Book a Cabin in Chestertown, MD

Get adventurous in the outdoors by day and experience complete comfort at night at one of our cabins near Chestertown. With rates ranging between $401 and $401 a night, you’re bound to find something that’s perfect for you. Prices reflect current offers and availability is subject to change. Additional terms may apply.

Find a cabin rental in or around Chestertown that matches your style for as little as $401 per night. This was the lowest price available in the last seven days. Prices reflect current offers and availability is subject to change. Additional terms may apply.

There are 33 cabin retreats to rent around Chestertown, so find your perfect lakeside or mountain cabin with Travelocity. Great options here include Cozy Cabin Happiness and Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay.

Book a stay in one of our cheap cabin rentals and you’ll have adventure aplenty within your reach. Tailor-made for family groups of almost any size, Chestertown cabins are a popular base for discovering everything the area has to offer.

• At the top of the list of family attractions to discover is Lewes Beach. From Chestertown, it’s around 95 mi away to the southeast and a superb spot to spend time together.
• You’ll want to have enough space on your phone to take some fun family photos at Sunset Beach. This spot is about 100 mi to the east of Chestertown.
• If you’re looking for someplace that’ll delight the entire gang, Breezy Point Beach will tick your boxes. This top family-friendly spot is about 75 mi to the southwest of Chestertown.

Explore your surroundings together or kick back with a favorite board game. However you prefer to spend time with your gang, these family-friendly cabins near Chestertown ensure a vacation to remember:

• Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay - This charming stay has handy amenities such as a meal delivery service and a travel crib.
• Country Coziness - Lancaster County Private Cabin - Settle in for a few nights here and enjoy access to a deck, a toaster and more.

Go for a dip, drop a line in or just settle back and let the melodic sounds of the river lull you into a state of total relaxation. If you’re after someplace that combines comfort and outdoor adventure, take a look at these river cabins near Chestertown:

• Cabin - - Picturesque Wooded Property With Unique Tiny House — Get away from it all at this popular riverside retreat. It offers on-site watersports, outdoor furniture and more.
• Cabin - Vintage Waterfront A Frame - Hideaway On The Bay — With on-site watersports, a firepit and plenty of other amenities, this place has everything you need for a comfortable stay.

Pack your one-piece and inflatable unicorn. A Chestertown cabin with a pool is the ideal escape, blending comfort, nature and splashing great fun! Jump into one of these superb options:

• Arrange a stay at Country Coziness - Lancaster County Private Cabin. There are lots of handy amenities here including a swimming pool and a patio.
• Alternatively, spend your escape at Amazing Getaway: Enjoy Our Cozy Log Cabins On The Chesapeake Bay. A swimming pool and a patio are among the conveniences this place offers.

When you’re ready to reconnect with nature, stay at one of our Chestertown cabins. Whether you’re looking for a romantic getaway cabin for you and your sweetheart or a retreat that’ll fit the whole family, we’ve got options to suit all needs and budgets.

• Consider Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay and experience the wilderness without having to rough it. Amenities here include a firepit and a fireplace.
• Another great option for your peaceful escape is Pet - Friendly Lakeview Cabin W. A deck and a dock help make this place a favorite with travelers.

For cheap cabin rentals or Chestertown family cabins, enter your travel details, then use our page filters to refine your search by price, guest rating, location and more. If you think your plans may change, opt for properties with free cancellation for more peace of mind. Also, Travelocity’s Price Guarantee means if you come across the same cabin for a cheaper price within 24 hours of booking, we’ll refund you the difference. Get the ball rolling on your fun-filled vacation and book your Chestertown cabin today!