Chestertown Vacation Homes

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Featured Vacation Homes in Chestertown

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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.

Hotel Options in Chestertown

    Red Roof Inn & Suites Chestertown

    Red Roof Inn & Suites Chestertown

    160 Scheeler Rd, Chestertown, MD
    The price is $76 per night from May 7 to May 8
    $76
    includes taxes & fees
    $68 per night
    May 7 - May 8
    7.2/10 Good! (345 reviews)
    Comfort Inn & Suites Chestertown

    Comfort Inn & Suites Chestertown

    150 Scheeler Road, Chestertown, MD
    The price is $122 per night from May 7 to May 8
    $122
    includes taxes & fees
    $110 per night
    May 7 - May 8
    8.4/10 Very Good! (758 reviews)
    The Lodge at Great Oak Landing

    The Lodge at Great Oak Landing

    22170 Great Oak Landing Rd, Chestertown, MD
    The price is $163 per night from May 4 to May 5
    $163
    includes taxes & fees
    $147 per night
    May 4 - May 5
    7.6/10 Good! (48 reviews)

Chestertown Vacation Homes

Book vacation homes in Chestertown
Next time you take a group getaway top Chestertown, don’t confine your friends and family to one or two hotel rooms. Instead, snag a deal on a full-sized house and get the best of both worlds. Vacation home rentals are perfect for families and large groups that want to live like locals on vacation. Whether you are searching for a villa that pulls out all the stops or a four-bedroom house to host the best summer vacation ever, Orbitz has a variety of Chestertown vacation homes for rent that are ideal for you. Your perfect pad is only a few clicks away.

Homes for every Chestertown vacation
If you’re planning a vacation with a lot of people, you’ll want room to stretch out, and a rental home has plenty of space. Many vacation homes also come with everything you’ll need for a proper getaway, like kitchens with every gadget you can think of, along with updated furnishings, fancy spa tubs and balconies. You may even wind up in a rental home that has a sprawling backyard for barbecues, games and general relaxation. These rentals offer the added bonus of putting you right in the thick of things in Chestertown; instead of going to a small hotel room at the end of a busy day, you’re going home.

Vacations are all about creating lasting memories, and a Chestertown rental home makes it easy to create good ones. Whether you’re getting the college crowd back together or bringing along your folks and your kids, a trip to Chestertown is sure to be a winner.

Chestertown Vacation Homes essential information

Accommodation
524 Vacation Homes
Lowest Price
$76
Highest Price
$261
Popular accommodation
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street! , 240' Private Beachfront @Kent Island Love Point - Great for Large Groups, Captivating Chesapeake experience, ❤️Charming Coastal/Country Home w/3 Acres & Sauna!❤️, Historic Annapolis Home 1.5 blocks from center of town., Waterfront w/upper sundeck and private pier located near Rock Hall, sleeps 18., Entire House by the Fells Point, JHU., Steps to USNA Gate 3 at historic Gatehouse, on-site parking, PERFECT LOCATION in the heart of history