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Crumpton Holiday Rentals

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Check prices for these dates

In two weeks
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

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

Guest Suite for up to 2 in a Victorian on the Chester River
Millington
9.8 out of 10, Exceptional, (30 reviews)
"Convenient, clean, super friendly host, loved it. Highly recommend!!!"
United States
Quinton
The price is AU$181
includes taxes & fees
22 Oct - 23 Oct
Guest Suite for up to 2 in a Victorian on the Chester River
A house with a swimming pool, surrounded by a fence, and two red umbrellas.

2. First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.8 out of 10, Exceptional, (130 reviews)
"A beautiful and comfortable accomodations."
United States
John R.
The price is AU$229
includes taxes & fees
22 Oct - 23 Oct
First Floor Studio Apartment in Historic Chestertown
A living room with a fireplace, patterned furniture, a coffee table, and a bookshelf.

3. Secluded Cottage in Middle of Chestertown

Secluded Cottage in Middle of Chestertown
Chestertown
10.0 out of 10, Exceptional, (2 reviews)
"Robert and Elizabeth were great hosts. They are very communicative and flexible. The house itself is lovely, with nicely decorated rooms and so spacious! The location can’t be beat. Will definitely stay here again."
United States
Amy D.
The price is AU$394
includes taxes & fees
25 Oct - 26 Oct
Secluded Cottage in Middle of Chestertown
A shower with a handheld showerhead and a wall-mounted faucet.

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

Cozy 1-bedroom in-law suite in lovely Chestertown with AC
Chestertown
8.0 out of 10, Very good, (1 review)
"Our first using VRBO. We were not sure what to expect but hoped it was as true as the listing. The home was cleaned and very nicely decorated. The bed was very comfortable and the home was spacious for two worked great. The water pressure was also great. Some small improvements will definitely give this place a 5 star. There was no closet to hang a men’s jacket or sun dresses; no mirror except in the bathroom and perhaps some coasters would help when spending some time reading in the living...
United States
Miriam G.
The price is AU$408
includes taxes & fees
27 Oct - 28 Oct
Cozy 1-bedroom in-law suite in lovely Chestertown with AC
A covered porch with a wooden floor, a sofa with cushions, a ceiling fan, and a view of a green landscape.

5. Beachcomber Suite

Beachcomber Suite
Kent County
10.0 out of 10, Exceptional, (1 review)
"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...
United States
Lisa E.
The price is AU$309
includes taxes & fees
26 Oct - 27 Oct
Beachcomber Suite
A bedroom with a wooden headboard, striped pillows, a turtle-shaped pillow, and wall-mounted lamps.

6. Turtle Cove Room

Turtle Cove Room
Kent County
The price is AU$287
includes taxes & fees
26 Oct - 27 Oct
Turtle Cove Room
A spacious living area with a dining table, sofa, and a kitchen in the background.

7. Newly restored apartment in the heart of Chestertown

Newly restored apartment in the heart of Chestertown
Chestertown
10.0 out of 10, Exceptional, (34 reviews)
"Enjoyable stay. All was as advertised. The host was very helpful when asked for information. Location was wonderful, very central in the old part of town. We had a great time!"
United States
Susan A.
The price is AU$488
includes taxes & fees
22 Oct - 23 Oct
Newly restored apartment in the heart of Chestertown
A house with a blue front door, two windows, and a small porch.

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

Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Rock Hall
10.0 out of 10, Exceptional, (30 reviews)
"Great property! Great accommodations! Wonderful host"
United States
lisa p.
The price is AU$417
includes taxes & fees
26 Oct - 27 Oct
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
A hotel layout with multiple bedrooms, a bathroom, a kitchen, and a living area.

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

Wren Retweet- Country Estate in Center of C’Town
Chestertown
10.0 out of 10, Exceptional, (75 reviews)
"Perfect location for exploring the cutest town. "
United States
Mandy D.
The price is AU$665
includes taxes & fees
2 Nov - 3 Nov
Wren Retweet- Country Estate in Center of C’Town
A building with a gabled roof and a circular vent on the roof.

10. BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (67 reviews)
"Perfect little place for our weekend stay!"
United States
Diane V.
The price is AU$436
includes taxes & fees
22 Oct - 23 Oct
BAYSIDE BUNGALOW
A brick house with a front porch, a chimney, and a well-maintained lawn.

11. Bohemia Manor Farm

Bohemia Manor Farm
3.5 star property
Chesapeake City
8.0 out of 10, Very good, (1 review)
The price is AU$467
includes taxes & fees
28 Oct - 29 Oct
Bohemia Manor Farm
A single-story house with a front porch, surrounded by a well-maintained lawn and trees.

12. Cozy Family Friendly 1 story 3-bedroom house in charming Betterton

Cozy Family Friendly 1 story 3-bedroom house in charming Betterton
Betterton
The price is AU$491
includes taxes & fees
26 Oct - 27 Oct
Cozy Family Friendly 1 story 3-bedroom house in charming Betterton
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

Holiday Inn Express & Suites Middletown by IHG

Holiday Inn Express & Suites Middletown by IHG

10/10 Excellent
"Friendly staff"
Jennifer 1-night trip
Posted 2 days ago
Holiday Inn Express & Suites Middletown by IHG

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 favourite 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 depend 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 AU$229 per night. Entering your travel dates in the search wizard might find you 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?

The Colonial Farmhouse with Private Boat Rental: This holiday home rental outside of Crumpton offers an outdoor pool, a fireplace and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a patio, a garden and a selection of games so that you can immerse yourself in your holiday.

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 Crow Farm and Vineyard and Rolphs Wharf Marina.

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.