blue sofa, and a ceiling fan.

A long dining table with white chairs, a chandelier, and a wooden floor.

A room with large windows, two blue chairs, a white table, and a lamp.

A covered patio with wicker furniture and a wooden table, overlooking a grassy yard.

6. 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)

9.6/10

Exceptional

(35 reviews)

"Beautiful piece of property and clean, comfortable accommodations! Would definitely return if plan to be in that area again!!"

Joyce F.

The price is HK$2,726

HK$2,726

HK$5,160 total

includes taxes & fees

6 Oct - 7 Oct

The Blue Heron-Spacious Waterfront Eastern Shore getaway with kayaks

A wooden interior with a dining area, sofas, and a table.

A wooden interior with a round dining table, white chairs, a hanging light fixture, and a window with a view of houses.

A wooden hallway with a staircase, a mirror, and a small table with a bowl and flowers.

7. 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, (15 reviews)

9.0/10

Wonderful

(15 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."

Anonymous traveller

The price is HK$2,952

HK$2,952

HK$5,424 total

includes taxes & fees

6 Oct - 7 Oct

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

A spacious living room with a large window, a ceiling fan, and a view of the outdoors.

A single-story house with a front porch, a chimney, and a green door.

A bedroom with a bed, a ceiling fan, a window, and a view of the outdoors.

A modern kitchen with white cabinetry, a built-in oven, a microwave, and a coffee maker.

8. 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)

10/10

Exceptional

(16 reviews)

"very serene, peaceful home on the bay! Amazing getaway! "

Jill C.

The price is HK$2,425

HK$2,425

HK$4,608 total

includes taxes & fees

27 Oct - 28 Oct

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.

A two-story building with a central tower, a front porch, and a gravel driveway.

A large, single-story house with a central chimney, surrounded by a calm lake, reflecting the structure.

An aerial view of a coastal landscape with a river meandering through a marshy area, surrounded by sparse vegetation and a distant shoreline.

9. 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)

10/10

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."

Thomas S.

The price is HK$2,158

HK$2,158

HK$2,620 total

includes taxes & fees

19 Oct - 20 Oct

Riverside Lodge Bed & Breakfast on the Honga River UNIT C

A bedroom with a bed, a chair, and a window with curtains.

A snow-covered pier extending into a frozen body of water with a clear sky in the background.

10. 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)

10/10

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. "

Robin E.

The price is HK$1,942

HK$1,942

HK$2,358 total

includes taxes & fees

5 Oct - 6 Oct

Riverside Lodge Bed & Breakfast on the Honga River UNIT E

A room with a large bed, multiple windows, and a ceiling fan.

A kitchen with white cabinets, stainless steel appliances, a checkered floor, and a wooden chair.

A spacious living area with a round glass table, two sofas, a bookshelf, and a large painting.

A dining area with a table and chairs, a ceiling fan, and a view through a large window.

11. Salisbury Riverfront Lofts

Salisbury Riverfront Lofts

3.0 star property

Salisbury

9.4 out of 10, Exceptional, (27 reviews)

9.4/10

Exceptional

(27 reviews)

"Excellent choice for the price, recommended for larger groups."

Marcos

The price is HK$526

HK$526

HK$1,959 total

includes taxes & fees

4 Oct - 5 Oct

Salisbury Riverfront Lofts

A white building with a balcony on stilts, a metal roof, and a small tower with a light on top.

A spacious living room with a ceiling fan, a staircase, and a view of the outdoors.

A marina with boats docked, a city skyline in the background, and a calm water surface reflecting the lights.

A modern kitchen with wooden cabinets, stainless steel appliances, and a large island with a sink.

12. 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)

9.8/10

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."

Dawn G.

The price is HK$694

HK$694

HK$2,268 total

includes taxes & fees

5 Oct - 6 Oct

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

Three birds perched on a wooden structure by the water.

A kitchen with a dining area, large windows, and a view of the outdoors.

KI Beach House has many Great Rooms for Mingling or just being by yourself.

A cozy living room with a ceiling fan, a dining area with chairs and a table, and large windows offering a view of the outdoors.

13. Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!

Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!

Stevensville

10.0 out of 10, Exceptional, (75 reviews)

10/10

Exceptional

(75 reviews)

"Just what was needed for our weekend stay."

barbara s.

