Crumpton Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Tonight
4 Dec - 5 Dec
Tomorrow
5 Dec - 6 Dec
This weekend
5 Dec - 7 Dec
Next weekend
12 Dec - 14 Dec

Holiday Rentals in Crumpton

Exterior
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
9.6 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 HK$529
HK$974 total
includes taxes & fees
8 Dec - 9 Dec
Guest Suite for up to 2 in a Victorian on the Chester River
Property grounds
First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown

Chestertown
9.6 out of 10, Exceptional, (107)
"Amazing and neat and very private "
United States
Alexander M.
The price is HK$771
HK$1,236 total
includes taxes & fees
9 Dec - 10 Dec
First Floor Studio Apartment in Historic Chestertown
Dining
Amazing Modern house with a full kitchen and parking

Amazing Modern house with a full kitchen and parking

Smyrna
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 HK$1,401
HK$2,779 total
includes taxes & fees
10 Dec - 11 Dec
Amazing Modern house with a full kitchen and parking
Beach
Waterfront Retreat with Private Dock and Beach

Waterfront Retreat with Private Dock and Beach

Worton
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 HK$1,362
HK$2,449 total
includes taxes & fees
7 Dec - 8 Dec
Waterfront Retreat with Private Dock and Beach
Beach
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, (17)
"I loved the welcome basket! This place was extremely clean and had all the amenities that we needed. Much larger in person than even in the pictures. Walkable to town! "
United States
Tracy S.
The price is HK$917
HK$2,207 total
includes taxes & fees
6 Dec - 7 Dec
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Terrace/patio
HGTV quality, private guest suite, country getaway with hot tub & fire pit

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

Centreville
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 HK$1,534
HK$3,466 total
includes taxes & fees
17 Dec - 18 Dec
HGTV quality, private guest suite, country getaway with hot tub & fire pit
Terrace/patio
Grandma’s Cottage will wrap around you like a warm hug

Grandma’s Cottage will wrap around you like a warm hug

Betterton
The price is HK$1,751
HK$3,242 total
includes taxes & fees
1 Jan - 2 Jan 2026
Grandma’s Cottage will wrap around you like a warm hug
Terrace/patio
High Tide Haven Suite

High Tide Haven Suite

Kent County
The price is HK$1,348
HK$1,554 total
includes taxes & fees
7 Dec - 8 Dec
High Tide Haven Suite
A heated pool
Heated Pool • Private Backyard • Home Theater

Heated Pool • Private Backyard • Home Theater

2.0 star property
Middletown
The price is HK$1,572
HK$4,371 total
includes taxes & fees
22 Dec - 23 Dec
Heated Pool • Private Backyard • Home Theater
Outdoor dining
BAYSIDE BUNGALOW

BAYSIDE BUNGALOW

Rock Hall
10.0 out of 10, Exceptional, (52)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
The price is HK$1,557
HK$2,351 total
includes taxes & fees
1 Jan - 2 Jan 2026
BAYSIDE BUNGALOW
Outdoor dining
Chesapeake Bay Harbor View in a central location to events/restaurants

Chesapeake Bay Harbor View in a central location to events/restaurants

2.5 star property
Rock Hall
10.0 out of 10, Exceptional, (2)
"House was clean, great location. Furniture needs a little updating but overall our stay was great! Would definitely stay here again."
United States
Todd W.
The price is HK$1,751
HK$2,120 total
includes taxes & fees
5 Dec - 6 Dec
Chesapeake Bay Harbor View in a central location to events/restaurants
Private kitchen
JVA LUXURY HOUSING

JVA LUXURY HOUSING

Smyrna
10.0 out of 10, Exceptional, (1)
"The house was clean and wonderful. I highly recommend!"
United States
Daryl C.
The price is HK$3,113
HK$4,584 total
includes taxes & fees
11 Dec - 12 Dec
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Crumpton Hotel Reviews

Fairfield Inn & Suites by Marriott Middletown

Fairfield Inn & Suites by Marriott Middletown

10/10 Excellent
"Room was excellent; lobby was comforting; and stay was great!"
Maria 1-night trip
Posted 2 days ago
Fairfield Inn & Suites by Marriott Middletown

Find out more about Crumpton

Search for holiday rentals in Crumpton on Expedia! You can easily find your home rentals, villas, holiday apartments in Crumpton using one of the methods below:

  • View our selection of featured holiday rentals in Crumpton
  • Use the map to find apartments and other holiday homes in the Crumpton neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Crumpton while they last

Look no further and take a look at our great range of rental properties in Crumpton!

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?

Stunning Historic Downtown Home!! Within 2 Blocks of Fountain Park!!: This holiday home rental outside of Crumpton has air conditioning and laundry facilities to help you feel perfectly comfortable in your new surroundings.

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.