Crumpton Holiday Rentals

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Our top choices for Crumpton holiday rentals

9.6 out of 10, Exceptional, (19)
"So pleased with all aspects of my stay. Clean, Comfortable, Quiet, Amenities all beyond expectation."
United States
Cynthia C.
The price is NZ$214
includes taxes & fees
31 Dec - 1 Jan 2026
Guest Suite for up to 2 in a Victorian on the Chester River
9.6 out of 10, Exceptional, (108)
"Amazing and neat and very private "
United States
Alexander M.
The price is NZ$272
includes taxes & fees
1 Jan - 2 Jan 2026
First Floor Studio Apartment in Historic Chestertown
9.8 out of 10, Exceptional, (8)
"The house is a beautiful place to stay. The location was ideal for going to attractions and stores. "
United States
Laurie S.
The price is NZ$608
includes taxes & fees
27 Dec - 28 Dec
Amazing Modern house with a full kitchen and parking
The price is NZ$713
includes taxes & fees
30 Dec - 31 Dec
Grandma’s Cottage will wrap around you like a warm hug
10.0 out of 10, Exceptional, (8)
"Such a great property. Second time coming and planning to come back next summer as well! Highly recommend! Amazing host!"
United States
Renee P.
The price is NZ$813
includes taxes & fees
13 Jan - 14 Jan 2026
HGTV quality, private guest suite, country getaway with hot tub & fire pit

Holiday Home in Kent County

High Tide Haven Suite
The price is NZ$342
includes taxes & fees
29 Dec - 30 Dec
High Tide Haven Suite
2.0 star property
The price is NZ$939
includes taxes & fees
5 Jan - 6 Jan 2026
Heated Pool • Private Backyard • Home Theater
10.0 out of 10, Exceptional, (25)
"If you’re looking for a relaxing scenic getaway as a couple or a family …this retreat is it! The views from the dock were amazing and it was very peaceful. The kids loved playing on the sandy beach area by the dock! We also explored some beach areas nearby. The place was beautiful and perfect for our family of 4! The hosts were great and very helpful!"
United States
Andrea M.
The price is NZ$533
includes taxes & fees
11 Jan - 12 Jan 2026
Waterfront Retreat with Private Dock and Beach

Holiday Home in Rock Hall

BAYSIDE BUNGALOW
10.0 out of 10, Exceptional, (52)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
The price is NZ$517
includes taxes & fees
1 Jan - 2 Jan 2026
BAYSIDE BUNGALOW

Holiday Home in Smyrna

JVA LUXURY HOUSING
10.0 out of 10, Exceptional, (1)
"The house was clean and wonderful. I highly recommend!"
United States
Daryl C.
The price is NZ$1,009
includes taxes & fees
1 Jan - 2 Jan 2026
JVA LUXURY HOUSING
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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Top Crumpton Hotel Reviews

Find out more about Crumpton

Everything you need to know about Crumpton holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Crumpton holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Crumpton holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Crumpton holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Crumpton. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Crumpton holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Crumpton holiday rentals we have selected for you start as low as NZ$272 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Crumpton rentals

At Expedia, we put the best Crumpton holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Crumpton rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Crumpton holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Crumpton. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

Frequently asked questions

Are there holiday rentals in Crumpton?

Yes, there are holiday rentals close to the most popular sights in Crumpton, or you can select a more secluded option if you're looking for a relaxing stay.

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

BAYSIDE BUNGALOW: This holiday home rental outside of Crumpton is equipped with a patio, air conditioning and WiFi to help you feel comfortable during your stay. Kitchen amenities include a fridge, a microwave and a coffee maker.

What’s there to see and do in Crumpton?

Explore the area and family-friendly sights such as Crumpton Auction, or get out into nature at a spot like Betterton Beach. In the wider area, you’ll find Rolphs Wharf Marina and Historical Society of Kent County Maryland.

What’s a holiday rental in Crumpton like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Crumpton. Holiday rentals offer amenities such as hot tubs, fire pits and patios so you'll be comfy for your stay. If you're concerned about a clean environment, a holiday rental can offer a sense of privacy away from public hotel lifts and busy concierge desks while still allowing you to travel. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is a great option for a family getaway.