𝗧𝗢𝗣 𝗛𝗼𝘁𝗲𝗹𝘀 𝗶𝗻 Church Hill from RM285 (2026) - Fully Refundable Options

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Go beyond your typical stay in Church Hill

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

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

A hotel reception area with a modern design, featuring a reception desk, a seating area, and a hallway leading to other rooms.

1. Comfort Inn & Suites Chestertown

Chestertown

Amy

RM417

RM463 total

includes taxes & fees

27 Sept - 28 Sept

A hotel entrance with a clear sky, a parking lot, and a brick building with a covered entrance.

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

A spacious living room with a fireplace, a stone accent wall, and a television mounted above it.

A hotel room with a bed, a couch, a painting, and a window with curtains.

2. Red Roof Inn & Suites Chestertown

Chestertown

Linda

RM291

RM323 total

includes taxes & fees

13 Sept - 14 Sept

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

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.

A living room with a wooden cabinet, a television, a sofa, and a dining table.

3. Driftwood Inn

Chestertown

Kathy

RM257

RM285 total

includes taxes & fees

8 Sept - 9 Sept

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

4. Best Western Denton Inn

Denton

Courtney

RM480

RM533 total

includes taxes & fees

9 Sept - 10 Sept

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

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.

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

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

5. Inn at Huntingfield Creek

Rock Hall

Christine

RM730

RM810 total

includes taxes & fees

13 Sept - 14 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 hotel room with a sofa, armchairs, a desk with a computer, a TV, and a plant.

6. Quality Inn Grasonville near Kent Island

Grasonville

Faezeh

RM404

RM449 total

includes taxes & fees

28 Sept - 29 Sept

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

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

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

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

7. The Lodge at Great Oak Landing

Chestertown

Lynda

RM437

RM499 total

includes taxes & fees

8 Sept - 9 Sept

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.

8. Hyatt Place Kent Narrows & Marina

Grasonville

Karen

RM615

RM682 total

includes taxes & fees

4 Oct - 5 Oct

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

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

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

Grasonville

Emily

RM481

RM534 total

includes taxes & fees

5 Oct - 6 Oct

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

10. Hilton Garden Inn Kent Island Marina

Grasonville

roney

RM594

RM659 total

includes taxes & fees

4 Oct - 5 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 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.

11. Haven Point Inn and Gallery

Rock Hall

Mary

RM508

RM564 total

includes taxes & fees

8 Sept - 9 Sept

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

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

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

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

12. The Inn at Chesapeake Bay Beach Club

Stevensville

scott

RM774

RM961 total

includes taxes & fees

8 Sept - 9 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 large, two-story white house with a porch and multiple windows.

13. Kent Island Resort

Stevensville

Bethany

RM652

RM861 total

includes taxes & fees

21 Sept - 22 Sept

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

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.

14. Best Western Kent Narrows Inn

Grasonville

Joshua

RM471

RM522 total

includes taxes & fees

28 Sept - 29 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.

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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

Haven Point Inn and Gallery

10/10 Excellent

"It was a great time. This property was a diamond in town. Breakfast was also amazing. Paul who is the owner is very welcoming and helpful. The room was very private overlooking the beautiful back yard and clean. The bikes at the property are a plus. We will be back soon!"

Kent Island Resort

10/10 Excellent

"Just a wonderful place, we had an amazing stay!"

Red Roof Inn & Suites Chestertown

8/10 Good

"Tv didn’t work and the place needs some updating, new carpet and some new mattresses, staff is great."

Best Western Kent Narrows Inn

8/10 Good

"A little out of date"

Hyatt Place Kent Narrows & Marina

10/10 Excellent

"Great location, very clean and staff were welcoming and helpful!"

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."

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"