The price is HK$5,886

HK$5,886

HK$10,394 total

includes taxes & fees

4 Oct - 5 Oct

Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!

A beach with a rocky shoreline, a swimming area, and multi-story buildings in the background.

A dining table set with pink bowls and glasses, surrounded by chairs, with a large plant and a window in the background.

A living room with a blue sofa, a round mirror, and a coffee table.

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, (24 reviews)

10/10

Exceptional

(24 reviews)

"Cute, family friendly home. Had everything we needed for a comfortable stay."

Johanna S.

The price is HK$541

HK$541

HK$2,434 total

includes taxes & fees

4 Oct - 5 Oct

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

A grassy area with a stone path leading to a seating arrangement under trees, overlooking a body of water.

A wooden pier extending into calm water with a sunset in the background.

A room with a sofa, two chairs, a small table, a TV on a stand, a window with blinds, and a wooden door.

A pebbled beach with a wooden pier extending into calm water, surrounded by trees and grassy areas.

15. 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)

9.2/10

Wonderful

(15 reviews)

"Beautiful view from the house. Extremely clean. Had everything we needed. Can't wait to come back"

ed r.

The price is HK$1,334

HK$1,334

HK$2,253 total

includes taxes & fees

6 Oct - 7 Oct

Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

A bedroom with a bed, a fireplace, a ceiling fan, and a painting of a beach.

A room with three large windows, wicker furniture, a small table with a plant, and a patterned rug.

A single-story house with a front porch, a small window above the door, and a front yard with a bush.

A bedroom with a bed, a nightstand, a lamp, a painting, and a window.

16. 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, (8 reviews)

10/10

Exceptional

(8 reviews)

"Loved the location and the hosts' kindness and care."

Nancy P.

The price is HK$967

HK$967

HK$2,048 total

includes taxes & fees

6 Oct - 7 Oct

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

A lakeside view with chairs and a table, a rainbow, and trees.

A living room with a black leather sofa, a brown armchair, a flat-screen TV, a tall floor-standing speaker, and a sliding glass door leading to a balcony with a view of a body of water.

A sandy beach with footprints, surrounded by greenery and a calm body of water.

A compact kitchen with white cabinets, a stainless steel oven, a black stove, and a sink.

17. Bright and airy waterfront getaway

Bright and airy waterfront getaway

Benedict

9.6 out of 10, Exceptional, (25 reviews)

9.6/10

Exceptional

(25 reviews)

"Amazing host and home, great view with the water right there, and short drive to any shopping needs. It was the serene getaway I needed to recharge from city life and corporate burnout."

George

The price is HK$1,624

HK$1,624

HK$2,786 total

includes taxes & fees

4 Oct - 5 Oct

Bright and airy waterfront getaway

A backyard with a small waterfall, rocks, and a pond with lily pads. There are two blue chairs and a black pot near the waterfall.

A two-story house with a gabled roof, a front porch, and a flag.

A lakeside property with a dock, a grassy area with outdoor seating, and a small building.

A wooden staircase with a white railing, a welcome sign, and a vase with flowers on a console table.

18. Turnbridge Manor

Turnbridge Manor

Denton

9.8 out of 10, Exceptional, (18 reviews)

9.8/10

Exceptional

(18 reviews)

"Really nice place and you can walk to everything.Will stay again!"

Glenn S.

The price is HK$2,825

HK$2,825

HK$4,783 total

includes taxes & fees

6 Oct - 7 Oct

Turnbridge Manor

A pathway lined with trees and lights leading to a wooden building with a visible window.

A modern room with a large sliding glass door leading to an outdoor area, a small wooden bench, a fluffy white floor lamp, and a potted plant on a white console table.

A modern kitchen with a built-in stove, a dining area with a long table, and large windows offering a view of the outdoors.

A wooden staircase leading to a deck with string lights, surrounded by trees.

19. Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay

Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay

Lusby

9.6 out of 10, Exceptional, (14 reviews)

9.6/10

Exceptional

(14 reviews)

"Nice house in a great location. Great for groups."

Anonymous traveller

The price is HK$3,625

HK$3,625

HK$6,678 total

includes taxes & fees

12 Oct - 13 Oct

Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay

An open door leading to a bedroom with a bed, a nightstand, and a lamp.

