Photo by Julie Miller

Holiday Rentals in Chestertown

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

Next weekend
In two weeks

Holiday Rentals in Chestertown

Eagles Nest at Loon Lake near Gore Mountain

Chestertown
10.0 out of 10, Exceptional, (113)
"Great place to stay for gore mountain, will come again"
United States
Joseph V.
Eagles Nest at Loon Lake near Gore Mountain

Lincoln Log Colony

2.0 star property
Lake George
8.8 out of 10, Excellent, (10)
"This is a great property. Initially we rented a large “suite” but immediately upgraded to one of their adorable cabins just across from the playground and pool. The property has super nice and accommodating staff, plenty of parking and really nice families staying there; some are regulars for 20, 40 years! This is truly a family stay place and we were so happy to have found it. Now we’re planning to return year after year! Two beautiful Adirondack chairs on a quiet little stoop outside of each...
United States
Jill
Lincoln Log Colony

Terrace on the Lake – Private Lakefront with Breathtaking Views

Warrensburg
10.0 out of 10, Exceptional, (328)
"Everything was excellent and the house is amazing!"
United States
Josh R.
Terrace on the Lake – Private Lakefront with Breathtaking Views

Waterfront Home on Lake George w/ Boat Dock!

3.0 star property
Queensbury
Waterfront Home on Lake George w/ Boat Dock!

ADK Riverside Retreat-Heated Pool-Hot Tub- close to Lake George and Gore

Warrensburg
9.8 out of 10, Exceptional, (191)
"Amazing property, clean and roomy"
United States
Chris C.
ADK Riverside Retreat-Heated Pool-Hot Tub- close to Lake George and Gore

Spacious log cabin in Warrensburg w/ Hot Tub: 15 Mi to Lake George

Warrensburg
9.6 out of 10, Exceptional, (5)
"The three days my friends and I stayed at the cabin was the most fun we’ve had in a while. The house is full of amenities that guarantee you have an amazing stay. From the hot tub to the pool table to even just hanging out by the fire. We had an immaculate stay. The surrounding area has multiple stores and swimming holes including lake George which is a 20 minute drive away. The host couldn’t have been better, Responding within minutes and being very understanding of any issues. Booking this...
United States
Jared M.
Spacious log cabin in Warrensburg w/ Hot Tub: 15 Mi to Lake George

Trout House Village Resort

3.0 star property
Hague
9.8 out of 10, Exceptional, (17)
"Beautiful views and wonderful staff. Provides an atmosphere for activities and relaxation while being able to access anywhere on the lake."
United States
John
The price is €165
includes taxes & fees
10 Nov - 11 Nov
Trout House Village Resort

Private Adirondack Getaway. Stunning Fall Foliage. Close to Lake George and VT.

Clemons
10.0 out of 10, Exceptional, (100)
"My family and I loved the stay. Great place to enjoy the nature. The house had everything we needed such as great kitchen, fireplace, and jacuzzi. "
United States
Herman K.
Private Adirondack Getaway. Stunning Fall Foliage. Close to Lake George and VT.

luxury log home mins from Lake George, w/ heated salt water pool!

Warrensburg
10.0 out of 10, Exceptional, (168)
"We had the best time with an extended family group from ages 3-65 including my handicapped brother. It’s a great layout for a big group and those with limited mobility with just a few steps up to the house and everything you need on one level. The outside space is amazing and my kids were in the pool and using the playset all day every day! Truly the house had everything you need and the hosts are super nice and responsive. "
United States
Betsy H.
luxury log home mins from Lake George, w/ heated salt water pool!

Ultimate Adirondack Getaway ~ Private Pool and Hot Tub!

Warrensburg
9.8 out of 10, Exceptional, (335)
"We had a great week at this lovely home, something for everyone!The owners were very responsive to our needs!!I would definitely recommend this rental home!"
United States
Pamela L.
Ultimate Adirondack Getaway ~ Private Pool and Hot Tub!

