Church Hill Holiday Rentals, Maryland: Private House Rentals

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Our top choices for Church Hill hotels

A rectangular swimming pool with a 3 FT depth marker, surrounded by lounge chairs and a small table.

A spacious dining area with multiple tables and chairs, a central island, and a kitchen in the background.

A Comfort Inn & Suites hotel with a brick facade, arched entryway, and a well-maintained lawn.

A brick wall with a sign stating "Washington College Founded 1782" and a tree above it.

1. Comfort Inn & Suites Chestertown

Chestertown

Amy

2.534.421 ₫

2.813.208 ₫ total

includes taxes & fees

8 Nov - 9 Nov

A hotel room with a sofa, two beds, a painting, and a lamp.

A hotel room with a bed, two bedside lamps, a sofa, a small table, and a painting on the wall.

A multi-story brick building with a covered entrance and a parking lot.

A hotel sign with a red background and white lettering, a parking lot, and a building with a brick facade.

2. Red Roof Inn & Suites Chestertown

Chestertown

Kate

1.862.551 ₫

2.067.433 ₫ total

includes taxes & fees

18 Oct - 19 Oct

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

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.

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

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

Grasonville

Marc

2.561.328 ₫

2.843.075 ₫ total

includes taxes & fees

8 Nov - 9 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 waterfront hotel with multiple balconies, a dock with boats, and outdoor seating areas.

4. Hyatt Place Kent Narrows & Marina

Grasonville

Karen

3.932.544 ₫

4.365.124 ₫ total

includes taxes & fees

19 Oct - 20 Oct

A hotel entrance with a stone facade, large glass doors, and a sign indicating it is The Inn.

A bar area with multiple seating options, a variety of bottles and glasses on shelves, and a modern chandelier.

A spacious dining area with round tables, high ceilings with ductwork, and a stone fireplace.

A residential area with a garden, a patio with outdoor furniture, and a house with a chimney.

5. The Inn at Chesapeake Bay Beach Club

Stevensville

scott

5.277.888 ₫

6.516.641 ₫ total

includes taxes & fees

2 Nov - 3 Nov

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

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

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.

6. Hilton Garden Inn Kent Island Marina

Grasonville

Charles

3.585.342 ₫

3.979.730 ₫ total

includes taxes & fees

19 Oct - 20 Oct

A lakeside picnic area with wooden benches and picnic tables, surrounded by trees and a clear sky.

A campfire in a stone fire pit by a lakeside at sunset.

A large brick building with a symmetrical facade, multiple chimneys, and a central entrance.

A marina with docked boats, a wooden walkway with railings, and a sign indicating 'D DOCK'.

7. The Lodge at Great Oak Landing

Chestertown

Sandra

2.794.176 ₫

3.194.580 ₫ total

includes taxes & fees

14 Oct - 15 Oct

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.

8. Quality Inn Grasonville near Kent Island

Grasonville

Crystal

2.336.759 ₫

2.593.802 ₫ total

includes taxes & fees

8 Nov - 9 Nov

A laundry room with a stainless steel refrigerator, two white LG washing machines, and a small shelf.

A hotel room with a bed, a desk, a flat-screen TV, and artwork on the walls.

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

9. Best Western Kent Narrows Inn

Grasonville

Beth

2.325.375 ₫

2.581.166 ₫ total

includes taxes & fees

8 Nov - 9 Nov

A row of motel rooms with stone walls and red doors.

A two-story building with a brick facade, large windows, and a sloped roof.

A living room with two patterned armchairs, a wooden coffee table, and a standing fan.

A hotel room with a bed, a small refrigerator, a lamp, a picture on the wall, and a curtain.

10. Driftwood Inn

Chestertown

Kathy

1.642.872 ₫

1.823.717 ₫ total

includes taxes & fees

12 Oct - 13 Oct

A boat deck with a white bench and a view of a calm lake and distant trees.

A modern living room with a large sofa, a small armchair, a coffee table, and a fireplace.

A buffet with various food items including fruits, pastries, and salads.

A large white barn with a star on the side, surrounded by a field of sunflowers, and a large house with a green roof in the background.

11. Inn at Huntingfield Creek

Rock Hall

Christine

9.883.880 ₫

12.264.621 ₫ total

includes taxes & fees

11 Oct - 12 Oct

A two-story house with a covered porch, a staircase, and a garden area.

A dining room with a long wooden table set for six, surrounded by chairs. There are framed pictures on the walls, a window with a view of trees, and a sofa in the background.

A bedroom with a bed, a ceiling fan, a door, a chair, and a wall with three framed pictures.

A row of stationary bicycles with green frames and white seats, parked outdoors.

12. Haven Point Inn and Gallery

Rock Hall

Joe

3.457.793 ₫

3.838.150 ₫ total

includes taxes & fees

13 Oct - 14 Oct

A large, two-story barn-style building with a covered front porch and a garage.

