Book a Cabin in Chestertown, MD

Wake up to the lovely sounds of nature at one of our cabins near Chestertown, priced between $315 and $315 a night. Prices reflect current offers and availability is subject to change. Additional terms may apply.

Find a cabin in or around Chestertown that fits your style for as little as $315 per night. This was the cheapest rate offered in the last seven days. Prices reflect current offers and availability is subject to change. Additional terms may apply.

You can choose from 22 different cabins in and around Chestertown. From rustic retreats to mountain getaways, there’s a place to suit every kind of traveler here. Two top options include Cozy Cabin Happiness and Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay.

Secluded in nature yet intimate and cozy, Chestertown cabins are wonderful bases for families. Reserve one of our cheap cabin rentals and spend your trip chasing after adventure.

• Buckle up and drive to Lewes Beach. It’s around 60 mi southeast of Chestertown and a favorite among travelers young and old.
• Sunset Beach, about 60 mi to the east of Chestertown, is another unmissable excursion. Pull out your camera and capture a beautiful family photo together.
• If you’re escaping with the kids, treat them to a day out at Breezy Point Beach. It’s around 50 mi to the southwest of Chestertown and a favorite among families.

Enjoy the great outdoors, sit in the hot tub, repeat. If that’s the sort of retreat you want, these Chestertown cabin rentals with hot tubs will hit the spot:

• Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay – You’ll enjoy going for a steaming hot plunge after a big day of sightseeing. A firepit and a spa tub help make this retreat a top pick for travelers.
• Elk River Cabin - 13 Acres, Water Views – Stay at this popular place and you’ll have use of the hot tub, a spa tub, a king bed and more.

If you want to create a big splash on your next adventure, reserve a Chestertown cabin with a pool. Spend every day having a blast in the water at one of these popular options:

• Make a reservation at Amazing Getaway: Enjoy Our Cozy Log Cabins On The Chesapeake Bay. You’ll find lots of useful amenities here including a swimming pool and a tennis court.
• Or, spend your getaway at Cabin - Maryland Vacation Rental With Private Dock And Pool. A firepit and a patio are among the conveniences this getaway offers.

When you’re ready to venture into Mother Nature, stay at one of our Chestertown cabins. Whether you’re seeking a romantic getaway cabin for you and your love or a spot that’s family-friendly, we’ve got options to suit all needs and budgets.

• Spend your days in the great outdoors and your nights relaxing at Waterfront Cabin With Spectacular Sunsets Overlooking The Chesapeake Bay. This cabin retreat comes with nearby museums and a nearby waterfront.
• You’ll love coming home to August 25 - 31 Get 4 Or 5 Nights Plus 1 Free Night. Gorgeous Cabin Private Pool after a full day of adventurous activities. Put your feet up and make use of its creature comforts like nearby museums and a swimming pool.

Enter your destination, dates and number of guests, then use the nifty filter tool to tailor the results. From cheap cabin rentals that are nice and cozy to family cabins large enough for the entire family, we’ve got your next vacation covered. Travelocity’s Price Guarantee also means you’re guaranteed an unbeatable deal. For even more peace of mind, choose a Chestertown cabin with free cancellation, just in case your plans get upended.