Church Hill Holiday Rentals, Maryland: Private House Rentals

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Our top choices for Church Hill hotels

A modern dining area with a central island, multiple tables, and chairs. There are signs for 'RISP' and 'SILVER' on the wall, and an 'EXIT' sign above a door.

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

A modern lounge area with seating, a fireplace, and a television.

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

1. Comfort Inn & Suites Chestertown

Chestertown

Amy

2.690.837 ₫

2.986.829 ₫ total

includes taxes & fees

4 Oct - 5 Oct

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.

2. Best Western Denton Inn

Denton

Courtney

3.096.288 ₫

3.436.880 ₫ total

includes taxes & fees

7 Sept - 8 Sept

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

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

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

Grasonville

Emily

3.105.305 ₫

3.446.888 ₫ total

includes taxes & fees

5 Oct - 6 Oct

A hotel room with two beds, a sofa, a coffee table, and a painting on the wall.

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

4. Red Roof Inn & Suites Chestertown

Chestertown

Linda

1.877.093 ₫

2.083.573 ₫ total

includes taxes & fees

10 Sept - 11 Sept

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 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.

5. Quality Inn Grasonville near Kent Island

Grasonville

Faezeh

2.607.400 ₫

2.894.214 ₫ total

includes taxes & fees

28 Sept - 29 Sept

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

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

6. Driftwood Inn

Chestertown

Vanesa

1.655.699 ₫

1.837.956 ₫ total

includes taxes & fees

6 Sept - 7 Sept

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

A spacious room with a large window, a seating area with a sofa and armchairs, a small table with a plant, and a display of various items including a mannequin and shelves with products.

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

Lynda

2.815.992 ₫

3.219.524 ₫ total

includes taxes & fees

8 Sept - 9 Sept

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

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

3.963.248 ₫

4.399.206 ₫ total

includes taxes & fees

4 Oct - 5 Oct

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

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.

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

9. Hilton Garden Inn Kent Island Marina

Grasonville

roney

3.827.142 ₫

4.248.128 ₫ total

includes taxes & fees

30 Sept - 1 Oct

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

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

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

A sunflower field with a white barn and a large house in the background.

10. Inn at Huntingfield Creek

Rock Hall

Christine

4.704.532 ₫

5.222.101 ₫ total

includes taxes & fees

13 Sept - 14 Sept

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

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 bedroom with a large bed, a bench, a dresser, and two windows with curtains.

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

11. Kent Island Resort

Stevensville

Margaret

4.669.853 ₫

6.082.502 ₫ total

includes taxes & fees

22 Sept - 23 Sept

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

An indoor swimming pool with a hot tub, lounge chairs, and a sunset mural on the wall.

A restaurant with a counter, seating area, and a clock on the wall.

12. Best Western Kent Narrows Inn

Grasonville

Joshua

3.033.188 ₫

3.366.839 ₫ total

includes taxes & fees

28 Sept - 29 Sept

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

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

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

A spacious living room with a fireplace, comfortable seating, and large windows offering a view of the outdoors.

13. The Inn at Chesapeake Bay Beach Club

Stevensville

scott

4.986.652 ₫

6.198.507 ₫ total

includes taxes & fees

8 Sept - 9 Sept

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

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

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

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.

14. Haven Point Inn and Gallery

Rock Hall

John

3.273.591 ₫

3.633.686 ₫ total

includes taxes & fees

8 Sept - 9 Sept

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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.

See properties

Church Hill Theatre

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

See properties

Top Church Hill Hotel Reviews

Best Western Kent Narrows Inn

10/10 Excellent

"Close to the bay"

Holiday Inn Express Annapolis East-Kent Island by IHG

10/10 Excellent

"My third stay. Hotel is clean, staff are friendly and helpful and the location is great."

Hilton Garden Inn Kent Island Marina

8/10 Good

"under beds needs better cleaning. bathroom toilet seat needs cleaning (room 519) tighten. faucet needs maintenance both tub and sink."

