Crumpton Holiday Rentals from €141: Search Short-Term Rentals

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Holiday Rentals in Crumpton

Kitchen area with a stove, dishwasher, refrigerator, sink, and countertop with a kettle.

"My family and I had a ball, enjoyed our time on the water and hanging out on the farm. "

Stroll through the serene garden, surrounded by lush plants and a majestic tree.

"Lovely place to stay in downtown Chestertown. So close to walk to eating, shopping and events. Had many great amenities to make the stay comfortable. Host was very communicative and quick to respond. "

"Wonderful quiet night in Rock Hall. Quick walk to Blue Heron Oyster for dinner. "

includes taxes & fees

18 Aug - 19 Aug

Enjoy a serene beach experience with access to the ocean via the public pier.

"This is a jewel as it is private, peaceful with lovely setting."

Enjoy a meal with a view of the ocean from this dining area with large windows.

"Relaxing and stunning location. Beautiful bay front property with stunning views of the bay. If you are looking for a quiet and peaceful getaway that involves wildlife sightings this is the perfect spot. Well equipped and roomy rental. Very clean too. "

Enjoy cooking in this well-equipped kitchen with a central island, stainless steel appliances, and a granite countertop.

"a great place to unwind. "

Enjoy a meal with a view from the kitchen's glass doors, which lead to a patio with a deck and seating area overlooking a serene landscape.

"Great location with a great view."

Relax in this stylish living room with a large sofa, armchair, and ottoman, perfect for unwinding in comfort.

"Lovely cottage, well-equipped, immaculately clean. "

Enjoy meals at the central island with a round table and two chairs in this well-equipped kitchen.

"Property is beautiful, host answered our questions in a timely manner. Would stay again "

Enjoy a serene beach experience with a gentle shoreline and peaceful surroundings.

"This house was the cutest little place right across the street from the beach with a beautiful view. The house was clean and had all the amenities needed for our stay. We would definitely stay there again!"

Enjoy a leisurely game of pool or foosball in this spacious indoor recreation area with a pool table and foosball table.

"Overall, our stay was fantastic. The weather was absolutely magnificent the entire stay."

Relax in this inviting living space with a comfortable sofa, a cozy bed, and a peaceful atmosphere.

"Had a very comfortable stay here. Very clean and the towels to kill for (ha). Ms. Lynn kept in touch at all times. I would stay here again for sure."

Relax by the pool surrounded by a tranquil golf course view.

"Very pretty location. Few minutes drive to town center."

includes taxes & fees

13 Aug - 14 Aug

Stroll through the beautifully manicured lawn to the charming entrance, flanked by a picket fence and a garage with a covered porch.

"Extremely clean, comfortable, and cozy place to stay for a weekend trip. The host was great to work with. We would definitely stay again."

Simple, two-story building with a flat roof, surrounded by trees in a tranquil setting.

"The house is roomy and was clean and well stocked."

Enjoy cooking in this well-equipped kitchen with a central island and bench, featuring stainless steel appliances and ample cabinetry.

"This property was perfect for our trip. It was very clean, comfortable and feels like home. Description and photos on the website were accurate. The owners were very attentive and hospitable. This is definite a place I’ll return to."

Enjoy cooking in this well-equipped kitchen with a large island and modern appliances.

"Nice place with everything I could want. Would stay there again!"

Escape to a charming cottage surrounded by lush greenery and trees, with a cozy porch and a brick chimney.

"Beautiful location on the river. We were visiting family in the fall so did not use the kayaks available—maybe next time! Nice to have a dog-friendly place too. Great and prompt communication with the hosts."

Relax in a serene hot tub under a covered pergola with a breathtaking view of the surrounding landscape.

"Was looking for an upscale beautiful place to stay for a family wedding. Found it! Tammy has tended to every detail at this VRBO. Gorgeous farmhouse chic. Very attentive to our texts. And always good to return to Centreville to see friends and family. "

includes taxes & fees

20 Aug - 21 Aug

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Top Crumpton Hotel Reviews

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

10/10 Excellent

"My husband and I were there for our anniversary weekend. Hosts were very friendly, had good recommendations, and place was modern and clean! We enjoyed the beach area, sunsets and walks in the neighborhood. We brought our own kayaks and fished... caught lots of catfish!! We brought our bikes for Chesapeake City.We enjoyed the Bohemia Manor Winery nearby. Great sunsets and great memories! Thanks again! "

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

10/10 Excellent

"Wonderful location for a quiet extended-family stay. Lots of room for everyone across our four generations. We like to cook, and the huge dining table was perfect for being together for meals. Excellent seafood nearby. We brought our kayaks and went up & downriver, and bicycles for rides alongside the canal. Golfed at two nearby courses & had a great time overall! Owner (Dennis) was very responsive and friendly. Gorgeous view and lovely sunsets. Thanks!"

Serene Waterfront Cottage with dock and gorgeous views.

10/10 Excellent

"Very clean and comfortable, perfect for a getaway for a couple or small family. Even though the neighbors are close, the house and dock feel very private and the views are breathtaking. The property manager communicated quickly and the guest guide that was provided was so detailed and helpful. Very tasty restaurants nearby. I would absolutely return. Next time I'd love to try out the boats!"

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, apart-hotels, 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 €141 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?

Amazing Waterfront house with expansive views of the Chesapeake Bay and Sunsets: This holiday home rental outside of Crumpton is equipped with a patio, air conditioning and laundry facilities to help you feel comfortable during your stay. It has 4 bedrooms, as well as a kitchen with a dishwasher, a microwave and a coffee maker, so that you can cook with friends or family.

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 Chestertown Dog Park. In the wider area, you’ll find Tilmon's Island Winery and Church Hill Theatre.

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.

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Holiday Rentals in Crumpton

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Holiday Rentals in Crumpton

Secluded Waterfront Cottage on 200 acre farm near Queenstown

Historic Downtown Garden Oasis with Private Patio

BAYSIDE BUNGALOW

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

Amazing Waterfront house with expansive views of the Chesapeake Bay and Sunsets

Lark's Nest on the Chester River. Spacious, waterfront home with private dock.

Waterfront w/private pier, pool, Hot Tub, kayaks and in town.

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

Spacious and luxurious 3 bed/1.5 bath townhome with free parking, sleeps 6

Eastern Shore beach cottage get-away

Charming, updated 1930's beachfront cottage with stunning sunset views

Waterfront Estate w Private Pier, Game Room & Bar

The She Shed a Cozy Country Setting to relax! 15 min to Dover, DE

First Floor Studio Apartment in Historic Chestertown

Peaceful Retreat on the Eastern Shore. Nature lover’s paradise!

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

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

Serene Waterfront Cottage with dock and gorgeous views.

Chester River Waterfront, Magnificent Views, Dock, Beach, close 2 town

HGTV quality, private guest suite, country getaway with hot tub & fire pit

Top Crumpton Hotel Reviews

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

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

Red Roof Inn & Suites Chestertown

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

Holiday Inn Express And Suites Middletown by IHG

The Lodge at Great Oak Landing

Hampton Inn Middletown

Secluded Waterfront Cottage on 200 acre farm near Queenstown

Serene Waterfront Cottage with dock and gorgeous views.

Find out more about Crumpton

Frequently asked questions