Hillsboro Holiday Rentals, Maryland: Private House Rentals

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Our top choices for Hillsboro hotels

A modern lobby with a stone fireplace, a blue patterned rug, a blue sofa with colorful cushions, a brown leather chair, and a round coffee table.

A hotel with a covered entrance, multiple floors, and a parking lot.

An indoor swimming pool with clear water, marked depth lines, and a lifeguard chair.

A hotel lobby with a large wooden reception desk, multiple seating areas, a television, and a patterned carpet.

1. Fairfield Inn & Suites by Marriott Easton

Easton

Amanda

3.498.358 ₫

3.848.193 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A swimming pool with a metal ladder, lounge chairs, and a small building in the background.

A hotel with a prominent 'Best Western' sign, a brick facade, and a covered entrance.

A hotel room with a bed, a sofa, a desk, and a chair. There are two lamps on the nightstands, a television, and a window with curtains.

A hotel lobby with a reception desk, seating area, and a large wall mural.

2. Best Western Denton Inn

Denton

Courtney

2.950.890 ₫

3.275.488 ₫ total

includes taxes & fees

15 Nov - 16 Nov

A hotel room with two beds, a wooden headboard, a nightstand with a lamp, and a framed picture on the wall.

A coffee station with two coffee machines and a variety of coffee pods and cups.

A reception area with two reception desks, a wall-mounted sign reading "Holiday Inn Express," and a telephone on the right side.

3. Holiday Inn Express Easton by IHG

Easton

Alison

3.858.802 ₫

4.244.682 ₫ total

includes taxes & fees

25 Oct - 26 Oct

A spacious living room with a fireplace, a sofa, a coffee table, and a staircase leading to another level.

A hotel with a brick facade, multiple parking spaces, and a landscaped area with trees.

A hotel room with a sofa, armchair, and a small table. There is a lamp on a side table, and a door leading to another room.

A hotel pool area with multiple pools, lounge chairs, and a pool lift.

4. Best Western Plus Easton Inn & Suites

Easton

Donna

3.081.862 ₫

3.390.048 ₫ total

includes taxes & fees

15 Nov - 16 Nov

A hotel room with a large bed, a desk, a chair, a television, and a window with curtains.

A swimming pool with lounge chairs and umbrellas, surrounded by a fence and buildings.

A covered outdoor seating area with brick walls, two potted plants, and a table and chairs.

A gym with a treadmill, elliptical, and stationary bike.

5. Baymont by Wyndham Easton

Easton

Edwin

2.306.353 ₫

2.536.988 ₫ total

includes taxes & fees

21 Oct - 22 Oct

A modern hotel dining area with a long table, four chairs, and three pendant lights.

A hotel lobby with a reception desk, a dining area with chairs and a table, and a seating area with a sofa and armchairs.

A hotel hallway with carpeted floors, white doors, and overhead lighting.

A swimming pool with a tiled edge, a lifeguard chair, and a sign on the wall.

6. Hampton Inn Easton

Easton

Andrew

3.311.836 ₫

3.643.071 ₫ total

includes taxes & fees

29 Oct - 30 Oct

A large, stately house with a grand entrance, multiple windows, and a symmetrical facade.

A bedroom with a large bed, a nightstand, a lamp, and a window with blinds.

A spacious dining area with multiple tables and chairs, wooden ceiling beams, and large windows with blinds.

An indoor corridor with brick walls, a brick floor, and a sign reading "DECANTER WINE ROOM".

7. The Tidewater Inn

Easton

Miriam

4.633.415 ₫

5.096.756 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A rooftop terrace with wicker furniture, a fire pit, and a view of a marina.

A waterfront hotel with multiple balconies, a dock with boats, and outdoor seating areas.

An outdoor event area with round tables and a view of the water.

8. Hyatt Place Kent Narrows & Marina

Grasonville

Joseph

3.934.520 ₫

4.367.317 ₫ total

includes taxes & fees

25 Oct - 26 Oct

A hotel room with two beds, a desk, a TV, and a window with curtains.

A covered corridor with a series of doors, each marked with a number.

A building with a sign reading "EcoLodge."

A breakfast bar with a waffle maker, coffee machine, and juice dispenser.

9. Econo Lodge Easton Route 50

Easton

Adriana

1.980.938 ₫

2.179.031 ₫ total

includes taxes & fees

18 Nov - 19 Nov

A hotel room with a sofa, armchairs, a TV, a bed, and a large window.

A breakfast bar with waffle and juice dispensers, a refrigerator, and a trash bin.

A hotel room with a sofa, armchairs, a desk with a computer, a TV, and a plant.

A Quality Inn hotel with a sign, a lawn, and a building with a clock tower.

10. Quality Inn Grasonville near Kent Island

Grasonville

Crystal

2.159.844 ₫

2.397.427 ₫ total

includes taxes & fees

15 Nov - 16 Nov

A patio with outdoor seating, overlooking a marina with boats.

A waterfront hotel with multiple balconies, a marina with yachts, and a well-lit exterior.

An indoor swimming pool with clear views of boats and water.

A marina with multiple boats docked, a Hilton Garden Inn hotel, and a parking area.

11. Hilton Garden Inn Kent Island Marina

Grasonville

Charles

3.247.532 ₫

3.604.760 ₫ total

includes taxes & fees

18 Nov - 19 Nov

A large, two-story Victorian-style house with a prominent tower, multiple windows, and a porch.

A group of people toasting at a round table in a room with large windows and artwork on the walls.

A living room with a sofa, a chair, a small table with a plant, and a window with a view of buildings.

A bedroom with a sloped ceiling, a wooden bed, a desk with a lamp, and a dresser.