A rectangular swimming pool with a blue interior, surrounded by white fences and shaded by trees.

A dining room with a round table set for six, surrounded by wooden chairs. A fireplace with ornate details is visible, and a large mirror hangs above it.

A large, two-story white house with a porch and multiple windows.

13. Kent Island Resort

Stevensville

Bethany

3.131.361 ₫

4.330.255 ₫ total

includes taxes & fees

28 Oct - 29 Oct

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 golf course with water hazards, surrounded by residential houses.

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

14. Queenstown Harbor Golf Resort

Queenstown

9.626.712 ₫

10.974.384 ₫ 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 restaurant with a bar area, seating, and a kitchen in the background.

15. Best Western Denton Inn

Denton

Courtney

3.072.300 ₫

3.410.253 ₫ total

includes taxes & fees

13 Oct - 14 Oct

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Stay near popular Church Hill attractions

Cassinelli Winery and Vineyards

You can enjoy a tasting or tour at Cassinelli Winery and Vineyards during your travels to Church Hill. Take in the festivals while you're in the area.

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Church Hill Theatre

You can make plans for a show at Church Hill Theatre on your trip to Church Hill.

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Top Church Hill Hotel Reviews

Best Western Kent Narrows Inn

10/10 Excellent

"For hotel employees — do hotels actually keep internal notes/ratings about guests? Like behavior, complaints, being rude, special requests, etc.? Just curious how much gets tracked behind the scenes. Upvote 195 Downvote 170 Go to comments"

Quality Inn Grasonville near Kent Island

8/10 Good

"Bed was very comfortable and the bedding was clean/new. Breakfast was great. Right off Rt 50 with a Dennys only steps away. Minor flaws- no elevator and the vending machines only took cash."

The Lodge at Great Oak Landing

10/10 Excellent

"This is a wonderful facility for a couple or family. The restaurant is just "ok"."

Kent Island Resort

10/10 Excellent

"Excellent time, loved the property and speaking with the staff who were always helpful and friendly. Our room was beautiful and just added to the experience."

More cheap stays in Church Hill

Red Roof Inn & Suites Chestertown

160 Scheeler Rd Chestertown MD

1.862.551 ₫

2.067.433 ₫ total

18 Oct - 19 Oct

includes taxes & fees

Best Western Kent Narrows Inn

3101 Main Street Grasonville MD

2.325.375 ₫

2.581.166 ₫ total

8 Nov - 9 Nov

includes taxes & fees

Quality Inn Grasonville near Kent Island

101 Vfw Ave Grasonville MD

2.336.759 ₫

2.593.802 ₫ total

8 Nov - 9 Nov

includes taxes & fees

7.8/10 Good! (987 reviews)

Comfort Inn & Suites Chestertown

150 Scheeler Road Chestertown MD

2.534.421 ₫

2.813.208 ₫ total

8 Nov - 9 Nov

includes taxes & fees

Holiday Inn Express Annapolis East-Kent Island by IHG

1020 Kent Narrows Rd Grasonville MD

2.561.328 ₫

2.843.075 ₫ total

8 Nov - 9 Nov

includes taxes & fees

Best Western Denton Inn

521 Fleetwood Rd Denton MD

3.072.300 ₫

3.410.253 ₫ total

13 Oct - 14 Oct

includes taxes & fees

Hotels in Church Hill with star rating

Frequently asked questions

What's the weather like in Church Hill?

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 Church Hill is 1223 mm.

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Book Hotels in Church Hill on Expedia.com

Find hotels in Church Hill, MD from 1.823.717 ₫

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Church Hill

Check prices for these dates

Filter by

Star rating

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Our top choices for Church Hill hotels

1. Comfort Inn & Suites Chestertown

2. Red Roof Inn & Suites Chestertown

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

4. Hyatt Place Kent Narrows & Marina

5. The Inn at Chesapeake Bay Beach Club

6. Hilton Garden Inn Kent Island Marina

7. The Lodge at Great Oak Landing

8. Quality Inn Grasonville near Kent Island

9. Best Western Kent Narrows Inn

10. Driftwood Inn

11. Inn at Huntingfield Creek

12. Haven Point Inn and Gallery

13. Kent Island Resort

14. Queenstown Harbor Golf Resort

15. Best Western Denton Inn

Stay near popular Church Hill attractions

Cassinelli Winery and Vineyards

Church Hill Theatre

Top Church Hill Hotel Reviews

Best Western Kent Narrows Inn

Quality Inn Grasonville near Kent Island

The Lodge at Great Oak Landing

Kent Island Resort

More cheap stays in Church Hill

Red Roof Inn & Suites Chestertown

Best Western Kent Narrows Inn

Quality Inn Grasonville near Kent Island

Comfort Inn & Suites Chestertown

Holiday Inn Express Annapolis East-Kent Island by IHG

Best Western Denton Inn

Hotels in Church Hill with star rating

Frequently asked questions

Explore a world of travel with Expedia

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