Chestertown Vacation Rentals from CA $149: Short-Term Rentals for 2024

Check Chestertown vacation rental availability

Vacation Rentals in Chestertown

Chestertown Vacation Rental Travel Info

Number of vacation rentals	27
Popular accommodation	Chestertown private vacation homes
Known landmarks	Loon Lake Beach, Natural Stone Bridge and Caves and Friends Lake
International airport	Albany, NY (ALB-Albany Intl.)

Other types of properties in Chestertown you may be interested in

"Outstanding customer service from the front desk, Zell at the cafe, all of the restaurants staff and management. Thank you all for acknowledging our wedding anniversary!"

CA $348 total

includes taxes & fees

Jun 13 - Jun 14

" Very well kept place. "

CA $185 total

includes taxes & fees

Jun 5 - Jun 6

"Hotel very nice located. Very calm, in the nature, but near the shopping centers and the restaurent. A mention for the spa"

CA $150 total

includes taxes & fees

Jun 12 - Jun 13

Everything you need to know about Chestertown vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Chestertown vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, cottages, 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chestertown vacation 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chestertown vacation rentals we have selected for you start as low as CA $149 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 vacation 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 vacation.

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.

Frequently asked questions

Can I find vacation rentals in Chestertown?

Yes, we give you a choice of vacation rentals near well known points of interest in Chestertown, or you can choose a more remote option if you want a relaxing place to stay. Nature enthusiasts will enjoy the lakeside in Chestertown. Make sure you have time to check out the coffeehouses and forests during your trip.

What are some of the best vacation home rentals in Chestertown?

Scenic lakefront retreat with water access, private dock, grill, W/D & fireplace: You might like this vacation home rental near Chestertown. It is located on a lake and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of books.

How many vacation rentals will I find in Chestertown?

With 60 Expedia vacation rentals, you're sure to find just the right place for your Chestertown stay.

What’s there to see and do in Chestertown?

Loon Lake Beach and Friends Lake are a couple of lovely local spots to get outside and enjoy nature. Loon Lake and Hudson River are other places to visit while you're in town.

What’s a vacation rental in Chestertown like?

Vacation rentals are private properties you can book for a couple of days or more in Chestertown. Vacation rentals provide amenities like kitchens and laundry facilities so you'll have everything you want. If you're concerned about a clean environment, a vacation rental can provide a sense of security away from shared hotel elevators and busy lobbies while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular option for a small group gathering.