Best Crumpton Hotels in 2026 from HK$553 - Fully Refundable Options

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

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

HK$814

HK$903 total

includes taxes & fees

25 Oct - 26 Oct

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.

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

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

2. Red Roof Inn & Suites Chestertown

Chestertown

Linda

HK$565

HK$627 total

includes taxes & fees

6 Oct - 7 Oct

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

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 Fairfield by Marriott hotel with a modern design, featuring a covered entrance and multiple floors.

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

3. Fairfield Inn & Suites by Marriott Middletown

Middletown

Sharon

HK$1,012

HK$1,123 total

includes taxes & fees

4 Oct - 5 Oct

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

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

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

A hotel room with a coffee machine, a bed, and a window with a view.

4. Holiday Inn Express & Suites Middletown by IHG

Middletown

Hamlet

HK$792

HK$880 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 hotel room with a sofa, a TV on a wooden stand, a lamp, and a door leading to another room.

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

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

5. Quality Inn Smyrna

Smyrna

Tonya

HK$680

HK$754 total

includes taxes & fees

29 Oct - 30 Oct

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

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.

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

6. Hampton Inn Middletown

Middletown

DeShun

HK$894

HK$993 total

includes taxes & fees

28 Oct - 29 Oct

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

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

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.

7. Driftwood Inn

Chestertown

Kathy

HK$498

HK$553 total

includes taxes & fees

1 Oct - 2 Oct

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 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.

8. The Lodge at Great Oak Landing

Chestertown

Sandra

HK$847

HK$969 total

includes taxes & fees

1 Oct - 2 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 parking lot with a rainbow, a building with a billboard, and a grassy area.

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.

9. Relax Inn Smyrna Dover Coastal Gateway

Smyrna

Emily

HK$698

HK$894 total

includes taxes & fees

1 Oct - 2 Oct

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

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.

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

10. Inn at Huntingfield Creek

Rock Hall

Christine

HK$1,415

HK$1,571 total

includes taxes & fees

4 Oct - 5 Oct

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

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

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

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.

11. Haven Point Inn and Gallery

Rock Hall

Mary

HK$1,048

HK$1,164 total

includes taxes & fees

7 Oct - 8 Oct

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

A residential street lined with trees and houses.

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

12. Bohemia Manor Farm

Chesapeake City

HK$2,853

HK$3,024 total

includes taxes & fees

13 Oct - 14 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

Hampton Inn Middletown

10/10 Excellent

"Our room was very nice. It was clean. We were able to park near an entrance to our room. The staff was very pleasant and helpful. We would definitely stay again if we are in the area."

The Lodge at Great Oak Landing

10/10 Excellent

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

WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD

10/10 Excellent

"Property was incredibly clean, comfortable, and exactly as described. The host was absolutely wonderful—very pleasant and incredibly easy to reach. Whenever we sent a text, her response was incredibly fast, which made our stay completely stress-free. We had a great time and would definitely stay here again!""

Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows

10/10 Excellent

"We had such a wonderful experience staying here! We chose this home because our wedding was at Bohemian Manor Farm, and the location could not have been more perfect. It was so close to our venue and gave us plenty of room for our wedding party to stay together comfortably.The house was absolutely perfect for our wedding weekend, and having everyone under one roof made everything so much easier and more enjoyable. We couldn’t have asked for a better place to celebrate such a special time in our lives. We would absolutely stay here again and highly recommend it to anyone looking for a beautiful, comfortable home in the area!"

Serene Waterfront Cottage with dock and gorgeous views.

10/10 Excellent

"Home was beautiful, great views! Easily rented and all my questions answered. We crabbed right out back of the house. Made for a relaxing enjoyable long weekend."

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."

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"

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

10/10 Excellent

"We had a wonderful long weekend at the cottage. It is beautifully decorated and very clean. It was perfect for our needs. We spent our days boating on the upper bay (gorgeous weather) and evenings relaxing on the deck with a perfect view of the sunset and turkey point lighthouse. Thank you Chris and we would love to come back next season."

More cheap stays in Crumpton

Red Roof Inn & Suites Chestertown

160 Scheeler Rd Chestertown MD

HK$565

HK$627 total

6 Oct - 7 Oct

includes taxes & fees

7.2/10 Good! (500 reviews)

Quality Inn Smyrna

190 Stadium St, Gateway North Plaza Smyrna DE

HK$680

HK$754 total

29 Oct - 30 Oct

includes taxes & fees

Holiday Inn Express & Suites Middletown by IHG

315 Auto Park Dr Middletown DE

HK$792

HK$880 total

4 Oct - 5 Oct

includes taxes & fees

Relax Inn Smyrna Dover Coastal Gateway

1648 S Dupont Blvd Smyrna DE

HK$698

HK$894 total

1 Oct - 2 Oct

includes taxes & fees

7.8/10 Good! (115 reviews)

Comfort Inn & Suites Chestertown

150 Scheeler Road Chestertown MD

HK$814

HK$903 total

25 Oct - 26 Oct

includes taxes & fees

Hampton Inn Middletown

117 Sandhill Dr Middletown DE

HK$894

HK$993 total

28 Oct - 29 Oct

includes taxes & fees

8.8/10 Excellent! (929 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.

What are some of the best holiday rentals that Crumpton has to offer?

The Colonial Farmhouse with Private Boat Rental: This holiday home rental outside of Crumpton offers an outdoor pool, a fireplace and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a patio, a garden and a selection of games so that you can immerse yourself in your holiday. See all 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 201 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 Skipjack Cove Yachting Resort 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.

Crumpton hotels from HK$553

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. Red Roof Inn & Suites Chestertown

3. Fairfield Inn & Suites by Marriott Middletown

4. Holiday Inn Express & Suites Middletown by IHG

5. Quality Inn Smyrna

6. Hampton Inn Middletown

7. Driftwood Inn

8. The Lodge at Great Oak Landing

9. Relax Inn Smyrna Dover Coastal Gateway

10. Inn at Huntingfield Creek

11. Haven Point Inn and Gallery

12. Bohemia Manor Farm

Stay near popular Crumpton attractions

Crumpton Park

Top Crumpton Hotel Reviews

Hampton Inn Middletown

The Lodge at Great Oak Landing

WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD

Exceptional River Front Family Retreat! - Dock, Private Beach & Bungalows

Serene Waterfront Cottage with dock and gorgeous views.

Red Roof Inn & Suites Chestertown

Haven Point Inn and Gallery

Relax Inn Smyrna Dover Coastal Gateway

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

More cheap stays in Crumpton

Red Roof Inn & Suites Chestertown

Quality Inn Smyrna

Holiday Inn Express & Suites Middletown by IHG

Relax Inn Smyrna Dover Coastal Gateway

Comfort Inn & Suites Chestertown

Hampton Inn Middletown

Frequently asked questions

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