Title: Holiday Rentals Chestertown from £153: Find Short-Term Rentals & Holiday Accommodations | Expedia.co.uk

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## Check prices for these dates

In two weeks

[10 Apr - 12 Apr](https://www.expedia.co.uk/Hotel-Search?regionId=89045&startDate=2026-04-10&endDate=2026-04-12&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In two months

[22 May - 24 May](https://www.expedia.co.uk/Hotel-Search?regionId=89045&startDate=2026-05-22&endDate=2026-05-24&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In three months

[19 Jun - 21 Jun](https://www.expedia.co.uk/Hotel-Search?regionId=89045&startDate=2026-06-19&endDate=2026-06-21&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

In four months

[17 Jul - 19 Jul](https://www.expedia.co.uk/Hotel-Search?regionId=89045&startDate=2026-07-17&endDate=2026-07-19&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&rfrr=TG.LP.CheckPrices.Hotel&openPlayBack=true)

## Our top choices for Chestertown holiday rentals

![Cabin, 1 Bedroom, Non Smoking, Lake View | Egyptian cotton sheets, premium bedding, individually decorated](https://images.trvl-media.com/lodging/109000000/108600000/108598400/108598337/f9b80062.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Front of property](https://images.trvl-media.com/lodging/109000000/108600000/108598400/108598337/ca48d4b5.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Lake](https://images.trvl-media.com/lodging/109000000/108600000/108598400/108598337/c1a259a1.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![Luxury Cabin | Egyptian cotton sheets, premium bedding, individually decorated](https://images.trvl-media.com/lodging/109000000/108600000/108598400/108598337/aef23bb7.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### Trout House Village Resort 

[](https://www.expedia.co.uk/Hague-Hotels-Trout-House-Village-Resort.h108598337.Hotel-Information)

Hague

9.8/10

Exceptional

(22 reviews)

"Great updated cabin. "

![United States](https://a.travel-assets.com/egds/marks/flags/us.svg)

Diane

£198

includes taxes & fees

31 Mar - 1 Apr

[](https://www.expedia.co.uk/Hague-Hotels-Trout-House-Village-Resort.h108598337.Hotel-Information)

![House, 5 Bedrooms | Exterior](https://images.trvl-media.com/lodging/118000000/117330000/117320700/117320619/ba3ba704.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House, 5 Bedrooms | Property grounds](https://images.trvl-media.com/lodging/118000000/117330000/117320700/117320619/448c2500.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House, 5 Bedrooms | Interior](https://images.trvl-media.com/lodging/118000000/117330000/117320700/117320619/c187e462.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

![House, 5 Bedrooms | Interior](https://images.trvl-media.com/lodging/118000000/117330000/117320700/117320619/b23b4821.jpg?impolicy=fcrop&w=357&h=201&p=1&q=medium)

### 10 Mi To Gore Mountain: Home In Adirondack Park 5 Bedroom Home

[](https://www.expedia.co.uk/Olmstedville-Hotels-10-Mi-To-Gore-Mountain-Home-In-Adirondack-Park-5-Bedroom-Home.h117320619.Hotel-Information)

Olmstedville

£609

includes taxes & fees

5 Apr - 6 Apr

[](https://www.expedia.co.uk/Olmstedville-Hotels-10-Mi-To-Gore-Mountain-Home-In-Adirondack-Park-5-Bedroom-Home.h117320619.Hotel-Information)

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](https://expedia.co.uk/Hotel-Search?startDate=2026-04-11&endDate=2026-04-12&regionId=89045&adults=2&categorySearch=vacation_rentals_option&stay_options_group=vacation_rentals_option&openPlayBack=true)

## Find holiday rentals that suit your style

Private holiday homes

[](https://www.expedia.co.uk/Hotel-Search?destination=Chestertown%2C+New+York%2C+United+States+of+America&regionId=89045&latLong=43.652863%2C-73.801254&adults=2&startDate=2026-06-26&d1=2026-06-26&endDate=2026-06-29&d2=2026-06-29&lodging=VACATION_HOME)

