Hillsboro Holiday Rentals, Maryland: Private House Rentals

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Go beyond your typical stay in Hillsboro

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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 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.

1. Fairfield Inn & Suites by Marriott Easton

Easton

Amanda

Rp2.418.374

Rp2.660.211 total

includes taxes & fees

11 Oct - 12 Oct

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

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.

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

2. Best Western Denton Inn

Denton

Courtney

Rp2.124.913

Rp2.358.654 total

includes taxes & fees

8 Oct - 9 Oct

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

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

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

3. Holiday Inn Express Easton by IHG

Easton

Emily

Rp2.397.796

Rp2.637.576 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 lobby with a sofa, dining tables, chairs, a coffee station, and artwork on the walls.

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

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

4. Best Western Plus Easton Inn & Suites

Easton

Raheem

Rp2.308.326

Rp2.539.159 total

includes taxes & fees

4 Oct - 5 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 swimming pool with a tiled edge, a lifeguard chair, and a sign on the wall.

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

5. Hampton Inn Easton

Easton

Rachel

Rp2.288.285

Rp2.517.149 total

includes taxes & fees

11 Oct - 12 Oct

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

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.

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

6. Baymont by Wyndham Easton

Easton

Ellen

Rp1.594.355

Rp1.753.790 total

includes taxes & fees

4 Oct - 5 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

Rp3.215.914

Rp3.537.505 total

includes taxes & fees

1 Nov - 2 Nov

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.

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

8. Hyatt Place Kent Narrows & Marina

Grasonville

Karen

Rp2.719.888

Rp3.019.075 total

includes taxes & fees

18 Oct - 19 Oct

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

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

9. Quality Inn Grasonville near Kent Island

Grasonville

Crystal

Rp1.724.736

Rp1.914.457 total

includes taxes & fees

1 Nov - 2 Nov

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

A building with a sign reading "EcoLodge."

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

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

10. Econo Lodge Easton Route 50

Easton

Brady

Rp1.449.235

Rp1.594.158 total

includes taxes & fees

13 Oct - 14 Oct

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.

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

11. Hilton Garden Inn Kent Island Marina

Grasonville

roney

Rp2.626.481

Rp2.915.394 total

includes taxes & fees

12 Oct - 13 Oct

A room with a view of a wooden deck and a gazebo by the water.

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.

12. Inn at Perry Cabin

Downtown St. Michaels

Virgilio

Rp9.501.714

Rp10.451.885 total

includes taxes & fees

26 Oct - 27 Oct

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

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

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 Holiday Inn Express building with a brick facade, illuminated signage, and a parking lot with SUVs.

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

Grasonville

Marc

Rp1.850.498

Rp2.054.053 total

includes taxes & fees

1 Nov - 2 Nov

A hotel room with a bed, a desk, a chair, a large window with curtains, a wall-mounted painting, and a bathtub.

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

A wooden pavilion with picnic tables and benches, a grill, and a red bench.

A poolside area with lounge chairs and a mural of a sunset over water.

14. Best Western Kent Narrows Inn

Grasonville

Beth

Rp1.941.320

Rp2.154.865 total

includes taxes & fees

4 Oct - 5 Oct

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

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.

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

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.

15. The Wildset

Downtown St. Michaels

Sarah

Rp4.114.214

Rp4.974.785 total

includes taxes & fees

2 Nov - 3 Nov

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

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

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

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

16. Hummingbird Inn

Easton

Ann

Rp5.298.413

Rp6.032.246 total

includes taxes & fees

4 Oct - 5 Oct

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

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

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.

17. The Oaks Waterfront

Easton

Jeffrey

Rp7.875.149

Rp8.662.664 total

includes taxes & fees

13 Oct - 14 Oct

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

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

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

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

18. St Michaels Inn

St. Michaels

Lynn

Rp1.594.355

Rp1.753.790 total

includes taxes & fees

4 Oct - 5 Oct

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 two-story house with a wrap-around porch, multiple chimneys, and a well-maintained front yard.

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

19. George Brooks House B&B

St. Michaels

Erin

Rp3.476.421

Rp3.824.063 total

includes taxes & fees

2 Nov - 3 Nov

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

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

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

A golf course with water hazards, surrounded by residential houses.

20. Queenstown Harbor Golf Resort

Queenstown

Rp5.156.961

Rp5.878.935 total

includes taxes & fees

1 Nov - 2 Nov

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Top Hillsboro Hotel Reviews

Best Western Plus Easton Inn & Suites

8/10 Good

"Breakfast was great ! Staff was very helpful"

St Michaels Inn

10/10 Excellent

"Late night manager was extremely helpful!"

Baymont by Wyndham Easton

10/10 Excellent

"Great"

Hilton Garden Inn Kent Island Marina

10/10 Excellent

"Had a good time. Nice area"

Inn at Perry Cabin

10/10 Excellent

"Outstanding experience in every way. Staff was superior — everyone greeted us by name and was eager to ensure we had everything we needed. Meals at Stars were excellent — and the gorgeous views of the water and property enhanced the dining experience. The lit firepits and comfy seating outside were a welcome retreat in the early evening so we could sit and take in the views. We strolled the grounds via the walking paths and enjoyed the lush gardens and plantings. All in all, an amazing getaway."

