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Crumpton Vacation Rentals

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Our top choices for Crumpton vacation rentals

First Floor Studio Apartment in Historic Chestertown

First Floor Studio Apartment in Historic Chestertown
Chestertown
9.6 out of 10, Exceptional, (118 reviews)
"Hosts were extremely friendly and helpful!Parking was within feet of entrance. Studio and bathroom were spotless. Nice touches like coffee and accoutrements in the shower. Beautiful surroundings, everything was in bloom and spring beauty was everywhere!Washer and dryer in studio with soap and softener. Charming location!"
United States
Rob C.
The price is CA $140
CA $225 total
includes taxes & fees
Jul 13 - Jul 14
First Floor Studio Apartment in Historic Chestertown

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, (23 reviews)
"The stay was wonderful Just the weekend getaway we needed. Plus a wonderful host being so attentive when needed 10/10 will stay again!"
United States
Riley B.
The price is CA $96
CA $177 total
includes taxes & fees
Jul 13 - Jul 14
Guest Suite for up to 2 in a Victorian on the Chester River

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, (24 reviews)
"Close to Main Street. Very nice and spacious accommodations."
United States
Michael D.
The price is CA $176
CA $419 total
includes taxes & fees
Jul 17 - Jul 18
Walk to everything Rock Hall from this 1st floor apartment. Sleeps 4!

BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (58 reviews)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
The price is CA $255
CA $390 total
includes taxes & fees
Jul 13 - Jul 14
BAYSIDE BUNGALOW

Turtle Cove Room

Turtle Cove Room
Kent County
The price is CA $199
CA $247 total
includes taxes & fees
Jul 27 - Jul 28
Turtle Cove Room

Waterfront Retreat with Private Dock and Beach

Waterfront Retreat with Private Dock and Beach
Worton
10.0 out of 10, Exceptional, (25 reviews)
"Quiet and relaxing spot right on the water"
United States
Jennifer W.
The price is CA $318
CA $536 total
includes taxes & fees
Jul 13 - Jul 14
Waterfront Retreat with Private Dock and Beach

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 CA $214
CA $265 total
includes taxes & fees
Jul 13 - Jul 14
Beachcomber Suite

Bayside Cottage steps from Rock Hall Harbor

Bayside Cottage steps from Rock Hall Harbor
Rock Hall
10.0 out of 10, Exceptional, (4 reviews)
"Great spot, close to everything in town - had a nice visit!"
United States
Adam S.
The price is CA $347
CA $635 total
includes taxes & fees
Jul 27 - Jul 28
Bayside Cottage steps from Rock Hall Harbor

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)
"The house was lovely, very comfortable and hosts were very responsive! We will be back for another stay. "
United States
Diana S.
The price is CA $885
CA $1,225 total
includes taxes & fees
Jul 16 - Jul 17
Wren Retweet- Country Estate in Center of C’Town
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

You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation 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 or room. 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 vacation just got upgraded.

As much as you love your short-term rental, it’s always good to get out and explore to soak up . 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 . 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 vacation rental 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 vacation 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 short-term rentals, that won’t be hard to do.

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?

Serene Waterfront Cottage with dock and gorgeous views.: This vacation home rental near Crumpton is located on the waterfront and offers a garden, air-conditioning, and laundry facilities to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a microwave.

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 Rolphs Wharf Marina and Chestertown Historic District.

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.