Chestertown Holiday Rentals from €114: Search Short-Term Rentals

Q: What are some of the best holiday rentals that Chestertown has to offer?

Elizabeth. 15 minutes to Lake George.Seasonal Heated Pool. : This highly rated holiday home rental in Chestertown is located on the waterfront, and has an outdoor pool, a balcony and a BBQ to put you at ease in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games. Our travellers also rate Eagles Nest at Loon Lake near Gore Mountain as a favourite home for rent in Chestertown.

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Chestertown holiday rentals

A view through a window of a deck area with outdoor furniture and a barbecue grill.

1. The Lily Pad at Loon Lake near Gore Mountain

Chestertown

Sara Beth E.

includes taxes & fees

27 Sept - 28 Sept

A log cabin interior with a stone fireplace, wooden ceiling beams, and a large leather sofa.

2. Authentic Log Cabin with Lake Views and Sauna

Chestertown

Joe F.

includes taxes & fees

28 Sept - 29 Sept

A wooden deck with a grill, two red chairs, and a welcome sign.

3. Adirondack Mountains Cottage Near Gore Mountain!

Warrensburg

Jennie M.

includes taxes & fees

25 Sept - 26 Sept

A compact kitchen with white cabinets, a stainless steel refrigerator, a microwave, a dishwasher, and a coffee maker.

4. Gore MTN & Saratoga ADK Crash Pad! The Cocoon

Warrensburg

Matthew L.

includes taxes & fees

29 Sept - 30 Sept

A two-story building with a balcony and a flag.

5. Penthouse w/ Best Mtn Views Walk to Gore, Main St | Fast WiFi | Sleeps 6

North Creek

Michael

includes taxes & fees

28 Sept - 29 Sept

A covered porch with a table and chairs, overlooking a residential area with houses and a street.

6. Gore Mountain Lift View: North Creek Main St Apt 2

North Creek

Lynda N.

includes taxes & fees

28 Sept - 29 Sept

A lakeside cabin with a wooden deck and a view of the lake.

7. Trout House Village Resort

Hague

Matthew

includes taxes & fees

20 Oct - 21 Oct

A white building with a red umbrella, a stone chimney, and a black fence in front.

8. Adirondack Bungalow Getaway

Warrensburg

Virginia (Ginger) S.

includes taxes & fees

28 Sept - 29 Sept

View all properties

Find holiday rentals that suit your style

Cabins

Cottages

Save an average of 15% on thousands of hotels when you're signed in

Sign in

Sign up, it's free

Top Chestertown Hotel Reviews

Nordick's Inn

8/10 Good

"Great location, a short walk to the center of town (under 10 minutes), friendly staff. Parking available."

Tiki Resort

8/10 Good

"The room was updated nicely including a nice bathroom and shower. Beds were nice and all furniture in the room were new. Just 2 areas for improvements. The WIFI does not work in the rooms that are detached from the main building. Every time you try to connect the same message comes up and says cannot connect to WIFI at the time. Yet when you go into the main building you hook up right away. All that is needed is a repeater if proper strength attached to the building of rooms to correct this problem. This was the same problem the last time it stayed there. The other problem is it appears that the floors are not mopped after each stay. The evidence was I dropped a bit of water on the floor. I took a tissue to dry it up and the tissue turned black. We had just checked into the room. There is no reason why after each stay the main traffic areas which is very small is not properly mopped to keep the floor clean. No other issues."

Find out more about Chestertown

Everything you need to know about Chestertown holiday rentals

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

Chestertown holiday 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 holiday 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 holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chestertown holiday rentals we have selected for you start as low as €114 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 holiday 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 holiday.

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 holiday rentals in Chestertown?

Yes, there are holiday rentals close to the most popular sights in Chestertown, or you can select a more secluded option if you're looking for a relaxing stay. Nature enthusiasts will enjoy the lakeside in Chestertown. Make sure you have time to check out the coffee shops and forests during your trip.

What are some of the best holiday rentals that Chestertown has to offer?

Elizabeth. 15 minutes to Lake George. Seasonal Heated Pool.: This highly rated holiday home rental in Chestertown is located on the waterfront, and has an outdoor pool, a balcony and a BBQ to put you at ease in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games. Our travellers also rate Eagles Nest at Loon Lake near Gore Mountain as a favourite home for rent in Chestertown.

How many holiday rentals will I find in Chestertown?

With 62 Expedia holiday rentals, you're guaranteed to find just the right place for your Chestertown stay.

What’s there to see and do in Chestertown?

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

What’s a holiday rental in Chestertown like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Chestertown. Holiday rentals provide amenities like kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about a sanitised environment, a holiday rental can offer a sense of security away from shared hotel lifts and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental an attractive choice for family trips or small group gatherings.

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Chestertown holiday rentals

1. The Lily Pad at Loon Lake near Gore Mountain

2. Authentic Log Cabin with Lake Views and Sauna

3. Adirondack Mountains Cottage Near Gore Mountain!

4. Gore MTN & Saratoga ADK Crash Pad! The Cocoon

5. Penthouse w/ Best Mtn Views Walk to Gore, Main St | Fast WiFi | Sleeps 6