Cabins

[](https://www.expedia.co.uk/Hotel-Search?destination=Chestertown%2C+New+York%2C+United+States+of+America&regionId=89045&latLong=43.652863%2C-73.801254&adults=2&startDate=2026-06-26&d1=2026-06-26&endDate=2026-06-29&d2=2026-06-29&lodging=CABIN)

Apartments

[](https://www.expedia.co.uk/Hotel-Search?destination=Chestertown%2C+New+York%2C+United+States+of+America&regionId=89045&latLong=43.652863%2C-73.801254&adults=2&startDate=2026-06-26&d1=2026-06-26&endDate=2026-06-29&d2=2026-06-29&lodging=APARTMENT)

Cottages

[](https://www.expedia.co.uk/Hotel-Search?destination=Chestertown%2C+New+York%2C+United+States+of+America&regionId=89045&latLong=43.652863%2C-73.801254&adults=2&startDate=2026-06-26&d1=2026-06-26&endDate=2026-06-29&d2=2026-06-29&lodging=COTTAGE)

Chalets

[](https://www.expedia.co.uk/Hotel-Search?destination=Chestertown%2C+New+York%2C+United+States+of+America&regionId=89045&latLong=43.652863%2C-73.801254&adults=2&startDate=2026-06-26&d1=2026-06-26&endDate=2026-06-29&d2=2026-06-29&lodging=CHALET)

Condos

[](https://www.expedia.co.uk/Hotel-Search?destination=Chestertown%2C+New+York%2C+United+States+of+America&regionId=89045&latLong=43.652863%2C-73.801254&adults=2&startDate=2026-06-26&d1=2026-06-26&endDate=2026-06-29&d2=2026-06-29&lodging=CONDO)

Villas

[](https://www.expedia.co.uk/Hotel-Search?destination=Chestertown%2C+New+York%2C+United+States+of+America&regionId=89045&latLong=43.652863%2C-73.801254&adults=2&startDate=2026-06-26&d1=2026-06-26&endDate=2026-06-29&d2=2026-06-29&lodging=VILLA)

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## Top Chestertown Hotel Reviews

![Country Inn & Suites by Radisson, Lake George (Queensbury), NY](https://images.trvl-media.com/lodging/2000000/1510000/1503700/1503683/8b1d260e_y.jpg)

### Country Inn & Suites by Radisson, Lake George (Queensbury), NY

10/10 Excellent

"The room was very clean but we were cold. Didn’t want to turn the heat on and listen to the noise. But it would have been nice if the room had an extra blanket. Yes, we could have called down to the front desk but it was late when we went to bed."

[](https://expedia.co.uk/Lake-George-Hotels-Country-Inn-Suites-By-Radisson.h1503683.Hotel-Information)

![The Queensbury Hotel](https://images.trvl-media.com/lodging/1000000/50000/40400/40334/2f07bb66_y.jpg)

### The Queensbury Hotel

10/10 Excellent

"Clean and quiet "

[](https://expedia.co.uk/Lake-George-Hotels-The-Queensbury-Hotel.h40334.Hotel-Information)

![Lakefront townhome on Tripp Lake in the Adirondacks, minutes from Gore Mountain skiing, Lake George, hiking, kayaking, and year-round outdoor adventure.](https://images.trvl-media.com/lodging/121000000/120760000/120755100/120755074/be8d3406_y.jpg)

### Lakefront townhome on Tripp Lake in the Adirondacks, minutes from Gore Mountain skiing, Lake George, hiking, kayaking, and year-round outdoor adventure.

10/10 Excellent

"This was our first vacation rental as we were reluctant to try it after reading horrible stores about hidden fees and a tons of house cleaning list. We took a plunge this time and I am glad we did it. If you cook a lot (not us), a large party (not us), then this is perfect. It was a bit too big for us since we are used to staying at hotels. But it was nice to have a full kitchen (all we did was warming up our prepared food) and have separate space so that we could do our own work. The townhouse is really on a lakefront --We took a short walk the first day. Then we got busy and it was rainy, so we were not able to do it again while we stayed. It is very quiet around here. Luckily we did not see any (scary) wild animals, so it was all good! As city folks, we tend to get worried about seeing 'wild animals". The check-out list was not much, so our view on using vacation rental has changed--that we will probably use vacation rentals more in the future."

