Photo by Julie Miller

Chestertown Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Nov 21 - Nov 23
In two months
Jan 2 - Jan 4
In three months
Jan 30 - Feb 1
In four months
Feb 27 - Mar 1

Vacation Rentals in Chestertown

Outdoor dining
The Lily Pad at Loon Lake near Gore Mountain

The Lily Pad at Loon Lake near Gore Mountain

Chestertown
9.6 out of 10, Exceptional, (39)
"We had a great week. The house was clean and well stocked with pots,pans,dishes etc. The beds were comfortable and the linens were high quality. We would definitely recommend the lily pad. "
United States
Deb S.
$400 nightly
The price is $444
Nov 9 - Nov 10
Total with taxes and fees
The Lily Pad at Loon Lake near Gore Mountain
Luxury Cabin, 1 Bedroom, Lake View | Living area | 42-inch Smart TV with digital channels, DVD player, streaming services
Trout House Village Resort

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
$189 nightly
The price is $210
Nov 8 - Nov 9
Total with taxes and fees
Trout House Village Resort
Fridge, microwave, oven, stovetop
Perfect Autumn Getaway!

Perfect Autumn Getaway!

Warrensburg
$212 nightly
The price is $214
Nov 11 - Nov 12
Total with taxes and fees
Perfect Autumn Getaway!
Outdoor dining
Gore Mountain Lift View: North Creek Main St Apt 2

Gore Mountain Lift View: North Creek Main St Apt 2

North Creek
9.0 out of 10, Wonderful, (10)
"Place was great for the price. Clean and was easy to communicate with the owner. "
United States
Amanda N.
$205 nightly
The price is $229
Nov 8 - Nov 9
Total with taxes and fees
Gore Mountain Lift View: North Creek Main St Apt 2
Exterior
Gore Mountain Lift View: Wade St. Apt 2

Gore Mountain Lift View: Wade St. Apt 2

North Creek
9.4 out of 10, Exceptional, (12)
"It's a clean apartment for a short stay. It is not having 4 bedrooms as listed but the place has a lot of beds and sofa to accommodate 6-8 people. The kitchen is limited with no venting hood. We cooked bacon and almost set off the fire alarm. Overall, a good place for the value."
United States
Shaun W.
$205 nightly
The price is $229
Nov 8 - Nov 9
Total with taxes and fees
Gore Mountain Lift View: Wade St. Apt 2
Terrace/patio
Little Black Aframe by the Brook- 5m to Waterfall

Little Black Aframe by the Brook- 5m to Waterfall

Warrensburg
8.8 out of 10, Excellent, (5)
"Looks exactly how it does in the pictures. So cozy and perfect for a little get away. Far away from everything but also close enough to a town if anything is needed! Definitely will be back!"
United States
Tessa R.
$193 nightly
The price is $214
Nov 10 - Nov 11
Total with taxes and fees
Little Black Aframe by the Brook- 5m to Waterfall
Fridge, microwave, oven, stovetop
Perfect Autumn Getaway!

Perfect Autumn Getaway!

Warrensburg
$306 nightly
The price is $310
Nov 9 - Nov 10
Total with taxes and fees
Perfect Autumn Getaway!
Game room
The Office at North Creek All Season Rental

The Office at North Creek All Season Rental

North Creek
9.2 out of 10, Wonderful, (10)
"Endroit très tranquille, nous avons manqués de rien! Communication facile avec les proprios! Merci"
Canada
Mathieu
$206 nightly
The price is $230
Nov 8 - Nov 9
Total with taxes and fees
The Office at North Creek All Season Rental
Interior
ADORABLE NEW CABIN WITH AMAZING MOUNTAIN VIEWS

ADORABLE NEW CABIN WITH AMAZING MOUNTAIN VIEWS

North River
10.0 out of 10, Exceptional, (92)
"The place was perfect for us and exceeded our expectations."
United States
Ronald P.
$246 nightly
The price is $273
Nov 10 - Nov 11
Total with taxes and fees
ADORABLE NEW CABIN WITH AMAZING MOUNTAIN VIEWS
Exterior
Dog friendly lakefront home w/fireplace near Lk George. Telecommuters welcome!

Dog friendly lakefront home w/fireplace near Lk George. Telecommuters welcome!

Fort Ann
10.0 out of 10, Exceptional, (23)
"This is a beautiful property on an idyllic lake which we enjoyed very much. Linda was a more than accommodating host and we enjoyed talking with her and learning about the property and the area. Great water activities, especially the paddle boarding and canoeing. Proximity to Lake George is a plus!"
United States
Lois S.
$353 nightly
The price is $392
Nov 10 - Nov 11
Total with taxes and fees
Dog friendly lakefront home w/fireplace near Lk George. Telecommuters welcome!
Property grounds
Gore Mountain Lift View Ski House: Wade St. 1

Gore Mountain Lift View Ski House: Wade St. 1

North Creek
9.4 out of 10, Exceptional, (19)
"The location near Main St was less than a 10 minute drive to the mountain and everything else was closer or walkable. The unit was clean, safe and ‘as advertised’ Communications was good. We would book again."
United States
Barry W.
$205 nightly
The price is $229
Nov 9 - Nov 10
Total with taxes and fees
Gore Mountain Lift View Ski House: Wade St. 1
1 bedroom, free WiFi, bed sheets
Little Red Cabin by the Brook- 5m to Waterfall

