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Chestertown Holiday Rentals

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Holiday Rentals in Chestertown

Eagles Nest at Loon Lake near Gore Mountain

Chestertown
10.0 out of 10, Exceptional, (113)
"This is the second time that our family has stayed at Eagle's Nest. We enjoyed our time together once again. We had plenty of room and the fire pit, game room and games, sand box and canoes/kayaks were a welcome addition once again. We love the area and this home accommodates our family nicely."
United States
Pam R.
Eagles Nest at Loon Lake near Gore Mountain

Elizabeth. A Guest House Near Lake George.

Chestertown
8.2 out of 10, Very good, (45)
"The house was beautiful and charming and plenty of space. We have no complaints but recommend hand towels in the bathrooms. Probably will look up this place again for a skiing trip this winter."
United States
Dennis M Wilson J.
Elizabeth. A Guest House Near Lake George.

Lincoln Log Colony

2.0 star property
Lake George
8.8 out of 10, Excellent, (10)
"The cabin was clean and ready when arrived. Corrina went above and beyond to make us feel welcome. We are ready to go back soon."
United States
Lynn
Lincoln Log Colony

Waterfront Home on Lake George w/ Boat Dock!

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

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

Lake George
9.0 out of 10, Wonderful, (20)
"Wonderful house on the lake! Perfect location. Lovely beach. Really felt at home."
United States
Alison K.
Cozy, pet friendly, newly renovated chalet home with shared beach & water views

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

Warrensburg
9.8 out of 10, Exceptional, (191)
"We had an unforgettable stay that truly elevated our entire vacation experience.The stay was absolutely fantastic, one of the best places we’ve ever stayedThis property has all the amenities required for a great vacation...its a flawless propertyIf anybody visiting Lake George, I would recommend this property 100%Thank you."
United States
nanda k.
ADK Riverside Retreat-Heated Pool-Hot Tub- close to Lake George and Gore

ADORABLE NEW CABIN WITH AMAZING MOUNTAIN VIEWS

North River
10.0 out of 10, Exceptional, (93)
"Great location beautiful view and very nice cabin thank you!"
United States
Aline B.
The price is AU$334
includes taxes & fees
30 Nov - 1 Dec
ADORABLE NEW CABIN WITH AMAZING MOUNTAIN VIEWS

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

Warrensburg
10.0 out of 10, Exceptional, (169)
"Property was wonderful, so great to have a wonderful pool and hot tub. The playground was loved by our grandchildren. The house had everything anyone would need. Highly recommend."
United States
Alana K.
luxury log home mins from Lake George, w/ heated salt water pool!

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!

Adirondack Bungalow Getaway

Warrensburg
10.0 out of 10, Exceptional, (67)
"This property is quaint and comfy. It was easy to find and get to places we visited with ease. The neighborhood is quiet. The host Laney is responsive and very nice! We hope to return next year!"
United States
Kathy S.
The price is AU$300
includes taxes & fees
30 Nov - 1 Dec
Adirondack Bungalow Getaway

Hickory Hill Mountaintop charming family friendly quiet very private lake view

Bolton Landing
10.0 out of 10, Exceptional, (141)
"Very nice home, relaxing. "
United States
Stephen C.
Hickory Hill Mountaintop charming family friendly quiet very private lake view

COZY CUB CABIN Brookside • Lake George, Hot Tub, 24 acres w/ Brook

Hague
10.0 out of 10, Exceptional, (42)
"Cozy cabin, close to great hikes."
United States
Melissa L.
COZY CUB CABIN Brookside • Lake George, Hot Tub, 24 acres w/ Brook

Trout House Village Resort

3.0 star property
Hague
9.8 out of 10, Exceptional, (18)
"Very friendly owner and beautiful views"
United States
Anthony
The price is AU$292
includes taxes & fees
30 Nov - 1 Dec
Trout House Village Resort

Lake George Water Front Cabin Spectacular Views

Ticonderoga
9.6 out of 10, Exceptional, (35)
"The house was perfect for my family! The teens loved kayaking! The view was absolutely stunning! Wish we could have stayed longer! Will stay again next year!"
United States
Jillian B.
The price is AU$1,743
includes taxes & fees
30 Nov - 1 Dec
Lake George Water Front Cabin Spectacular Views

Family Friendly - Pet Friendly

Lake George
9.8 out of 10, Exceptional, (68)
"Beautiful home in a great location"
United States
Savannah A.
Family Friendly - Pet Friendly

Lake George,Lakefront,Sleeps 20, 3-homes, 8 bedrooms, lakefront deck, boat avail

Kattskill Bay
10.0 out of 10, Exceptional, (95)
"We had an awesome week of great weather. There was more than enough room for our family of 13 adults and 2 babies and every house was fully equipped in the kitchens. The lake is so clean and beautiful and the set up of the docks is perfect. The sunsets were amazing. Deb was so helpful and very quick to respond to us when we needed something. Would return next year."
United States
Janice F.
Lake George,Lakefront,Sleeps 20, 3-homes, 8 bedrooms, lakefront deck, boat avail

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

Terrace on the Lake – Private Lakefront with Breathtaking Views

Warrensburg
10.0 out of 10, Exceptional, (331)
"Has everything a large group or family needs, and is clean and well maintained"
United States
Bob M.
Terrace on the Lake – Private Lakefront with Breathtaking Views

Ultimate Adirondack Getaway ~ Private Pool and Hot Tub!

Warrensburg
9.8 out of 10, Exceptional, (336)
"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!

Private Adirondack Getaway. Close to Lake George and VT for winter activities.

Clemons
10.0 out of 10, Exceptional, (100)
"We had the best time! The hosts were responsive and they made our stay so enjoyable. We would definitely come again!"
United States
Leah B.
Private Adirondack Getaway. Close to Lake George and VT for winter activities.
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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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, 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 favourite 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 depend 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 AU$292 per night. Entering your travel dates in the search wizard might find you 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.