Crumpton Holiday Rentals

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Holiday Rentals in Crumpton

Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
9.8 out of 10, Exceptional, (36)
"Waterview cottage is comfortable and very clean. The accommodations look new and we had good sleep. The kitchen has most of the necessary equipment for meal preparation. A baking sheet pan is needed. WiFi and Roku TV was excellent. The primary bedroom bed was so tall/high my wife could not get in or out of it. That necessitated sleeping in the 2 twins. Plus, one of the twins was missing the top mini mattress. The view is mostly of the neighborhood street, nearby homes and their roofs and a small...
Waterview Cottage with Amazing Sunsets overlooking The Chesapeake Bay
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
10.0 out of 10, Exceptional, (52)
"My family of 4 stayed here. So many things to do outside-truly a good time. So many games and accessories to have an easy good time. Would definitely stay at this place again."
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
BAYSIDE BUNGALOW
10.0 out of 10, Exceptional, (16)
"We have been coming to Rock Hall for years and have stayed at the cottage the last two times and we have really enjoyed it. We will be back again and we will stay at this cottage again. My husband loves the sauna. Bill and Hannah"
The price is NZ$442
per night
5 Jun - 6 Jun
BAYSIDE BUNGALOW
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Eastern Shore beach cottage get-away
10.0 out of 10, Exceptional, (122)
"The cozy cottage is perfectly maintained and well equipped. The bay view is as advertised and lovely. The location in Rock Hall is ideal, quiet and convenient to everything. The property manager is responsive and informative. We had a great, relaxing getaway weekend and look forward to returning."
Eastern Shore beach cottage get-away
Entire Townhouse in Rock Hall
10.0 out of 10, Exceptional, (15)
"We have stayed in this neighborhood before on a previous visit, we enjoyed how quiet and friendly the neighborhood is. We will definitely visit again. The house is very, very clean, cozy, and well stocked with all the supplies you could possibly need. We enjoyed sitting out in the evenings and watching the stars!!! Thanks for making our visit complete!!!"
Entire Townhouse in Rock Hall
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
9.8 out of 10, Exceptional, (14)
"We really enjoyed our (much too short) stay at this waterfront gem!! The property was very clean, had all the amenities that we needed for our time away.... the only complaint is that we didn't have enough time to enjoy it all!! : ) thank you so much, we will be back!"
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
Waterfront Home with Private Dock, Eastern shore, Betterton Chestertown MD.
9.8 out of 10, Exceptional, (80)
"House was fine. Odd they did not provide sheets. Was difficult for folks who came from far away. But the house was lovely and we enjoyed our time there!!"
Waterfront Home with Private Dock, Eastern shore, Betterton Chestertown MD.
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
10.0 out of 10, Exceptional, (19)
"Cozy & elegant ☀️ a clean bright space."
WORLD’S BEST SUNSETS ON UPPER CHESAPEAKE BAY -CRYSTAL BEACH MANOR, EARLEVILLE,MD
Amazing Modern house with a full kitchen and parking
Amazing Modern house with a full kitchen and parking
Cozy Cape Cod nestled in the heart of Rock Hall, sleeps 10 with pond view!
10.0 out of 10, Exceptional, (2)
"Beautiful property, both inside and out, which was comfortable for two families with numerous children. Hosts were kind enough to make amenities beyond the usual available, including yard games, fishing rods, fire pit, and bicycles. We were VERY comfortable throughout our stay and were appreciative of everything this charming house had to offer. Three out of the four bedrooms had enough space for a crib, and the last still had a queen size bed that fit perfectly in the space with room to move...
Cozy Cape Cod nestled in the heart of Rock Hall, sleeps 10 with pond view!
First Floor Studio Apartment in Historic Chestertown
9.8 out of 10, Exceptional, (59)
"This was the perfect place to rest our heads along our trip down the east coast. Very comfortable, clean and quiet. We made time to visit the beautiful town and I’m glad we did!"
The price is NZ$269
per night
1 Jul - 2 Jul
First Floor Studio Apartment in Historic Chestertown
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
10.0 out of 10, Exceptional, (3)
"Lark’s Nest was a cute little place! Very clean! The view from the patio was stunning, and if you’re a bird lover you will be in your glory! Bring your binoculars and sit on the deck and wait! House was well equipped with most everything you would need! Host was very quick to write back when asked a question! First time in this area and hopefully be back again in the future!"
Lark's Nest on the Chester River. Spacious, waterfront home with private dock.
Centreville Waterfront Farm | 170 Acres | Pool | Private Dock | Private Beach |
10.0 out of 10, Exceptional, (3)
"Wonderful rental home for our family with great pool and river view. Swimming every day in the pool was so much fun for everyone, kayaks, and paddle boards were great since we did not have to bring anything. Children fished every night on the dock. We played lots of games inside and out everyday and enjoyed the Nature all around to see, birds, deer, fish, frogs and small animals. Our family felt like they had their own getaway for a wonderful vacation. Thank you for everything."
Centreville Waterfront Farm | 170 Acres | Pool | Private Dock | Private Beach |
Guest Suite for up to 2 in a Victorian on the Chester River
The price is NZ$204
per night
1 Jul - 2 Jul
Guest Suite for up to 2 in a Victorian on the Chester River
200 steps to the beach!
10.0 out of 10, Exceptional, (75)
"Great stay over Memorial Day weekend. Loved the location of the house...so close to the water and not crowded at all. We will definitely be back!"
200 steps to the beach!
Ruby's Sea Glass Cottage near Betterton Beach
10.0 out of 10, Exceptional, (10)
"We had a lovely weekend stay at Ruby’s sea glass cottage. It is newly renovated, completely outfitted with every amenity you could want or need, and walking distance to the beach and park. We enjoyed playing pickleball on the park’s courts and riding bicycles, grilling out and eating on the back porch, and sleeping in the comfortable beds! We were even entertained on the rainy morning as we played games and worked puzzles that the owner has on hand. A fantastic home that we heartily recommend!"
Ruby's Sea Glass Cottage near Betterton Beach
Lovely Home in Chestertown Which Sleeps 7 - Free EV Charging for guest
10.0 out of 10, Exceptional, (2)
"An absolutely beautiful home!!! The host thought of everything to make our stay fantastic…"
Lovely Home in Chestertown Which Sleeps 7 - Free EV Charging for guest
Historic Downtown Garden Oasis with Private Patio
10.0 out of 10, Exceptional, (14)
"Stephen and Marianna were great hosts. The property was very clean and functional with beautiful artwork throughout the property. Great outdoor patio for relaxing plus excellent location for access to downtown Chestertown. We will be staying here again on our next visit."
Historic Downtown Garden Oasis with Private Patio
Country Estate in Historic District
10.0 out of 10, Exceptional, (63)
"Place is FABULOUS!!! Fantastic location easy to walk around town. THANKS FOR EVERYTHING"
Country Estate in Historic District
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
10.0 out of 10, Exceptional, (28)
"I organized a large (15 person) bachelorette weekend at this property in early April. It is an absolutely gorgeous house and the host had a number of thoughtful touches - like extra firewood for the firepit, coffee supplies, and a bottle of bubbly for our bride! The beds were comfortable (even the twins!), which was lucky because one bedroom on the breakdown was not really usable, so a handful of guests relocated to one of the 'kid rooms.' We found Ashleigh very responsive both before and...
Stunning 9-Bedroom Villa on the Chesapeake Bay: Pool, Hot Tub, Boat Dock & Sauna
Don't see what you're looking for?
See all available properties in Crumpton
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.