PET-FRIENDLY - Twilight Cabin a Unique Waterfront Log Cabin

North Creek
9.8 out of 10, Exceptional, (102)
"What a beautiful place to stay. The cabin itself is cute and comfortable. The location is awesome."
United States
Dena M.
PET-FRIENDLY - Twilight Cabin a Unique Waterfront Log Cabin

Warm Secluded Adirondack Chalet with Game Room and Bar/Lounge

Warrensburg
9.8 out of 10, Exceptional, (49)
"Lots of space, beautiful property. Kids had a blast outside and loved the little loft bedroom outside of our master."
United States
Cassandra W.
Warm Secluded Adirondack Chalet with Game Room and Bar/Lounge

Cozy, pet friendly, newly renovated chalet home with shared beach & water views

Lake George
9.2 out of 10, Wonderful, (18)
"Had a nice view of the lake, really close to town and neighborhood is quiet"
United States
Ryan B.
Cozy, pet friendly, newly renovated chalet home with shared beach & water views

Walk to Million Dollar Beach from this awesome Cottage!

Lake George
10.0 out of 10, Exceptional, (167)
"Property was very clean and was close to downtown and the beaches . Would stay here again"
United States
Lori S.
Walk to Million Dollar Beach from this awesome Cottage!

Family Friendly - Pet Friendly

Lake George
9.8 out of 10, Exceptional, (67)
"nice clean cottage, not exactly the two bedroom set up you'd expect "
United States
Anna S.
Family Friendly - Pet Friendly

WATERFRONT and AFFORDABLE

Warrensburg
8.0 out of 10, Very good, (32)
"We absolutely loved our stay in the cabins! They were warm and cozy, making for an amazing experience. Being by the river was incredible - falling asleep to the sound of the water was pure bliss. We also had a blast swimming in the lake with the baby. The cabin itself was spotless and very welcoming. Overall, we'd give it a well-deserved 5 out of 5 stars. Can't wait to come back!"
United States
Ruth G.
WATERFRONT and AFFORDABLE

Cozy Family Friendly Lake View Home w / Easy Trip to Town & Beach

Bolton
9.6 out of 10, Exceptional, (178)
"Great location! Easy walk to town. Amazing view of the lake. "
United States
Anonymous traveller
Cozy Family Friendly Lake View Home w / Easy Trip to Town & Beach

Lake George Waterfront Paradise Dock Slip

Putnam Station
10.0 out of 10, Exceptional, (4)
"Beautiful house, amazing stay, great views! We enjoyed it!"
United States
Dawid R.
Lake George Waterfront Paradise Dock Slip

New Lakeside Cottage 5 minutes from great hiking with large deck and lake view

Silver Bay
10.0 out of 10, Exceptional, (33)
"We had a great time at this home. The hosts were very welcoming and accommodating- they gave us a heads up about a great fireworks show at silver bay. The property was well maintained with a great kitchen and comfortable beds. I’d highly recommend this for a family stay on Lake George "
United States
Chris D.
New Lakeside Cottage 5 minutes from great hiking with large deck and lake view

Direct lakefront cottage with wood burning fireplace in great room. Pet friendly

Putnam Station
8.4 out of 10, Very good, (18)
"The spectacular views from the back porch were amazing. We were in the area for a retirement party so we did not spend as much time at the house as we would have like to. "
United States
Kristin v.
Direct lakefront cottage with wood burning fireplace in great room. Pet friendly
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Save an average of 15% on thousands of hotels when you're signed in

Top Chestertown Hotel Reviews

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 €165 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?

Terrace on the Lake – Private Lakefront with Breathtaking Views: This holiday home rental outside of Chestertown is located on a lake, and has a fireplace, a balcony and a BBQ to put you at ease in your new surroundings. It has 8 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a garden, a selection of games and 1 hot tub so that you can immerse yourself in your holiday.

How many holiday rentals will I find in Chestertown?

With 58 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?

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 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.