Crumpton Holiday Rentals, Maryland: Private House Rentals

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Our top choices for Crumpton 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 reception area with a modern design, featuring a reception desk, a seating area, and a hallway leading to other rooms.

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.

1. Comfort Inn & Suites Chestertown

Chestertown

Amy

Rp1.879.030

Rp2.085.724 total

includes taxes & fees

25 Oct - 26 Oct

A modern building with a patio area featuring outdoor seating and a fire pit.

A modern living room with a stone fireplace, wooden ceiling, and a large TV mounted above it.

A modern living room with a stone accent wall, a flat-screen TV, a dining area with a table and chairs, and a sofa with cushions.

A modern restaurant with a long counter, multiple seating areas, and pendant lighting.

2. Fairfield Inn & Suites by Marriott Middletown

Middletown

Sharon

Rp2.120.342

Rp2.353.580 total

includes taxes & fees

4 Oct - 5 Oct

A hotel room with a sofa, armchair, ottoman, two side tables with lamps, a coffee table, a TV, and a window with curtains.

A reception desk with a sign reading "Quality Inn" and a potted plant beside it.

A breakfast buffet with a variety of food items and a bowl of fruit.

A hotel room with a sofa, a TV on a wooden stand, a lamp, and a door leading to another room.

3. Quality Inn Smyrna

Smyrna

Tonya

Rp1.522.860

Rp1.690.375 total

includes taxes & fees

27 Sept - 28 Sept

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

A living room with a fireplace, a television, and a stone accent wall.

A hotel room with a bed, a sofa, a desk, and a painting on the wall.

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

4. Red Roof Inn & Suites Chestertown

Chestertown

Linda

Rp1.282.736

Rp1.423.837 total

includes taxes & fees

5 Oct - 6 Oct

A modern building with a covered entrance, stone pillars, and a parking lot with cars.

A modern restaurant with booths and tables, a TV screen displaying AT&T, and a wooden ceiling.

A hotel lobby with a sofa, armchairs, a small table, a desk with a computer, and a TV.

A reception area with two reception desks, a glass partition, and a wall with geometric patterns.

5. Holiday Inn Express & Suites Middletown by IHG

Middletown

John

Rp1.970.760

Rp2.187.544 total

includes taxes & fees

4 Oct - 5 Oct

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

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

6. Driftwood Inn

Chestertown

Kathy

Rp1.131.443

Rp1.255.991 total

includes taxes & fees

7 Oct - 8 Oct

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 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.

7. The Lodge at Great Oak Landing

Chestertown

Jane

Rp1.924.344

Rp2.200.102 total

includes taxes & fees

27 Sept - 28 Sept

An indoor swimming pool with clear blue water, a tiled deck, and a view of the outside building.

A hotel dining area with a long wooden table, six chairs, and a fruit bowl.

A gym with treadmills, an elliptical, and a wall of dumbbells.

A large, beige hotel with a flat roof and symmetrical facade, featuring a central entrance with a covered walkway.

8. Hampton Inn Middletown

Middletown

Dwayne

Rp2.042.066

Rp2.266.693 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 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.

9. Inn at Huntingfield Creek

Rock Hall

Christine

Rp3.214.902

Rp3.568.589 total

includes taxes & fees

4 Oct - 5 Oct

A hotel room with a large bed, a black leather sofa, a wooden table, two bedside tables with lamps, and a wall-mounted air conditioner.

A room with a window displaying a menu, a sign indicating check-in and check-out times, and a chair.

A brick building with a white door labeled 'OFFICE,' a fire extinguisher mounted on the wall, and two flower planters on the sidewalk.

A parking lot with a rainbow, a building with a billboard, and a grassy area.

10. Relax Inn Smyrna Dover Coastal Gateway

Smyrna

Emily

Rp1.594.524

Rp2.040.991 total

includes taxes & fees

27 Sept - 28 Sept

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

A garden with a lawn and a table with chairs under a canopy.

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.

11. Haven Point Inn and Gallery

Rock Hall

Mary

Rp2.381.376

Rp2.643.327 total

includes taxes & fees

7 Oct - 8 Oct

A bunk bed room with white bedding and blue throw blankets.

A room with a mirror reflecting a sofa, armchair, ottoman, and a window with curtains.

A residential street lined with trees and houses.

12. Bohemia Manor Farm

Chesapeake City

Rp6.515.870

Rp6.906.822 total

includes taxes & fees

11 Oct - 12 Oct

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Stay near popular Crumpton attractions

Crumpton Park

After visiting Crumpton Park, make a plan to see the other sights and activities in Crumpton.

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Top Crumpton Hotel Reviews

Comfort Inn & Suites Chestertown

10/10 Excellent

"Overall the job couldn’t have been done better…"

Holiday Inn Express & Suites Middletown by IHG

10/10 Excellent

"Great stay, nice area"

Red Roof Inn & Suites Chestertown

10/10 Excellent

"Perfectly adequate room for a visit to Chestertown. Good furnishings and amenities. Walkable to stores and restaurants."