A kitchen with white cabinets, a black stove, a microwave, a refrigerator, and a checkered floor.

A kitchen with white cabinetry, a granite countertop, a sink, and a backsplash.

A living room with a glass coffee table, two sofas, a rug, a painting, and a bookshelf.

20. Stylish 2 bedroom 1 bath with riverfront views close to dining and downtown

Stylish 2 bedroom 1 bath with riverfront views close to dining and downtown

Salisbury

9.8 out of 10, Exceptional, (25 reviews)

9.8/10

Exceptional

(25 reviews)

"Great location with plenty of space to relax."

Doug R.

The price is HK$549

HK$549

HK$1,409 total

includes taxes & fees

4 Oct - 5 Oct

Stylish 2 bedroom 1 bath with riverfront views close to dining and downtown

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

avid hotel California - Lexington Park by IHG

10/10 Excellent

"Friendly and helpful staff. Easy parking and clean room. Breakfast bar well maintained."

Robert 3-night trip

Posted 15 hours ago

avid hotel California - Lexington Park by IHG

Hampton Inn Salisbury

10/10 Excellent

"Nice and quiet. Super quick check in. Will stay again."

jason 1-night trip

Posted 17 hours ago

Hampton Inn Salisbury

St Michaels Inn

10/10 Excellent

"Late night manager was extremely helpful!"

Rodney 1-night trip

Posted 2 days ago

St Michaels Inn

Tru by Hilton Georgetown

10/10 Excellent

"This is a clean, modern, Spartan hotel that was a good stopping off point on our way to Ocean City, Maryland. Don't expect over the top opulance if you stay here. Everything works - shower, bed, breakfast, television - and all is very well done. We had no problems at all."

John 1-night trip

Posted 2 days ago

Tru by Hilton Georgetown

Microtel Inn & Suites By Wyndham Georgetown Delaware Beaches

8/10 Good

"Our toilet rocked back and forth and the handle in the shower came off in my hand. Tub had a big patch that had been covered with a hard, sharp glue"

Dawn 3-night trip

Posted 5 days ago

Microtel Inn & Suites By Wyndham Georgetown Delaware Beaches

Days Inn & Suites by Wyndham Seaford

10/10 Excellent

"Clean and well maintained property."

Tanya 1-night trip

Posted 5 days ago

Days Inn & Suites by Wyndham Seaford

Best Western Salisbury Plaza

8/10 Good

"I would have preferred non plastic plates and flatware"

Sarah 1-night trip

Posted 11 days ago

Best Western Salisbury Plaza

Cambridge Inn

10/10 Excellent

"Good, clean room for a reasonable rate!"

Alexander 3-night trip

Posted 12 days ago

Cambridge Inn

Pet Friendly Delightful Waterfront Cottage on Hoopers Island, MD.

10/10 Excellent

"This was a return trip for me, as always the property was clean, comfortable, quiet, The communication with the host was excellent, and we’ll definitely be back in the future to enjoy the gem that Hoopers Island is. Thank you for sharing your property again."

John M. 2-night trip

Posted 3 months ago

Pet Friendly Delightful Waterfront Cottage on Hoopers Island, MD.

Dorchester County Holiday Rentals

Change your mind

Treat yourself

Be picky

Our top choices for Dorchester County holiday rentals

1. Sailwinds Loft at Cambridge Creek

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

3. The Drinking Gourd: Stunning Penthouse in Historic Downtown Cambridge

4. Waterfront Getaway with Dock

5. More, than just a place to sleep - welcome home!

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

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

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

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

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

11. Salisbury Riverfront Lofts

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

13. Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!

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

15. Peaceful Suite on the Water "Osprey." Sunrise over the river from your porch.

16. 3-bedroom house in soothing Saint Leonard with AC for relaxing stays

17. Bright and airy waterfront getaway

18. Turnbridge Manor

19. Lakefront A-Frame: Private Dock, Kayaks & Sauna – Sleeps 12, Chesapeake Bay

20. Stylish 2 bedroom 1 bath with riverfront views close to dining and downtown

Find holiday rentals that suit your style

Top Dorchester County Hotel Reviews

avid hotel California - Lexington Park by IHG

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