The Lodge at Great Oak Landing

10/10 Excellent

"Gem of a local place on the water. The rooms are big and the beds are soooo comfy. The pool is cute and the beach has bands on weekends. There are gas grills and a decent restaurant. It's not fancy (for fancy stay at the manor next door). But it's not corporate either. It's authentic, peaceful and fun."

Best Western Denton Inn

10/10 Excellent

"My stay was 10 days. Extremely professional and friendly staff. All worked hard. Clean rooms. Pool was nice. Washer-dryer worked out great. Breakfast was fresh everyday. Very good management team running this Hotel."

Haven Point Inn and Gallery

10/10 Excellent

"From getting greeted after pulling in to getting served delicious coffee, juice and breakfast before checking out everything was wonderful. Paul the inn keeper was knowledgeable and friendly. Our room was so comfortable and clean. A must if you are in the Rock Hall area."

Inn at Huntingfield Creek

10/10 Excellent

"The property was stunning. The rooms were very comfortable and the bathroom had all you need. We also really appreciated the drinks and free salted chocolate chip cookies. They were delicious. The inn keepers were and their dogs were a highlight for us. The breakfast was also absolutely delicious. Definitely would recommend this I"

Inn at Haven Harbour

10/10 Excellent

"Friendly staff at check in. This lady was helpful thru entire stay. Her name is Sharon. The Harbor had a Luau on Saturday which we attended since our son is a slip holder. Great weekend. "

More cheap stays in Church Hill

Red Roof Inn & Suites Chestertown

160 Scheeler Rd Chestertown MD

1.877.093 ₫

2.083.573 ₫ total

10 Sept - 11 Sept

includes taxes & fees

Quality Inn Grasonville near Kent Island

101 Vfw Ave Grasonville MD

2.607.400 ₫

2.894.214 ₫ total

28 Sept - 29 Sept

includes taxes & fees

Comfort Inn & Suites Chestertown

150 Scheeler Road Chestertown MD

2.690.837 ₫

2.986.829 ₫ total

4 Oct - 5 Oct

includes taxes & fees

Best Western Kent Narrows Inn

3101 Main Street Grasonville MD

3.033.188 ₫

3.366.839 ₫ total

28 Sept - 29 Sept

includes taxes & fees

8/10 Very good! (1,002 reviews)

Best Western Denton Inn

521 Fleetwood Rd Denton MD

3.096.288 ₫

3.436.880 ₫ total

7 Sept - 8 Sept

includes taxes & fees

8.6/10 Excellent! (627 reviews)

Holiday Inn Express Annapolis East-Kent Island by IHG

1020 Kent Narrows Rd Grasonville MD

3.105.305 ₫

3.446.888 ₫ total

5 Oct - 6 Oct

includes taxes & fees

9.2/10 Wonderful! (1,000 reviews)

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 1.837.956 ₫

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Church Hill

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Church Hill hotels

1. Comfort Inn & Suites Chestertown

2. Best Western Denton Inn

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

4. Red Roof Inn & Suites Chestertown

5. Quality Inn Grasonville near Kent Island

6. Driftwood Inn

7. The Lodge at Great Oak Landing

8. Hyatt Place Kent Narrows & Marina

9. Hilton Garden Inn Kent Island Marina

10. Inn at Huntingfield Creek

11. Kent Island Resort

12. Best Western Kent Narrows Inn

13. The Inn at Chesapeake Bay Beach Club

14. Haven Point Inn and Gallery

Stay near popular Church Hill attractions

Cassinelli Winery and Vineyards

Church Hill Theatre

Top Church Hill Hotel Reviews

Best Western Kent Narrows Inn

Holiday Inn Express Annapolis East-Kent Island by IHG

Hilton Garden Inn Kent Island Marina

The Lodge at Great Oak Landing

Best Western Denton Inn

Haven Point Inn and Gallery

Inn at Huntingfield Creek

Inn at Haven Harbour

More cheap stays in Church Hill

Red Roof Inn & Suites Chestertown

Quality Inn Grasonville near Kent Island

Comfort Inn & Suites Chestertown

Best Western Kent Narrows Inn

Best Western Denton Inn

Holiday Inn Express Annapolis East-Kent Island by IHG

Hotels in Church Hill with star rating

Frequently asked questions

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