Quality Inn Smyrna

10/10 Excellent

"The roof was leaking on the second floor and there should be breakfast options"

The Lodge at Great Oak Landing

8/10 Good

"Unique location with a beachy feel. Comfortable with basic amenities. Communication with the lodge staff was very good as I checked in late and they sent me my room entry information. I would stay there again."

Haven Point Inn and Gallery

8/10 Good

"It was very nice they offered a homecooked breakfast with tea and coffee. However I prefer access to coffee in my room when I want it. No microwave in room, you have to go downstairs to the art gallery to use one. None of the rooms had a long mirror, Parking is a issue, especially if you have a guest come over or stop bye. Or come with more then 1 vehicle. Also would have been nice to have had soda and snack machine since the entire town shuts down early. Overall it was clean, owner was very nice, and id probably stay again."

Relax Inn Smyrna Dover Coastal Gateway

10/10 Excellent

"Good service and clean"

Hampton Inn Middletown

10/10 Excellent

"Bien"

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"

More cheap stays in Crumpton

Red Roof Inn & Suites Chestertown

160 Scheeler Rd Chestertown MD

Rp1.282.736

Rp1.423.837 total

5 Oct - 6 Oct

includes taxes & fees

7.2/10 Good! (498 reviews)

Quality Inn Smyrna

190 Stadium St, Gateway North Plaza Smyrna DE

Rp1.522.860

Rp1.690.375 total

27 Sept - 28 Sept

includes taxes & fees

7.6/10 Good! (1,001 reviews)

Relax Inn Smyrna Dover Coastal Gateway

1648 S Dupont Blvd Smyrna DE

Rp1.594.524

Rp2.040.991 total

27 Sept - 28 Sept

includes taxes & fees

7.8/10 Good! (115 reviews)

Comfort Inn & Suites Chestertown

150 Scheeler Road Chestertown MD

Rp1.879.030

Rp2.085.724 total

25 Oct - 26 Oct

includes taxes & fees

8.6/10 Excellent! (986 reviews)

Holiday Inn Express & Suites Middletown by IHG

315 Auto Park Dr Middletown DE

Rp1.970.760

Rp2.187.544 total

4 Oct - 5 Oct

includes taxes & fees

9.2/10 Wonderful! (737 reviews)

Hampton Inn Middletown

117 Sandhill Dr Middletown DE

Rp2.042.066

Rp2.266.693 total

12 Oct - 13 Oct

includes taxes & fees

8.8/10 Excellent! (926 reviews)

Frequently asked questions

What's the best place to stay in Crumpton?

Located 17.1 mi (27.5 km) from the heart of Crumpton, Fairfield Inn & Suites by Marriott Middletown is a top choice for your stay, based on our traveller data. Two other choices for your trip to the area are Red Roof Inn & Suites Chestertown and The Lodge at Great Oak Landing. See all available top hotels, or vacation rentals in Crumpton.

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

Yes! You'll find that most hotel reservations are fully refundable as long as you cancel before the accommodation's cancellation deadline, which is often 24 or 48 hours before your arrival date. If you booked a non-refundable reservation, you might be able to still cancel and get a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Crumpton.

What is staying in Crumpton like?

Travellers to Crumpton will find plenty to explore and enjoy. There are 202 hotels and other accommodation options in the surrounding area. Find out more about Crumpton.

What should I see while I'm in Crumpton?

Places to visit in the wider area include Crow Farm and Vineyard, Rolphs Wharf Marina and Historical Society of Kent County Maryland. You'll also find Chestertown Historic District and Betterton Beach in the area. Take a look at what more there is to see and do in Expedia's Crumpton guide.

What's the seasonal weather in Crumpton?

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 Crumpton is 1223 mm.

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Book Hotels in Crumpton on Expedia.com

Find hotels in Crumpton, MD from Rp1.255.991

Change your mind

Treat yourself

Be picky

Go beyond your typical stay in Crumpton

Check prices for these dates

Filter by

Star rating

Guest rating

Our top choices for Crumpton hotels

1. Comfort Inn & Suites Chestertown

2. Fairfield Inn & Suites by Marriott Middletown

3. Quality Inn Smyrna

4. Red Roof Inn & Suites Chestertown

5. Holiday Inn Express & Suites Middletown by IHG

6. Driftwood Inn

7. The Lodge at Great Oak Landing

8. Hampton Inn Middletown

9. Inn at Huntingfield Creek

10. Relax Inn Smyrna Dover Coastal Gateway

11. Haven Point Inn and Gallery

12. Bohemia Manor Farm

Stay near popular Crumpton attractions

Crumpton Park

Top Crumpton Hotel Reviews

Comfort Inn & Suites Chestertown

Holiday Inn Express & Suites Middletown by IHG

Red Roof Inn & Suites Chestertown

Quality Inn Smyrna

The Lodge at Great Oak Landing

Haven Point Inn and Gallery

Relax Inn Smyrna Dover Coastal Gateway

Hampton Inn Middletown

Inn at Huntingfield Creek

More cheap stays in Crumpton

Red Roof Inn & Suites Chestertown

Quality Inn Smyrna

Relax Inn Smyrna Dover Coastal Gateway

Comfort Inn & Suites Chestertown

Holiday Inn Express & Suites Middletown by IHG

Hampton Inn Middletown

Frequently asked questions

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