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Chestertown Hotel Guide - Crumpton Auction hotels in Chestertown, United States of America.

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Check prices for these dates

Tonight
15 Oct - 16 Oct
Tomorrow
16 Oct - 17 Oct
This weekend
16 Oct - 18 Oct
Next weekend
23 Oct - 25 Oct

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Our top choices for Crumpton Auction 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 brick wall with a sign stating "Washington College Founded 1782" and a tree above it.
A hotel room with two beds, a desk, a flat-screen TV, and a window with curtains.

1. Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
13.5 km from Crumpton Auction
United States
Amy
€97
includes taxes & fees
8 Nov - 9 Nov
Comfort Inn & Suites Chestertown
A hotel room with a sofa, two beds, a painting, and a lamp.
A hotel sign with a red background and white lettering, a parking lot, and a building with a brick facade.
A living room with a fireplace, a television, and a stone accent wall.
A hotel room with a bed, two bedside lamps, a sofa, a small table, and a painting on the wall.

2. Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
13.5 km from Crumpton Auction
United States
Kate
€71
includes taxes & fees
3 Nov - 4 Nov
Red Roof Inn & Suites Chestertown
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.

3. Driftwood Inn

Driftwood Inn
13.4 km from Crumpton Auction
United States
Kathy
€63
includes taxes & fees
16 Oct - 17 Oct
Driftwood Inn
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Hotels recommended for families near Crumpton Auction

A hotel room with a sofa, two beds, a painting, and a lamp.
A hotel sign with a red background and white lettering, a parking lot, and a building with a brick facade.
A living room with a fireplace, a television, and a stone accent wall.
A hotel room with a bed, two bedside lamps, a sofa, a small table, and a painting on the wall.

Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown
Chestertown
€71
includes taxes & fees
3 Nov - 4 Nov
Red Roof Inn & Suites Chestertown
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 brick wall with a sign stating "Washington College Founded 1782" and a tree above it.
A hotel room with two beds, a desk, a flat-screen TV, and a window with curtains.

Comfort Inn & Suites Chestertown

Comfort Inn & Suites Chestertown
Chestertown
€97
includes taxes & fees
8 Nov - 9 Nov
Comfort Inn & Suites Chestertown
A spacious living area with a dining table, sofa, and a kitchen in the background.
A modern kitchen with white cabinets, a central island, and pendant lighting.
A bedroom with a large bed, a nightstand, a lamp, a patterned rug, and a view through an open door to a hallway.
A modern kitchen with a large island, white cabinetry, and a view of the city.

Newly restored apartment in the heart of Chestertown

Newly restored apartment in the heart of Chestertown
Chestertown
€316
includes taxes & fees
18 Oct - 19 Oct
Newly restored apartment in the heart of Chestertown
A house with a swimming pool, surrounded by a fence, and two red umbrellas.
A closet with a wooden floor, a white door, and a blue bag on top.
A building with a balcony and large windows, surrounded by trees and a fence.
A bedroom with a bed, a ceiling fan, a painting, and a door leading to another room.

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
€146
includes taxes & fees
19 Oct - 20 Oct
First Floor Studio Apartment in Historic Chestertown
A kitchen with wooden cabinets, a dining table, and a refrigerator.
A cozy dining room with a wooden table and chairs, surrounded by bookshelves and a fireplace.
A piano in a room with wooden flooring and a chair with a floral pattern.
A two-story brick building with a symmetrical facade, a central entrance, and a well-maintained lawn.

Family Retreat at Lansdowne Manor

Family Retreat at Lansdowne Manor
Centreville
Family Retreat at Lansdowne Manor
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 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.

The Lodge at Great Oak Landing

The Lodge at Great Oak Landing
Chestertown
€110
includes taxes & fees
28 Oct - 29 Oct
The Lodge at Great Oak Landing
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 modern restaurant with a long counter, multiple seating areas, and pendant lighting.
A modern living room with a stone fireplace, wooden ceiling, and a large TV mounted above it.

Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown
Middletown
€118
includes taxes & fees
1 Nov - 2 Nov
Fairfield Inn & Suites by Marriott Middletown
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 reception desk with a sign reading "Quality Inn" and a potted plant beside it.
A hotel room with two beds, a TV, a desk, and a window with curtains.

Quality Inn Smyrna

Quality Inn Smyrna
Smyrna
€93
includes taxes & fees
25 Oct - 26 Oct
Quality Inn Smyrna

Top Crumpton Auction Hotel Reviews

Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown

8/10 Good
"Hotel was great. Really nice. loved having doormen considering area is not great. Just wished"
Lisa 1-night trip
Posted 1 day ago
Fairfield Inn & Suites by Marriott Middletown
Holiday Inn Express & Suites Middletown by IHG

Holiday Inn Express & Suites Middletown by IHG

8/10 Good
"Friendly staff. Breakfast was adequate. Parking was close."
Charles 1-night trip
Posted 1 day ago
Holiday Inn Express & Suites Middletown by IHG
Red Roof Inn & Suites Dover Downtown

Red Roof Inn & Suites Dover Downtown

10/10 Excellent
"Great. Just an overnight stay"
Ronald 1-night trip
Posted 2 days ago
Red Roof Inn & Suites Dover Downtown
Sleep Inn & Suites Dover University Area

Sleep Inn & Suites Dover University Area

8/10 Good
"Room card did not work, we had to go to the front desk every time that we need to get into the room, because the card did not work at the room door."
Daryl 2-night trip
Posted 2 days ago
Sleep Inn & Suites Dover University Area
Relax Inn Smyrna Dover Coastal Gateway

Relax Inn Smyrna Dover Coastal Gateway

8/10 Good
"The area felt safe, the front desk guy was very kind. The room wasn’t in amazing condition but wasn’t terrible"
Kristen 1-night trip
Posted 10 days ago
Relax Inn Smyrna Dover Coastal Gateway
Hampton Inn Middletown

Hampton Inn Middletown

10/10 Excellent
"The male employee working night shift hours on 10/03/2026 was more than accommodating and polite."
Heather 1-night trip
Posted 11 days ago
Hampton Inn Middletown
Hampton Inn Dover

Hampton Inn Dover

10/10 Excellent
"nice"
Dawn 4-night trip
Posted 2 weeks ago
Hampton Inn Dover
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

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."
JoAnn W. 4-night trip
Posted 2 months ago
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

Other attractions near Crumpton Auction

Crumpton Park

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

Pinkney Park

Explore the great outdoors at Pinkney Park, a lovely green space in Millington.
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Chase Island

Commune with nature and explore the great outdoors at Chase Island during your travels in Chestertown. Experience the area's festivals and art scene.
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Roundtop Park

Roundtop Park is just one of the places to see in Chestertown, so why not enjoy the other things to explore during your travels? Experience the area's festivals and art scene.
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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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Rolphs Wharf Marina

8.2/10 (15 reviews)
Explore the waterfront in Chestertown with a trip to Rolphs Wharf Marina. Take in the festivals in this family-friendly area.
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Frequently asked questions

What's the area like around Crumpton Auction?
Crumpton Auction is located in an area of Chestertown that travellers like for its university setting. You'll find 13 hotels and other accommodations within a few miles for a convenient home base.
What's the best hotel to stay near Crumpton Auction?
Red Roof Inn & Suites Chestertown is one of the top choices for your stay based on our traveller data, and this hotel offers free parking and free WiFi. You'll find it 8.4 mi (13.5 km) from Crumpton Auction. Other good choices in the area include Comfort Inn & Suites Chestertown and The Lodge at Great Oak Landing.
How many hotels will I find near Crumpton Auction?
Expedia has 13 hotels and other accommodation options a few miles from Crumpton Auction.
If I need to cancel the hotel reservation for my stay near Crumpton Auction, will I receive a refund?
Yes! Most hotel bookings are refundable provided that you cancel before the accommodation's cancellation deadline, which often is within 24-48 hours of check in. If you booked a non-refundable reservation, it may still be possible to cancel it and be given a refund within a 24-hour period of your booking. Add dates, click "Search", then use the filter option "fully refundable" to review the best options available near Crumpton Auction.