Crumpton Vacation Rentals

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Apr 24 - Apr 26
In two months
Jun 5 - Jun 7
In three months
Jul 3 - Jul 5
In four months
Jul 31 - Aug 2

Our top choices for Crumpton vacation rentals

Property grounds

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (108 reviews)
"Every thing was great"
United States
lesia k.
$144 nightly
The price is $159
Apr 15 - Apr 16
Total with taxes and fees
First Floor Studio Apartment in Historic Chestertown
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, (20 reviews)
"So pleased with all aspects of my stay. Clean, Comfortable, Quiet, Amenities all beyond expectation."
United States
Cynthia C.
$118 nightly
The price is $125
Apr 13 - Apr 14
Total with taxes and fees
Guest Suite for up to 2 in a Victorian on the Chester River
Terrace/patio

Amazing Modern house with a full kitchen and parking

Amazing Modern house with a full kitchen and parking
Smyrna
9.2 out of 10, Wonderful, (10 reviews)
"The house is a beautiful place to stay. The location was ideal for going to attractions and stores. "
United States
Laurie S.
$299 nightly
The price is $306
Apr 15 - Apr 16
Total with taxes and fees
Amazing Modern house with a full kitchen and parking
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, (18 reviews)
"Close to Main Street. Very nice and spacious accommodations."
United States
Michael D.
$255 nightly
The price is $281
Apr 13 - Apr 14
Total with taxes and fees
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!
Smart TV

Bayside Cottage steps from Rock Hall Harbor

Bayside Cottage steps from Rock Hall Harbor
Rock Hall
10.0 out of 10, Exceptional, (2 reviews)
"Property was nicely refurbished and furnished and well equipped. The younger set especially enjoyed the 5 bikes in good condition and the large yard to play sports. All in all, a great weekend stay!"
United States
Dorothy R.
$343 nightly
The price is $364
Apr 13 - Apr 14
Total with taxes and fees
Bayside Cottage steps from Rock Hall Harbor
Terrace/patio

High Tide Haven Suite

High Tide Haven Suite
Kent County
10.0 out of 10, Exceptional, (1 review)
"The suite was really nice and extremely clean. Comfy, memory foam bed. Excellent shower with great water pressure. The ambiance in the room is serene and beachy making for a wonderful escape. Absolutely loved their screened in porch and view from the back deck. The hosts were very nice, had great communication and served the most delicious bagels. We left our phone charger there and they promptly called us in time to turn around and get it. Highly recommend this location and will stay there...
United States
Joell V.
$151 nightly
The price is $164
Apr 20 - Apr 21
Total with taxes and fees
High Tide Haven Suite
Exterior detail

BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (52 reviews)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
$260 nightly
The price is $276
Apr 30 - May 1
Total with taxes and fees
BAYSIDE BUNGALOW
Beach

Waterfront Retreat with Private Dock and Beach

Waterfront Retreat with Private Dock and Beach
Worton
10.0 out of 10, Exceptional, (25 reviews)
"The apartment, including kitchen and bathroom, was very clean. Plenty of linens available for use. Perfect spot for fishing off of their dock. Very pleased with our reservation. "
United States
Debbie S.
$343 nightly
The price is $379
May 6 - May 7
Total with taxes and fees
Waterfront Retreat with Private Dock and Beach
Dining

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

Grandma’s Cottage will wrap around you like a warm hug
Betterton
$400 nightly
The price is $424
Apr 18 - Apr 19
Total with taxes and fees
Grandma’s Cottage will wrap around you like a warm hug
Interior

JVA LUXURY HOUSING

JVA LUXURY HOUSING
Smyrna
10.0 out of 10, Exceptional, (1 review)
"The house was clean and wonderful. I highly recommend!"
United States
Daryl C.
$564 nightly
The price is $582
Apr 19 - Apr 20
Total with taxes and fees
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

Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

6/10 Okay
"Its OK considering the inexpensive cost per night. The room was clean with the exceprion of a dead wasp under the bathroom vanity. Lobby staff was professional when we checked in, although not a particularly happy greeting...note: a smile and a "Hello" instead of just a straight faced "Checking in?" greeting goes a long way towards good customer "first impressions". Room amenities are minimal but adequate for a night. Overall, its OK."
Michael 1-night trip
Posted 3 hours ago
Red Roof Inn & Suites Chestertown

Find out more about Crumpton

Everything you need to know about Crumpton vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Crumpton vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Crumpton vacation 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 low season months. For more hustle and bustle, you may prefer to visit Crumpton in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $125 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Crumpton rentals

At Expedia, we put the best Crumpton vacation 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 vacation.

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.

Explore a world of travel with Expedia

Frequently asked questions

Are there vacation rentals in Crumpton?

Yes, we give you a choice of vacation rentals close to popular local attractions in Crumpton, or you can choose a secluded option if you want a relaxing place to stay.

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

Grays Inn Creek Waterfront Pvt. Dock Kayaks & View: This vacation home near Crumpton is located on a lake and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 7 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so 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 Betterton Beach. In the larger area, you’ll find Church Hill Theatre and Rolphs Wharf Marina.

What’s a vacation rental in Crumpton like?

Vacation rentals are privately owned properties you can stay in for a few weeks or just a few days in Crumpton. Vacation rentals offer extras like laundry facilities and kitchens to help you enjoy your stay. If you're concerned about a sanitized environment, a vacation rental can provide a sense of security away from public hotel elevators and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a standard hotel, which is another reason why a vacation rental is a great option for small groups.