Hillsboro Holiday Rentals, Maryland: Private House Rentals

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Our top choices for Hillsboro hotels

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

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

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

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

1. Best Western Denton Inn

Denton

Courtney

฿3,829

฿4,250 total

includes taxes & fees

12 Nov - 13 Nov

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.

An outdoor patio with tables and chairs, a large umbrella, and a brick building in the background.

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

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

2. Fairfield Inn & Suites by Marriott Easton

Easton

Amanda

฿4,517

฿4,969 total

includes taxes & fees

25 Oct - 26 Oct

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.

A modern hotel lobby with multiple seating areas, including tables and chairs, and a reception desk.

3. Holiday Inn Express Easton by IHG

Easton

Alison

฿4,980

฿5,478 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 pool area with multiple pools, lounge chairs, and a pool lift.

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 lobby with a sofa, dining tables, chairs, a coffee station, and artwork on the walls.

4. Best Western Plus Easton Inn & Suites

Easton

Donna

฿3,997

฿4,396 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 gym with a treadmill, elliptical, and stationary bike.

A hotel kitchen with a brick wall, a framed sailboat artwork, a coffee station, and wooden cabinets.

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

5. Baymont by Wyndham Easton

Easton

Edwin

฿2,978

฿3,276 total

includes taxes & fees

21 Oct - 22 Oct

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

A Hampton Inn hotel with a brick facade, a large entrance, and a flagpole.

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.

6. Hampton Inn Easton

Easton

Andrew

฿4,274

฿4,702 total

includes taxes & fees

29 Oct - 30 Oct

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

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

A modern hotel lobby with a bar area, seating arrangements, and large windows offering city views.

7. Hyatt Place Kent Narrows & Marina

Grasonville

Joseph

฿5,080

฿5,639 total

includes taxes & fees

26 Oct - 27 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.

A spacious living room with a leather sofa, a coffee table, and a bookshelf filled with books.

8. The Tidewater Inn

Easton

Miriam

฿5,983

฿6,581 total

includes taxes & fees

1 Nov - 2 Nov

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

A spacious lobby with a staircase, a reception desk, and a dining area.

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

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

9. Quality Inn Grasonville near Kent Island

Grasonville

Crystal

฿2,802

฿3,111 total

includes taxes & fees

15 Nov - 16 Nov

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

A building with a sign reading "EcoLodge."

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

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

10. Econo Lodge Easton Route 50

Easton

Adriana

฿2,569

฿2,826 total

includes taxes & fees

18 Nov - 19 Nov

A kitchenette with a coffee machine, a framed picture, and a potted plant.

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

11. Best Western Kent Narrows Inn

Grasonville

Beth

฿3,004

฿3,335 total

includes taxes & fees

8 Nov - 9 Nov

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

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

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

A spacious dining area with a large rectangular table, multiple chairs, and a chandelier.

12. Hilton Garden Inn Kent Island Marina

Grasonville

Charles

฿4,186

฿4,646 total

includes taxes & fees

18 Nov - 19 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 modern food court with a central island, various food stations, and a yogurt display.

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

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

Grasonville

Marc

฿3,510

฿3,896 total

includes taxes & fees

8 Nov - 9 Nov

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

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

A turquoise bicycle with a basket and a seat, parked on a paved path with a sign for Hummingbird Inn in the background.

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

14. Hummingbird Inn

Easton

Todd

฿9,897

฿11,268 total

includes taxes & fees

21 Oct - 22 Oct

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 golf course with a water hazard and surrounding 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

฿16,486

฿18,135 total

includes taxes & fees

18 Nov - 19 Nov

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

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

A restaurant with long tables set for dining, benches along the walls, and large windows allowing natural light.

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.

16. The Wildset

Downtown St. Michaels

Sarah

฿7,691

฿9,300 total

includes taxes & fees

3 Nov - 4 Nov

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

A reception desk with a wooden finish, a sign reading "St. Michaels Inn", and a staircase leading to upper floors.

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

A hotel room with two beds, a chair, and a painting on the wall.

17. St Michaels Inn

St. Michaels

Lynn

฿2,677

฿2,945 total

includes taxes & fees

1 Nov - 2 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 wooden console table with framed floral artwork, two lamps, and two ottomans.

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

18. The Oaks Waterfront

Easton

Jeffrey

฿14,710

฿16,181 total

includes taxes & fees

26 Oct - 27 Oct

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

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

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

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

19. Queenstown Harbor Golf Resort

Queenstown

฿12,437

฿14,178 total

includes taxes & fees

2 Nov - 3 Nov

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

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

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

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

฿6,499

฿7,149 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!"

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"

Baymont by Wyndham Easton

10/10 Excellent

"Staff who received us was very helpful and respectful. Breakfast was great, rooms are well maintained and clean."