Holiday Rentals in Chestertown
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Check Chestertown holiday rental availability
Holiday Rentals in Chestertown
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
A waterfront gem with dock, kayaks great water views. Sleeps up to 12.
'At Fells Point' CitySide - 'Tons better than a hotel!'
'At Fells Point' CitySide - 'Tons better than a hotel!'
Waterfront w/private pier located near Rock Hall, REMODEDLED and ENLARGED for 16
Waterfront w/private pier located near Rock Hall, REMODEDLED and ENLARGED for 16
Waterfront house with amazing views. Top of the Chesapeake
Waterfront house with amazing views. Top of the Chesapeake
Amazing Waterfront Views at Sailor's Sunrise Cottage on the Upper Chesapeake Bay
Amazing Waterfront Views at Sailor's Sunrise Cottage on the Upper Chesapeake Bay
Other types of properties in Chestertown you may be interested in
Comfort Inn & Suites Chestertown
Comfort Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
Red Roof Inn & Suites Chestertown
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
350 Acre Waterfront Farm; High Speed Internet, Pool, Pickleball & Private Dock
Find out more about Chestertown
Find out more about Chestertown
Everything you need to know about Chestertown holiday rentals
Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chestertown holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 Chestertown holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.
Chestertown holiday rentals: An excellent choice for every season
Whenever you want to travel, a warm welcome awaits you in Chestertown. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .
Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chestertown holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in. The selection of Chestertown holiday rentals we have selected for you start as low as €197 per night. Entering your travel dates in the search wizard you might find even better deals!
How to find incredible deals on Chestertown rentals
At Expedia, we put the best Chestertown holiday 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 Chestertown 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 Chestertown holiday.
If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chestertown. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.