Photo by Julie Miller

Chestertown Holiday Rentals

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Holiday Rentals in Chestertown

Lakefront cabin with beautiful loft, game room, views, private dock

9.2 out of 10, Wonderful, (36)
"Loved everything from the coffee maker to the views at this place. Fantastic!"
Lakefront cabin with beautiful loft, game room, views, private dock

Year round Log Cabin on Loon Lake. Minutes from skiing at Gore Mountain

9.8 out of 10, Exceptional, (84)
"Wonderful stay. Owner very accomodating. We had everything we needed."
Year round Log Cabin on Loon Lake. Minutes from skiing at Gore Mountain

Eagles Nest at Loon Lake near Gore Mountain

10.0 out of 10, Exceptional, (106)
"A fantastic location for those looking to get away in the Adirondacks. Conveniently close to Chestertown, as well as many outdoor activities, Eagles Nest was an awesome location to stay at with friends and family. "
Eagles Nest at Loon Lake near Gore Mountain

Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George

10.0 out of 10, Exceptional, (60)
"My family and i had a great time here! The place is Amazing and we would definitely stay again! "
Unique Adirondack Estate on Hudson River - near Gore Mountain & Lake George

Trout House Village Resort

3.0 star property
10.0 out of 10, Exceptional, (7)
"Owners were very friendly and had everything you could think of, including local trails, equipment to go out on the lake which was included with the cabin games, local eats, etc."
The price is AU$296
includes taxes & fees
14 Mar - 15 Mar
Trout House Village Resort

Walk to Million Dollar Beach from this awesome Cottage!

10.0 out of 10, Exceptional, (151)
"This is our third time staying at this property. Each and every time, I am so sad to leave. The hosts are fantastic and answer promptly any questions we may have. This property is so beautiful and we can't wait to come back again next spring."
Walk to Million Dollar Beach from this awesome Cottage!

Beautiful cottage on quiet country road walking distance to charming North Creek

9.8 out of 10, Exceptional, (36)
"My partner and I had a wonderful visit to the cottage to celebrate his birthday weekend! The cottage was absolutely lovely with so many windows to enjoy the incredible snowy views. The bed was so comfy (that's a must when I'm traveling!), and the fireplace was such a nice, cozy addition. Leslie was very responsive with communication. All in all a wonderful property and host!"
The price is AU$343
includes taxes & fees
25 Mar - 26 Mar
Beautiful cottage on quiet country road walking distance to charming North Creek

Terrace on the Lake, Spectacular Large Home with Private Beach

10.0 out of 10, Exceptional, (305)
"We stayed at Terrace on the Lake with several friends and their families and had a great time! The house was clean and had everything we needed--including space for the kids to play. Since it was winter we also appreciated the proximity to Gore Mountain. "
Terrace on the Lake, Spectacular Large Home with Private Beach

PET-FRIENDLY - Twilight Cabin a Unique Waterfront Log Cabin

9.8 out of 10, Exceptional, (89)
"Excellent cabin, stayed twice now. Well-appointed kitchen easy to cook in. Easy access but feels more remote, on a beautiful road. Really good experience, will go back again."
PET-FRIENDLY - Twilight Cabin a Unique Waterfront Log Cabin

Scenic lakefront retreat with water access, private dock, grill, W/D & fireplace

9.8 out of 10, Exceptional, (12)
"We loved our stay. 67 steps is a fantastic property; quaint, bright, and peaceful. Kitchen was fully equipped, bedrooms were sparkling clean and beautifully furnished, and the house was warm and welcoming. We highly recommend this home."
Scenic lakefront retreat with water access, private dock, grill, W/D & fireplace

Camp Lillian Gorgeous New Cabin with Mountain Views

9.8 out of 10, Exceptional, (65)
"Beautiful little cabin! Rustic, quaint, and comfortable. Would definitely stay again!"
The price is AU$342
includes taxes & fees
12 Mar - 13 Mar
Camp Lillian Gorgeous New Cabin with Mountain Views

Ultimate couples getaway! Quiet and private Lakeside Cottage in the Adirondacks

9.2 out of 10, Wonderful, (50)
"Relaxing, energized. "
Ultimate couples getaway! Quiet and private Lakeside Cottage in the Adirondacks

Adirondack Bungalow Getaway

10.0 out of 10, Exceptional, (49)
"Had a wonderful stay at this property. Owner was friendly and readily available. Easy to get to and good proximity to ski area. "
The price is AU$267
includes taxes & fees
16 Mar - 17 Mar
Adirondack Bungalow Getaway

