Book Cabin Rentals in Chestertown

Flee the hustle and bustle and stay at one of our charming cabins near Chestertown. From $99 to $225 a night, they perfectly blend comfort, adventure and nature. Prices reflect current offers and availability is subject to change. Additional terms may apply.

Lock in a Chestertown cabin vacation from as low as $99 a night. This is based on prices in the last seven days. Prices reflect current offers and availability is subject to change. Additional terms may apply.

There are 383 options to suit all comfort levels and budgets around Chestertown. If you’re interested in a luxurious getaway, consider Cabin - Romantic Retreat: Mt. Views, Hot Tub and its attractive surroundings. Trying to watch your travel budget? Cabin - Kamp Koby - Lake Front Camp On Lake Hortonia is another popular choice that’s kinder to your savings account.

Choose one of our cheap cabin rentals and you’ll have boundless adventure within reach. Perfectly suited for family groups of almost any size, Chestertown cabins are an appealing base for discovering the very best of this area.

• At the top of the list of family attractions to see is Prospect Mountain. From Chestertown, it’s around 16 mi away to the south and a popular spot to spend time together.
• Yaddo Gardens, about 40 mi to the south of Chestertown, is another interesting day trip. Charge up your camera and take some pictures with the family here.
• Lastly, Whiteface Mountain is around 50 mi to the north of Chestertown. It’s the ideal spot to keep the kids on the go and make some lasting family memories at the same time.

If getting up in the morning to glorious landscapes and the sounds of wildlife is your idea of the perfect vacation, take a peek at these Chestertown mountain cabins. From cheap, comfortable stays to deluxe hideaways, we’ve got cabin rentals to suit every budget and style:

• Deer Run, Pool, Adirondack Cabin is a fantastic base for a scenic mountain getaway. Lock in a few nights and take advantage of amenities like snow sports gear and a kitchen.
• Another comfy place where you can reacquaint yourself with nature is Log Haven, Pool And Ac, Cozy Adirondack Mountains Cabin Steps From Loon Lake. A microwave oven and a firepit are among the amenities you can make use of.

Spend your days fishing, canoeing or exploring nature and your nights drifting off to the peaceful sounds of the river. Whether you’re organizing a much-needed escape with friends and family or alone, we’ve got Chestertown cabins by the river to take your pick of:

• Log Haven, Pool And Ac, Cozy Adirondack Mountains Cabin Steps From Loon Lake — Swap the busy city for a few nights in the great outdoors at this comfy riverside escape. Top amenities include a firepit and a nearby beach.
• Pet-Friendly Bolton Vacation Rental w/ Game Room! — With pet-friendly facilities, air conditioning and plenty of other great amenities, this rental has everything you need for a pleasant stay.

If you want to create a big splash on your next trip, go for a Chestertown cabin with a pool. Spend every day having fun in the water at one of the following options:

• Organize a stay at Deer Run, Pool, Adirondack Cabin and spend loads of lazy days kicking back in the water. Other top amenities include a swimming pool and a firepit.
• Or, enjoy some downtime at Log Haven, Pool And Ac, Cozy Adirondack Mountains Cabin Steps From Loon Lake. A swimming pool and a firepit are among the conveniences this place comes with.

Cool off in the water, go for a romantic walk along the shoreline and enjoy picturesque ocean views. There are plenty of awesome seaside experiences to be had when you stay at one of these Chestertown beach cabins:

• Enjoy a taste of coastal living at Cabin - Lakefront Bolton ‘alderbrook Chalet’ W. It has everything you need for a vacation by the sea, including on-site watersports and children’s activities.
• It won’t take you very long to see why Bolton ‘alderbrook Lodge’ W is also a favorite with travelers. Top amenities here include on-site watersports and clothes washing facilities.

Scroll through Travelocity’s amazing array of cabins by location, amenities and price using our handy filter option. Whether you need a Chestertown family cabin with ample room for a small army or a cozy hideaway for just you and your partner, we’ll help you find your perfect match. If you think your plans could change, select a property with free cancellation.