Holiday Rentals Crumpton from £120: Find Short-Term Rentals & Holiday Accommodations

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Our top choices for Crumpton holiday rentals

A two-story house with a gabled roof, a front porch, and a front door with a decorative surround.

1. Guest Suite for up to 2 in a Victorian on the Chester River

Millington

Riley B.

includes taxes & fees

14 Sept - 15 Sept

A house with a swimming pool, surrounded by a fence, and two red umbrellas.

2. First Floor Studio Apartment in Historic Chestertown

Chestertown

S G.

includes taxes & fees

2 Sept - 3 Sept

3. Cozy 1-bedroom in-law suite in lovely Chestertown with AC

Chestertown

includes taxes & fees

8 Sept - 9 Sept

4. Studio Apartment 5 Miles from Dover in quiet town of Hartly w/Dollar Store

Hartly

includes taxes & fees

2 Sept - 3 Sept

5. Secluded Cottage in Middle of Chestertown

Chestertown

Amy D.

includes taxes & fees

2 Sept - 3 Sept

A spacious living area with a dining table, sofa, and a kitchen in the background.

6. Newly restored apartment in the heart of Chestertown

Chestertown

Anonymous traveller

includes taxes & fees

2 Sept - 3 Sept

A park with a curved wooden bridge, a tree with purple blossoms, and a grassy area.

7. Wren Retweet- Country Estate in Center of C’Town

Chestertown

Mandy D.

includes taxes & fees

8 Sept - 9 Sept

A covered porch with a wooden floor, a sofa with cushions, a ceiling fan, and a view of a green landscape.

8. Beachcomber Suite

Kent County

"We absolutely loved staying at the Beachcomber Suite. Tucked away off the main road, with a massive screened porch to enjoy the country side and gardens. It was cosy, clean, well appointed. The shower was amazing. We had a multi-course dinner at Sassafras on the water which was right up the road, 3 minutes away on the water front. I got a text from Jane and Dennis that evening if I wanted fresh bagels in the morning. Well, of course I do! They were warm multi seed and fantastic start to...

Lisa E.

includes taxes & fees

21 Sept - 22 Sept

A bedroom with a wooden headboard, striped pillows, a turtle-shaped pillow, and wall-mounted lamps.

9. Turtle Cove Room

Kent County

includes taxes & fees

21 Sept - 22 Sept

A sandy beach with a wooden walkway leading to a calm lake, surrounded by dense green foliage.

10. Waterfront Retreat with Private Dock and Beach

Worton

Max G.

includes taxes & fees

2 Sept - 3 Sept

A gazebo on a sandy beach with a clear view of the ocean and rocky shoreline.

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

Rock Hall

lisa p.

includes taxes & fees

2 Sept - 3 Sept

A brick house with a front porch, a chimney, and a well-maintained lawn.

12. Bohemia Manor Farm

Chesapeake City

includes taxes & fees

8 Sept - 9 Sept

A building with a gabled roof and a circular vent on the roof.

13. BAYSIDE BUNGALOW

Rock Hall

Diane V.

includes taxes & fees

15 Sept - 16 Sept

A two-story brick building with a symmetrical facade, a central entrance, and a well-maintained lawn.

14. Family Retreat at Lansdowne Manor

Centreville

Emily C.

includes taxes & fees

23 Sept - 24 Sept

A spacious living room with a leather sofa, a wooden coffee table, and a fireplace.

15. Bayside Cottage steps from Rock Hall Harbor

Rock Hall

Adam S.

includes taxes & fees

29 Sept - 30 Sept

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Top Crumpton Hotel Reviews

Comfort Inn & Suites Chestertown

8/10 Good

"good stay"

The Lodge at Great Oak Landing

10/10 Excellent

"Gem of a local place on the water. The rooms are big and the beds are soooo comfy. The pool is cute and the beach has bands on weekends. There are gas grills and a decent restaurant. It's not fancy (for fancy stay at the manor next door). But it's not corporate either. It's authentic, peaceful and fun."

Inn at Huntingfield Creek

10/10 Excellent

"The property was stunning. The rooms were very comfortable and the bathroom had all you need. We also really appreciated the drinks and free salted chocolate chip cookies. They were delicious. The inn keepers were and their dogs were a highlight for us. The breakfast was also absolutely delicious. Definitely would recommend this I"

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 £120 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?

Welcome to Bayside Breeze! One Block From Town Beach, Walk to Waterfront Dining: This holiday home rental outside of Crumpton is located near the beach, and has a patio, a selection of games and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop.

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 Turner's Creek Park. 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.

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Check prices for these dates

Our top choices for Crumpton holiday rentals

1. Guest Suite for up to 2 in a Victorian on the Chester River

2. First Floor Studio Apartment in Historic Chestertown

3. Cozy 1-bedroom in-law suite in lovely Chestertown with AC

4. Studio Apartment 5 Miles from Dover in quiet town of Hartly w/Dollar Store

5. Secluded Cottage in Middle of Chestertown

6. Newly restored apartment in the heart of Chestertown