[](https://expedia.co.uk/Chestertown-Hotels-Secluded-And-Cozy-Lakeside-Townhome-On-Tripp-Lake.h120755074.Hotel-Information)

![Best Western of Lake George](https://images.trvl-media.com/lodging/1000000/30000/25000/24945/5f75ab9d_y.jpg)

### Best Western of Lake George

4/10 Poor

"Elsie the breakfast person was absolutely top notch. The front desk person was ok. They never cleaned the room in 4 days. The Tub was not cleaned when I showed up. No WiFi. Old, run-down and generally unkempt inside and out. Never again, too many better options around Lake George."

[](https://expedia.co.uk/Lake-George-Hotels-Best-Western-Of-Lake-George.h24945.Hotel-Information)

![Six Flags Great Escape Lodge & Indoor Waterpark](https://images.trvl-media.com/lodging/2000000/1390000/1385500/1385446/fcd6f5d2_y.jpg)

### Six Flags Great Escape Lodge & Indoor Waterpark

2/10 Terrible

"Beds awful microwave didn’t work fridge fridge didn’t work"

[](https://expedia.co.uk/Lake-George-Hotels-Six-Flags-Lodge-Indoor-Waterpark.h1385446.Hotel-Information)

![Lodge at Schroon Lake](https://images.trvl-media.com/lodging/93000000/92470000/92467000/92466918/12893ba7_y.jpg)

### Lodge at Schroon Lake

10/10 Excellent

"The staff was outstanding, at the registration desk, at the Bevy restaurant for breakfast, and at the Brown Swan for dinner. We will be going back for sure."

[](https://expedia.co.uk/Schroon-Lake-Hotels-Lodge-At-Schroon-Lake.h92466918.Hotel-Information)

![Hampton Inn & Suites Lake George](https://images.trvl-media.com/lodging/2000000/1510000/1503800/1503711/7a626a12_y.jpg)

### Hampton Inn & Suites Lake George

8/10 Good

"The room was clean and they welcomed my small dog. I know it was off season but I booked this place cause it had a lounge area but that was not available all weekend . The ice machine didn’t work on floor 2 . It was a nice place. "

[](https://expedia.co.uk/Lake-George-Hotels-Hampton-Inn-Suites-Lake-George.h1503711.Hotel-Information)

![Fort William Henry Hotel and Conference Center](https://images.trvl-media.com/lodging/2000000/1130000/1129600/1129524/8b8d1fb3_y.jpg)

### Fort William Henry Hotel and Conference Center

8/10 Good

"The room I was assigned had not been cleaned well, phone didn't work, and the window was broken. I went to the front desk and was immediately assigned a different room. The rest of my stay was great."

[](https://expedia.co.uk/Lake-George-Hotels-Fort-William-Henry-Hotel-And-Conference-Center.h1129524.Hotel-Information)

![La Quinta Inn & Suites by Wyndham Lake George](https://images.trvl-media.com/lodging/83000000/82500000/82499900/82499882/85a37759_y.jpg)

### La Quinta Inn & Suites by Wyndham Lake George

10/10 Excellent

"Room was very nice!"

[](https://expedia.co.uk/Lake-George-Hotels-The-George-NY.h82499882.Hotel-Information)

## 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](https://www.expedia.co.uk/aa/Apartments), cottages, [apart-hotels](https://www.expedia.co.uk/aa/ApartHotels), cabins, [villas](https://www.expedia.co.uk/aa/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 £153 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. 

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## Frequently asked questions

### Can I find holiday rentals in Chestertown?

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

### How many holiday rentals will I find in Chestertown?

### What’s there to see and do in Chestertown?

### What’s a holiday rental in Chestertown like?

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