PET-FRIENDLY - Adirondack Retreat w/ Private Sandy Beach Close To Season Events

9.0 out of 10, Wonderful, (54)
"We rented the main house and guest house for a ski trip with our kids and some of their college friends. Upon arrival, the place was spotless! There was plenty of room for sleeping and hanging out. Guest house was also perfect. Kitchen was well stocked. Gore mountain very close also convenient to supermarket and a few restaurants. Only minor issue was inconsistent water pressure which is not unusual in ski / lake houses like.this. Would definitely rent again "
PET-FRIENDLY - Adirondack Retreat w/ Private Sandy Beach Close To Season Events

Beautiful Log House In Bolton In Lake George Paradise! Dog friendly!

9.2 out of 10, Wonderful, (96)
"The home was amazing plenty of space for the whole family we all had a great stay at the home. The movie selection was great and was nice to unplug for a bit and watch movies with the family. The only problem I had was the road entering home is a bit challenging even with 4x4 the top portion was all ice and made almost impossible to climb but luckily neighbors were great and they had someone come sand within hour which fixed the issue. Will def stay again maybe summer next time if available "
Beautiful Log House In Bolton In Lake George Paradise! Dog friendly!

Ultimate Adirondack Getaway ~ Private Pool and Hot Tub!

10.0 out of 10, Exceptional, (312)
"My Dad had always wanted to spend a Christmas in a log cabin. So, the family and I had decided to book this beautiful home a year in advance. During that time, my Dad was diagnosed with Stage 4 esophageal cancer. He did have the treatable kind with a good prognosis. My Dad went through his 7 weeks of radiation and chemo. Unfortunately, he died in his sleep 2 days after his last day of treatment. My whole family decided that we would honor my fathers wish and spend our Christmas in this home...
Ultimate Adirondack Getaway ~ Private Pool and Hot Tub!

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

10.0 out of 10, Exceptional, (78)
"Love, love, love! No doubt we will be back. My husband and I had the most wonderful experience. The hosts have created such a warm, relaxing, cozy, and beautiful home…perfect for a winter getaway. They are communicative and so helpful with anything you need. Their house is situated privately yet, close enough to activities. "
Private Adirondack Getaway. Stunning Fall Foliage. Close to Lake George and VT.

RESTORED HISTORIC ADIRONDACK CAMP: VIEWS OF NEARBY GORE MOUTAIN, PRIVACY, HISTOR

9.2 out of 10, Wonderful, (57)
"Absolutely love this magical place. Already planning our summer trip!"
The price is AU$384
includes taxes & fees
12 Mar - 13 Mar
RESTORED HISTORIC ADIRONDACK CAMP: VIEWS OF NEARBY GORE MOUTAIN, PRIVACY, HISTOR

PET-FRIENDLY - Wonderfully Situated. A Truly Beautiful Setting.

9.2 out of 10, Wonderful, (25)
"Needs better WiFi Internet signal weak. Connections not available in all rooms"
PET-FRIENDLY - Wonderfully Situated. A Truly Beautiful Setting.

Cozy South Bay Cabin w/ Lake & Mountain Views

9.8 out of 10, Exceptional, (17)
"Amazing piece of property, beautiful views, and direct access to water, Cabin is very clean and offers everything needed for a comfortable stay. A fishermans paradise. Will book again for sure !!"
Cozy South Bay Cabin w/ Lake & Mountain Views
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.
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Other types of properties in Chestertown you may be interested in

Holiday Inn Resort Lake George - Adirondack Area by IHG

3.0 star property
9.2 out of 10, Wonderful, (1002)
"Amazing Staff and super Clean facility ! "
The price is AU$185
includes taxes & fees
8 Apr - 9 Apr
Holiday Inn Resort Lake George - Adirondack Area by IHG

Six Flags Great Escape Lodge & Indoor Waterpark

3.5 star property
7.8 out of 10, Good, (1088)
"It was amazing for the family! Very kid friendly they do activities at night in the lobby for the kids! "
The price is AU$352
includes taxes & fees
13 Mar - 14 Mar
Six Flags Great Escape Lodge & Indoor Waterpark

The Queensbury Hotel

3.0 star property
9.2 out of 10, Wonderful, (1234)
"Beautiful Hotel ,walkig distance to downtown GF. Have to stop in to Fenimores,their cozy bar restaurant "
The price is AU$182
includes taxes & fees
12 Mar - 13 Mar
The Queensbury Hotel
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.

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, Spectacular Large Home with Private Beach: 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 60 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.