Crumpton Vacation Rentals

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Vacation Rentals in Crumpton

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.
$257 nightly
The price is $284
Nov 15 - Nov 16
Total with taxes and fees
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

First Floor Studio Apartment in Historic Chestertown

Chestertown
9.6 out of 10, Exceptional, (106)
"Wonderful stay in a beautiful location convenient to everything. Host was outstanding."
United States
Randy B.
$144 nightly
The price is $159
Nov 17 - Nov 18
Total with taxes and fees
First Floor Studio Apartment in Historic Chestertown

Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!

Chestertown
10.0 out of 10, Exceptional, (10)
"Check-in was very easy. House was clean and well supplied with everything we needed. Peaceful and quiet. Mowed and cleared trails to enjoy. "
United States
Carol B.
Outrange at Blue Heron Farm. Pet friendly cabin at waterfront farm!

Stunning Historic Downtown Home!! Within 2 Blocks of Fountain Park!!

Chestertown
10.0 out of 10, Exceptional, (2)
"Overall a beautiful and well maintained place to stay! The location was perfect…within walking distance to everything! A very charming home! We were so happy we chose this property!"
United States
Dawn B.
Stunning Historic Downtown Home!! Within 2 Blocks of Fountain Park!!

BAYSIDE BUNGALOW

Rock Hall
10.0 out of 10, Exceptional, (52)
"This stay was a wonderful, relaxing experience. The hosts were so friendly and welcoming and the cottage was charming. We lacked for nothing and especially enjoyed the bikes and the chance to bike around this lovely area. Highly recommend!"
United States
Jackie R.
BAYSIDE BUNGALOW

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

Earleville
9.8 out of 10, Exceptional, (59)
"Wonderful house in a welcoming, friendly community. "
United States
Benjamin A.
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay

Stunning waterfront villa with indoor pool and kids swing set and play area.

Earleville
9.8 out of 10, Exceptional, (19)
"Wonderful location, lots to do, close to Chesapeake City, excellent host"
United States
Ann P.
Stunning waterfront villa with indoor pool and kids swing set and play area.

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

2.5 star property
Rock Hall
10.0 out of 10, Exceptional, (1)
"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.
$257 nightly
The price is $272
Nov 15 - Nov 16
Total with taxes and fees
Chesapeake Bay Harbor View in a central location to events/restaurants

200 steps to the beach!

Rock Hall
10.0 out of 10, Exceptional, (93)
"This place was so nice.It exceeded all of our expectations Great nautical decorating Very lot of spaceWe stayed at a lot of different places for Pirates weekend in the last 15 years and this is our favorite. We would like to stay again next year. One of our favorite parts of pirate weekend is the beach party and we were right there "
United States
WAYNE W.
200 steps to the beach!

Stay in the landmark Lighthouse!

Rock Hall
10.0 out of 10, Exceptional, (107)
"Beautiful home. Wish I could of stayed longer "
United States
Pat R.
Stay in the landmark Lighthouse!

Circa 1900 Home in the Heart of Historic Downtown Chestertown

Chestertown
10.0 out of 10, Exceptional, (76)
"Lovely, well kept and tastefully furnished house in a great location."
United States
Darren H.
Circa 1900 Home in the Heart of Historic Downtown Chestertown

Spacious Victorian close to everything in RH - Wheelchair friendly. Sleeps 11

Rock Hall
10.0 out of 10, Exceptional, (20)
"It was very convenient using this house and location as our base. Glad we picked this house for our weekend stay."
United States
Doug W.
Spacious Victorian close to everything in RH - Wheelchair friendly. Sleeps 11

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

Rock Hall
10.0 out of 10, Exceptional, (29)
"Very quaint, clean. The check in was very easy."
United States
Patty M.
Peaceful Retreat on the Eastern Shore. Nature lover’s paradise!

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

Rock Hall
10.0 out of 10, Exceptional, (8)
"Great house everything you need plenty of room convenient to rock hall and tolchester, will stay again "
United States
Ken S.
Amazing Waterfront house with expansive views of the Chesapeake Bay and Sunsets

Waterfront Retreat with Private Dock and Beach

Worton
10.0 out of 10, Exceptional, (25)
"Loved sitting on the dock, peaceful, quiet; house has everything you need"
United States
jackie r.
$282 nightly
The price is $311
Nov 16 - Nov 17
Total with taxes and fees
Waterfront Retreat with Private Dock and Beach

Historic 2 Bed/2 Bath Downtown Loft w/Park View & Spa Access

Chestertown
10.0 out of 10, Exceptional, (3)
"Very nice and clean. Would stay again if in the area. Very good location."
United States
Us
Historic 2 Bed/2 Bath Downtown Loft w/Park View & Spa Access

Serene Waterfront Cottage with dock and gorgeous views.

Rock Hall
9.6 out of 10, Exceptional, (38)
"Nice place with everything I could want. Would stay there again!"
United States
Eric H.
Serene Waterfront Cottage with dock and gorgeous views.

Waterfront Lodge packed with Amenities

Earleville
10.0 out of 10, Exceptional, (3)
"Beautiful home. Gorgeous views of Bohemian River. Well maintained House and fully supplied. Our families and friends just loved it. They were already speaking about wanting to return again. "
United States
Virginia G.
Waterfront Lodge packed with Amenities

Luxurious and spacious townhome with all necessary amenities awaits your stay.

Middletown
9.4 out of 10, Exceptional, (9)
"Just like the pictures. Very clean and comfortable.Highly recommend!"
United States
Patricia Z.
Luxurious and spacious townhome with all necessary amenities awaits your stay.

Countryside Cottage in Sassafras

2.0 star property
Galena
10.0 out of 10, Exceptional, (1)
"Very nice home. Peaceful setting."
United States
James L.
Countryside Cottage in Sassafras
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

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 $159 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.

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?

Chesapeake Bay Harbor View in a central location to events/restaurants: This vacation home rental near Crumpton is located in a rural location and has an outdoor pool, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Make the most of the garden in this rental home to help you unwind.

What’s there to see and do in Crumpton?

Explore the area and family-friendly sights such as Hazel Miner Monument, or get out into nature at a spot like Betterton Beach. In the larger area, you’ll find Tilmon's Island Winery and Crow Farm and Vineyard.

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.