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Check Crumpton hotel prices

Tonight
23 Nov - 24 Nov
Tomorrow night
24 Nov - 25 Nov
Next weekend
29 Nov - 1 Dec

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Top hotels and accommodation in Crumpton

The Lodge at Great Oak Landing
Private beach nearby, sun-loungers, beach volleyball

The Lodge at Great Oak Landing

3.5 star property
7.6 out of 10, Good, (45)
"Generally okay, Clean but property could use some upgrade"
The price is AU$171
includes taxes & fees
2 Dec - 3 Dec
The Lodge at Great Oak Landing
Comfort Inn & Suites Chestertown
Lobby

Comfort Inn & Suites Chestertown

2.5 star property
8.6 out of 10, Excellent, (727)
"Was there just one night and didn't eat breakfast, but staff were wonderful and the room seemed newly renovated. Room was large and clean with coffee maker and mini-fridge. "
The price is AU$182
includes taxes & fees
15 Dec - 16 Dec
Comfort Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
Suite, Multiple Beds, Non Smoking

Red Roof Inn & Suites Chestertown

2.0 star property
7.2 out of 10, Good, (320)
"Comfortable room and fair price for the room size. Very clean. Bathroom was nice but had a broken wall mounted hair dryer and the bathroom door did not latch closed so it stayed open about an inch. Front desk was businesslike but not the least bit friendly. There is no breakfast or even coffee offered. You have to go out for breakfast. Excuse was not since Covid. That adds another $20 per couple for breakfast to the room price."
The price is AU$127
includes taxes & fees
16 Dec - 17 Dec
Red Roof Inn & Suites Chestertown
Driftwood Inn
Lobby

Driftwood Inn

2.0 star property
5.0 out of 10, (167)
"Rooms were clean. Check-in was a breeze, and the housekeeping lady is the best left her a nice tip"
The price is AU$108
includes taxes & fees
2 Dec - 3 Dec
Driftwood Inn
Inn at Huntingfield Creek
Lake

Inn at Huntingfield Creek

3.5 star property
10.0 out of 10, Exceptional, (48)
"This place was awesome. My wife and I stayed here during their slower season. My wife and I got our cottage room upgraded free of charge. The staff was extremely friendly and the supply of alcohol is a great touch! The property is huge and the three dogs on the property are very good at their job and very friendly. Honestly I have zero complaints. The tv wiring had crossed wires with the fireplace or something because the volume would turn off the fireplace as well, but that was such a minor...
The price is AU$334
includes taxes & fees
1 Dec - 2 Dec
Inn at Huntingfield Creek
Mariners Motel
Outdoor pool

Mariners Motel

2.0 star property
9.4 out of 10, Exceptional, (88)
"Great location and very well cared for older motel. Updating extremely well done. We enjoyed the complimentary bikes, being so close to the water and the many good restaurants nearby. We will be back!"
The price is AU$245
includes taxes & fees
1 Dec - 2 Dec
Mariners Motel
First Floor Studio Apartment in Historic Chestertown
Property grounds

First Floor Studio Apartment in Historic Chestertown

9.6 out of 10, Exceptional, (75)
"EasyvPeasy place."
The price is AU$246
includes taxes & fees
27 Nov - 28 Nov
First Floor Studio Apartment in Historic Chestertown
BAYSIDE BUNGALOW
Exterior detail

BAYSIDE BUNGALOW

10.0 out of 10, Exceptional, (33)
"The bay cottage's porch was a perfect spot to enjoy a bottle of wine and snacks provided by the thoughtful hosts. Clever decor , furnishings, and sauna made our stay special and warm. Had crab dinner viewing sunset over the bay at dockside suggested by hosts. we hope to return. "
The price is AU$418
includes taxes & fees
24 Nov - 25 Nov
BAYSIDE BUNGALOW
Waterfront Retreat with Private Dock and Beach
Miscellaneous

Waterfront Retreat with Private Dock and Beach

10.0 out of 10, Exceptional, (17)
"This property was exactly what we needed! The apartment was very clean and well maintained making it such a pleasant experience. Even though the property is shared with the owners, they weren’t constantly around or hovering over us allowing us to enjoy our time together. We loved having the dock and availability of the kayaks so we didn’t have to bring us along for the long trip there. We found some small shops and cute little towns along with a wonderful winery all within a short drive from...
The price is AU$485
includes taxes & fees
1 Dec - 2 Dec
Waterfront Retreat with Private Dock and Beach
Bayside Cottage steps from Rock Hall Harbor
Fridge, microwave, oven, stovetop

Bayside Cottage steps from Rock Hall Harbor

10.0 out of 10, Exceptional, (2)
"Thank you - towels hanging bathroom. Outside trash can was full when we got there. We took our trash with us. thank you - MBVK"
Bayside Cottage steps from Rock Hall Harbor
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Miscellaneous

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

10.0 out of 10, Exceptional, (4)
"A great place to chill out and enjoy what Rock Hall has to offer. It’s always great to come back to my childhood town. Rick is a great host and takes really good care of the property! We will be back."
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
Interior

Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna

10.0 out of 10, Exceptional, (31)
"We had my daughter's wedding at this beautiful villa. The views were absolutely amazing! The house is very spacious and accommodated our family. The sunsets were spectacular. Everyone enjoyed the pool, hot tub, and all the other activities this house had to offer"
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
Circa 1900 Home in the Heart of Historic Downtown Chestertown
Fridge, microwave, oven, stovetop

Circa 1900 Home in the Heart of Historic Downtown Chestertown

10.0 out of 10, Exceptional, (64)
"We enjoyed everything about the property."
Circa 1900 Home in the Heart of Historic Downtown Chestertown
River Cottage, Chestertown
Fridge, microwave, oven, stovetop

River Cottage, Chestertown

2.0 star property
River Cottage, Chestertown
Cottage with Harbor and Chesapeake Bay View in Rock Hall, MD
Beach towels

Cottage with Harbor and Chesapeake Bay View in Rock Hall, MD

9.8 out of 10, Exceptional, (60)
"Great place near the marina. Kitchen was well equipped for cooking our own meals. Nice recent updates to the bathroom and kitchen. Covered porch out back is also quite nice. We enjoyed our stay and would gladly return to this house!"
Cottage with Harbor and Chesapeake Bay View in Rock Hall, MD
Serene Waterfront Cottage with dock and gorgeous views.
Fridge, microwave, dishwasher, coffee/tea maker

Serene Waterfront Cottage with dock and gorgeous views.

9.6 out of 10, Exceptional, (37)
"Love this place. It was perfect for us. Rooms are spacious. "
Serene Waterfront Cottage with dock and gorgeous views.
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
Beach nearby, sun-loungers, beach towels

Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach

9.6 out of 10, Exceptional, (35)
"This house had the most amazing views and was clean and tidy. It was perfect for us and the dogs. The yard was clean and mowed and provided plenty of room for frisbee play which is part of my german shepherd's job. The kitchen was very adequate for our needs! As expected, the upstairs bedrooms were "historic" and the staircase was steep also "historic". The showers were perfect. We had a great visit and would love to come back here!"
Historic Waterfront Home with Chesapeake Bay View. Sleeps 9. Close to the Beach
Peaceful getaway convenient to local amenities including beach, boating & food
Beach towels

Peaceful getaway convenient to local amenities including beach, boating & food

9.8 out of 10, Exceptional, (109)
"We were in town for the local triathlon and had a great stay! My kids (3&4) and I were able to walk to the finish line from the location. The house was clean and large enough that we were all comfortable. If you have kids, it’s across the street from a cool boat playground. Diane was very responsive to my questions and provided plenty of towels, blankets, etc. Overall, a great stay! "
Peaceful getaway convenient to local amenities including beach, boating & food
RELAXING, SWIMMING, WALKING, KAYAKING, HIKING, FISHING & DINING
Beach nearby, sun-loungers, beach towels

RELAXING, SWIMMING, WALKING, KAYAKING, HIKING, FISHING & DINING

7.4 out of 10, Good, (3)
"About a 10 minute walk to main street, 15-20 to the Marinas. The house is cute, has a nice common room, and the bed was comfy."
RELAXING, SWIMMING, WALKING, KAYAKING, HIKING, FISHING & DINING
Oyster Cottage - walk to shops , Mainstay music venue and the Bay!
Property grounds

Oyster Cottage - walk to shops , Mainstay music venue and the Bay!

10.0 out of 10, Exceptional, (5)
"My friend and I wanted to meet up part way between our two cities, and when we decided on the Chesapeake Bay, Rock Hall seemed a good option, and we were right! What a great little town, and the house was just perfect for us. She brought her two little ones (6 and 2), and I was on my own. I think with just 1 bathroom, many more than that would really not be ideal. The whole stay was great, we both agreed we'd love to come back again. The only hiccup (and I am sure it will be fixed), was that...
Oyster Cottage - walk to shops , Mainstay music venue and the Bay!
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.
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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 Hampton Inn Middletown and Holiday Inn Express And Suites Middletown, an IHG Hotel. See all available top hotels, or vacation rentals in Crumpton.

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

Waterfront w/private pier located near Rock Hall, REMODEDLED and ENLARGED for 16: This holiday home rental outside of Crumpton is located on the waterfront, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Make the most of an arcade/games room in this rental home to help you unwind. 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 are some accommodation options with pools in Crumpton?

Holiday Inn Express And Suites Middletown, an IHG Hotel: Features free buffet breakfast, a pool and free Internet. Hampton Inn Middletown and Inn at Huntingfield Creek are a couple of other choices with an on-site pool. View all hotels with pools in Crumpton.

What is staying in Crumpton like?

Travellers to Crumpton will find plenty to explore and enjoy. There are 171 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 Rolphs Wharf Marina, Betterton Beach and Elk Neck State Park. You'll also find Tilmon's Island Winery and Crow Farm and Vineyard 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.