Little Red Cabin by the Brook- 5m to Waterfall

Warrensburg
9.4 out of 10, Exceptional, (19)
"This property is beautiful"
United States
Randy P.
$238 nightly
The price is $264
Nov 9 - Nov 10
Total with taxes and fees
Little Red Cabin by the Brook- 5m to Waterfall
Exterior
Adirondack Bungalow Getaway

Adirondack Bungalow Getaway

Warrensburg
10.0 out of 10, Exceptional, (65)
"Great house!! Very clean!! Short drive to Lake George. Would definitely stay again!!"
United States
Ryan S.
$175 nightly
The price is $194
Nov 9 - Nov 10
Total with taxes and fees
Adirondack Bungalow Getaway
A heated pool
Charming 2-bedroom condo with fitness room, WiFi in Wonderful Lake George

Charming 2-bedroom condo with fitness room, WiFi in Wonderful Lake George

Lake George
10.0 out of 10, Exceptional, (1)
"We had a wonderful two night stay. Enjoyed the Lake and attractions!"
United States
Tatyana A.
$193 nightly
The price is $214
Nov 9 - Nov 10
Total with taxes and fees
Charming 2-bedroom condo with fitness room, WiFi in Wonderful Lake George
House (2 Bedrooms) | Interior
7 Mi to Glens Falls: Peaceful Retreat w/ Game Room

7 Mi to Glens Falls: Peaceful Retreat w/ Game Room

3.0 star property
Hudson Falls
7 Mi to Glens Falls: Peaceful Retreat w/ Game Room
Interior
RESTORED HISTORIC ADIRONDACK CAMP: VIEWS OF NEARBY GORE MOUTAIN, PRIVACY, HISTOR

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

North River
9.2 out of 10, Wonderful, (61)
"Bird Camp is nestled on a beautiful and peaceful hobby farm. The camp is well maintained and very cozy. We had a wonderful time and we are looking forward to our next stay here!"
United States
Zacchary B.
$240 nightly
The price is $266
Nov 8 - Nov 9
Total with taxes and fees
RESTORED HISTORIC ADIRONDACK CAMP: VIEWS OF NEARBY GORE MOUTAIN, PRIVACY, HISTOR
Outdoor dining
Camp Lillian Gorgeous New Cabin with Mountain Views

Camp Lillian Gorgeous New Cabin with Mountain Views

North River
9.8 out of 10, Exceptional, (74)
"Enjoyed our stay. Had everything we needed. Quiet with beautiful view."
United States
steve z.
$212 nightly
The price is $235
Nov 9 - Nov 10
Total with taxes and fees
Camp Lillian Gorgeous New Cabin with Mountain Views
Coffee/tea maker, cookware/dishes/utensils
Cozy Adirondack Cabin Near Lake George w/ Wood Burning Stove & Lake Access

Cozy Adirondack Cabin Near Lake George w/ Wood Burning Stove & Lake Access

Hadley
10.0 out of 10, Exceptional, (21)
"Quant little cabin tucked away. Very nice place to start close to lake George with out ask the hustle and bustle of town."
United States
matthew r.
$204 nightly
The price is $220
Nov 10 - Nov 11
Total with taxes and fees
Cozy Adirondack Cabin Near Lake George w/ Wood Burning Stove & Lake Access
Game room
Gore Mountain Getaway Huge house with 3 Apartments

Gore Mountain Getaway Huge house with 3 Apartments

North Creek
10.0 out of 10, Exceptional, (1)
"We enjoyed a family reunion at your buildings - everyone had a great time. The children loved the game room!"
United States
Jane H W.
$503 nightly
The price is $563
Nov 13 - Nov 14
Total with taxes and fees
Gore Mountain Getaway Huge house with 3 Apartments
Fridge, microwave, oven, stovetop
1-BR Gem Near Downtown & Nature Escapes

1-BR Gem Near Downtown & Nature Escapes

Glens Falls
10.0 out of 10, Exceptional, (1)
"Everything was fantastic, the only thing i would say is that the stairs my be a problem fo older guests. For me I would definatly book again."
United States
george v.
$263 nightly
The price is $276
Nov 10 - Nov 11
Total with taxes and fees
1-BR Gem Near Downtown & Nature Escapes
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.
View all properties
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

Hampton Inn & Suites Lake George

Hampton Inn & Suites Lake George

10/10 Excellent
"Yes"
Kenneth 3-night trip
Posted 3 days ago
Hampton Inn & Suites Lake George

Find out more about Chestertown

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, condos, resorts, cabins, villas, motels. 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 low season months. For more hustle and bustle, you may prefer to visit Chestertown in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $210 per night. Rates vary depending on your travel dates, location, and amenities so make a search and 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.

Explore a world of travel with Expedia

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?

Terrace on the Lake – Private Lakefront with Breathtaking Views: This vacation home rental near Chestertown 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 8 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. It offers a garden, a selection of games, and a hot tub so you can immerse yourself in your vacation.

How many vacation rentals will I find in Chestertown?

With 58 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.