Other types of properties in Crumpton you may be interested in

Quality Inn
2.5 star property
7.6 out of 10, Good, (882)
"Fine"
The price is NZ$182
per night
3 Jun - 4 Jun
Quality Inn
Comfort Inn & Suites Chestertown
2.5 star property
8.6 out of 10, Excellent, (677)
"Breakfast area and food was below expectations"
The price is NZ$236
per night
2 Jun - 3 Jun
Comfort Inn & Suites Chestertown
Holiday Inn Express And Suites Middletown, an IHG Hotel
2.5 star property
9.2 out of 10, Wonderful, (441)
"The staff was very nice and accommodating. I needed a shower chair and they were able to provide it without a hassle. The rooms were clean and up to date. "
The price is NZ$227
per night
1 Jul - 2 Jul
Holiday Inn Express And Suites Middletown, an IHG Hotel
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.

You always said you would go on a dream holiday someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannonball into the deep end. Go ahead, unplug and unwind in style. When you book one of our Crumpton holiday rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your holiday just got upgraded.

As much as you love your vacation rental, it’s always good to get out and explore to soak up Crumpton. Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in Crumpton. Seeing all the best attractions is bound to make you fall in love with Crumpton. Who knows, you may even be tempted to extend your stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true. 

It’s your escape so why share it? You deserve your own slice of paradise. Booking your holiday rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in Crumpton short-term rentals, that won’t be hard to do.

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?

350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock : This holiday home rental outside of Crumpton is located on a lake, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. It offers a balcony, 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 Rolphs Wharf Marina and Washington College.

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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