12. Hummingbird Inn

Easton

Todd

7.664.549 ₫

8.726.093 ₫ total

includes taxes & fees

10 Nov - 11 Nov

Two Adirondack chairs facing a calm body of water with a clear sky above.

A hotel room with a large bed, a desk with a flat-screen TV, a chair, a small table with a lamp, and a window with curtains.

A reception desk with a modern design, a digital display, and a check-in counter.

A modern food court with a central island, various food stations, and a yogurt display.

13. Holiday Inn Express Annapolis East-Kent Island by IHG

Grasonville

Marc

2.717.925 ₫

3.016.896 ₫ total

includes taxes & fees

8 Nov - 9 Nov

A gym with exercise equipment, a bench, and a wall-mounted mirror.

A lobby with a reception desk, a clock, and a wall-mounted deer head.

14. Best Western Kent Narrows Inn

Grasonville

Beth

2.326.544 ₫

2.582.464 ₫ total

includes taxes & fees

8 Nov - 9 Nov

A room with a fireplace, a dining area with chairs, a large window with a view of the outside, and a cabinet with bottles.

A hotel room with a large bed, a chair, a desk, and a television.

A swimming pool with white lounge chairs and blue umbrellas, surrounded by trees.

A living room with a fireplace, a sofa, a coffee table, and a television mounted on the wall.

15. Inn at Perry Cabin

Downtown St. Michaels

Virgilio

12.712.867 ₫

13.984.153 ₫ total

includes taxes & fees

18 Nov - 19 Nov

A modern kitchen with wooden cabinets, a stainless steel refrigerator, and a large island with stools.

A white colonial-style house with a covered porch, brick steps, and outdoor seating.

A banquet hall with round tables set for dining, large windows with a view of a lake, and white chairs.

A deck with wicker furniture, a table, and an umbrella, overlooking a lake with trees and a dock.

16. The Oaks Waterfront

Easton

Jeffrey

11.391.989 ₫

12.531.188 ₫ total

includes taxes & fees

21 Oct - 22 Oct

A two-story house with a porch, a front door, and a small garden area.

A two-story building with a balcony on the upper floor, outdoor seating with wooden chairs and tables, and a clear view of the surrounding area.

A dark wooden panel wall with a mounted flat-screen TV, a bench with cushions, and a small plant in a vase.

A neatly made bed with white linens and a beige pillow, a straw hat on the bed, a wooden nightstand with a small plant and a glass, and a wall-mounted light fixture.

17. The Wildset

Downtown St. Michaels

Sarah

5.927.665 ₫

7.167.557 ₫ total

includes taxes & fees

9 Nov - 10 Nov

A two-story building with a covered entrance and an American flag.

A restaurant with a bar area, multiple seating arrangements, and a kitchen visible in the background.

A rectangular swimming pool with a white edge, a covered patio area with outdoor furniture, and a flagpole with two flags.

18. St Michaels Inn

St. Michaels

Lynn

2.073.388 ₫

2.280.726 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A modern kitchen with a large island, pendant lights, and a view to the outside.

A covered outdoor seating area with tables and chairs, a pathway leading to it, and a landscaped garden.

A spacious living room with a sofa, coffee table, and dining area.

A row of white single-story houses with dark roofs, a paved driveway, and a grassy lawn.

19. Queenstown Harbor Golf Resort

Queenstown

9.631.550 ₫

10.979.967 ₫ total

includes taxes & fees

2 Nov - 3 Nov

A two-story house with a swimming pool, outdoor seating, and a covered patio area.

A dining room with a red tablecloth, wooden chairs, and a vase of pink lilies.

A living room with a fireplace, a sofa, a chair, and a bookshelf.

A four-poster bed with a floral bedspread, a large bathtub, and a chair in a room with green walls and wooden floors.

20. George Brooks House B&B

St. Michaels

Erin

5.011.263 ₫

5.512.389 ₫ total

includes taxes & fees

2 Nov - 3 Nov

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Top Hillsboro Hotel Reviews

Holiday Inn Express Easton by IHG

10/10 Excellent

"Mic clean room with warm breakfast"

St Michaels Inn

10/10 Excellent

"Staff was exceptional. Historical vibe was fun and coastal-appropriate. Close to DC and other fun destinations."

Best Western Kent Narrows Inn

10/10 Excellent

"We were in town for a wedding. The hotel was close to the venue which is why we chose it. The staff was very friendly upon check in, the room was very clean, nice bathroom, comfortable bed and the view of the bay from our room was fabulous! The included breakfast was the standard breakfast items but very good!"

Hummingbird Inn

10/10 Excellent

"Adorable property in Easton, MD (a hidden gem) with a lovely staff and great breakfast included. Great for a romantic trip away!"

The Wildset

10/10 Excellent

"Loved my stay at Wildset. Place is very clean, cozy & comfortable. Staff very friendly. Convenience to everything in town. Only 2 issues I had was how long it took shower water to get hot. And it wasn’t super hot. Not sure if it was cause I was in main building. Other was a knocking noise which seemed to happen primarily while restaurant was open. Not sure if it was from the dishwasher or some other equipment. I’m a light sleeper too so some people may be able to sleep thru it. Would def stay here again!!"

Hampton Inn Easton

10/10 Excellent

"Pet friendly...very nice for our dog Staff helpful"

The Tidewater Inn

8/10 Good

"This hotel is a gorgeous historic hotel. It has all character and beauty that you expect in Easton, Maryland. People should be aware that the air conditioning/heat is controlled by the staff. So if it’s hot in the room, you can’t adjust the air conditioning."

Holiday Inn Express Annapolis East-Kent Island by IHG

8/10 Good

"Nice location. Good staff. Pet friendly +++"

Best Western Denton Inn

10/10 Excellent

"Terrific breakfast options. Great Belgian waffles"