Holiday Inn Express Easton by IHG

8/10 Good

"Hotel was nice…My only complaint was you can hear whomever was outside of your door or near your room…Other than that the stay was good."

Holiday Inn Express Annapolis East-Kent Island by IHG

10/10 Excellent

"Pet friendly. Full breakfast. Desk was accommodating for a ground floor room for my dog. Room was clean and comfortable."

Hampton Inn Easton

10/10 Excellent

"Good place all in all"

George Brooks House B&B

8/10 Good

"We enjoyed our stay but found a few things that could have been better. Our host (Will) was not present the first day and most likely did not know the coffee and tea bar had sour milk and no sugar. I took it upon myself to rummage around and find these things but I would have liked it better if they were there. Also, we had a scrap of toilet paper in our room and no refills so I had to find that as well. Small things but not a good first impression. Otherwise, the room was very comfortable, the pool was great and the breakfast was delicious."

More cheap stays in Hillsboro

St Michaels Inn

1228 S Talbot Street St. Michaels MD

Rp1.594.355

Rp1.753.790 total

4 Oct - 5 Oct

includes taxes & fees

8/10 Very good! (1,003 reviews)

Quality Inn Grasonville near Kent Island

101 Vfw Ave Grasonville MD

Rp1.724.736

Rp1.914.457 total

1 Nov - 2 Nov

includes taxes & fees

Holiday Inn Express Annapolis East-Kent Island by IHG

1020 Kent Narrows Rd Grasonville MD

Rp1.850.498

Rp2.054.053 total

1 Nov - 2 Nov

includes taxes & fees

Best Western Kent Narrows Inn

3101 Main Street Grasonville MD

Rp1.941.320

Rp2.154.865 total

4 Oct - 5 Oct

includes taxes & fees

Best Western Plus Easton Inn & Suites

8708 Alicia Drive Easton MD

Rp2.308.326

Rp2.539.159 total

4 Oct - 5 Oct

includes taxes & fees

9.2/10 Wonderful! (1,001 reviews)

The Wildset

209 N Talbot St St. Michaels MD

Rp4.114.214

Rp4.974.785 total

2 Nov - 3 Nov

includes taxes & fees

Frequently asked questions

Where is the best place to stay in Hillsboro?

St Michaels Inn, located 17.7 mi (28.5 km) from the heart of Hillsboro, is a top choice for your stay, based on our traveller data. Two other options for your visit to the area are Best Western Kent Narrows Inn and Hilton Garden Inn Kent Island Marina. See all available top hotels, or vacation rentals in Hillsboro.

If I need to cancel my hotel reservation in Hillsboro, will I receive a refund?

Yes! The majority of hotel room reservations are refundable provided that you cancel prior to the hotel's cancellation deadline, which is usually within 24-48 hours of your check-in date. If you booked a non-refundable reservation, you might still have the option to cancel and be given a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Hillsboro.

What is staying in Hillsboro like?

Visitors will definitely enjoy all that Hillsboro has to offer. There are 171 hotels and other accommodation options in the surrounding area. Find out more about Hillsboro.

What are the top places to visit in Hillsboro?

Places to visit in the wider area include Tuckahoe State Park, Wye Landing and Avalon Theatre. You'll also find Queenstown Premium Outlets and Queenstown Harbor Golf in the area. Take a look at what more there is to see and do in Expedia's Hillsboro guide.

What's the seasonal weather like in Hillsboro?

The hottest months are usually July and August, with an average temperature of 23°C, while the coldest months are January and February, with an average of 4°C. Average annual precipitation for Hillsboro is 1355 mm.

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Book Hotels in Hillsboro on Expedia.com

Find hotels in Hillsboro, MD from Rp1.594.158

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Hillsboro

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Hillsboro hotels

1. Fairfield Inn & Suites by Marriott Easton

2. Best Western Denton Inn

3. Holiday Inn Express Easton by IHG

4. Best Western Plus Easton Inn & Suites

5. Hampton Inn Easton

6. Baymont by Wyndham Easton

7. The Tidewater Inn

8. Hyatt Place Kent Narrows & Marina

9. Quality Inn Grasonville near Kent Island

10. Econo Lodge Easton Route 50

11. Hilton Garden Inn Kent Island Marina

12. Inn at Perry Cabin

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

14. Best Western Kent Narrows Inn

15. The Wildset

16. Hummingbird Inn

17. The Oaks Waterfront

18. St Michaels Inn

19. George Brooks House B&B

20. Queenstown Harbor Golf Resort

Top Hillsboro Hotel Reviews

Best Western Plus Easton Inn & Suites

St Michaels Inn

Baymont by Wyndham Easton

Hilton Garden Inn Kent Island Marina

Inn at Perry Cabin

Holiday Inn Express Easton by IHG

Holiday Inn Express Annapolis East-Kent Island by IHG

Hampton Inn Easton

George Brooks House B&B

More cheap stays in Hillsboro

St Michaels Inn

Quality Inn Grasonville near Kent Island

Holiday Inn Express Annapolis East-Kent Island by IHG

Best Western Kent Narrows Inn

Best Western Plus Easton Inn & Suites

The Wildset

Frequently asked questions

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