Chestertown, NY Cottage Rentals from $258

A waterfront town with a pier, dock, and several buildings.

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Our top choices for Chestertown cottages

A small cabin with a red roof, surrounded by trees and a body of water.

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

North Creek

Tim T.

$232 nightly

Nov 20 - Nov 21

Total with taxes and fees

A wooden deck with a view of a lake surrounded by trees.

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

Fort Ann

Robert H.

$381 nightly

Nov 15 - Nov 16

Total with taxes and fees

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Top Chestertown Hotel Reviews

Courtyard by Marriott Lake George

8/10 Good

"The staff was very pleasant and helpful. The food was amazing. The room was very comfortable and nice. I would stay there again. I think this might be my new go to hotel when I visit Lake George."

Friends Lake Inn

10/10 Excellent

"Such a nice place to stay at definitely want to stay there again. Me and my husband went for our honeymoon and the room was super nice and the staff was nice and helpful when we had questions also about the area. The free breakfast that was included was also super delicious. If ur looking for a cozy hotel to stay in at chestertown in the Adirondacks friends lake inn is the go to place."

La Quinta Inn & Suites by Wyndham Lake George

8/10 Good

"Pros: Convenient Location, Good Value, Good Breakfast, Comfortable Beds, Good A/C, Fridge in Room Cons: Carpet (Both Inside and Outside Guest Room) Needs a Deep Clean, Broken Ice Machine Pro and Con: Pool Is Attractive Amenity for Families with Children BUT Unsupervised Children Were Noisy Late Into the Evening."

Holiday Inn Resort Lake George - Adirondack Area by IHG

10/10 Excellent

"Staff from TR's bar treat you like friends and family. All staff at the hotel were very attentive and pleasant. Cleanliness was good. Prices were higher than expected for a holiday in, but the world is getting too expensive. Great stay for the week."

Lodge at Schroon Lake

8/10 Good

"The property was absolutely gorgeous! Unfortunately, the weather didn't cooperate, so we weren't able to enjoy all the amenities as much as we would have liked. We really appreciated being allowed to check in early, especially after driving five hours! There were a few things that could use some improvement. Housekeeping could pay a little more attention to the small details, like making sure there are cups available for the coffee. The rooms could also benefit from better lighting and a little more functional space, as the desk was quite small. I was also disappointed that some sort of complimentary breakfast wasn't offered, even something simple. The restaurant food was delicious, and the drinks were amazing! However, the prices were a bit high for the portion sizes, and the limited menu didn't leave many options. Overall, it's a beautiful property with a lot to offer. A few small improvements would really elevate the experience. We'd love to come back when the weather is nicer and enjoy everything we missed!"

Elizabeth. 15 minutes to Lake George. Seasonal Heated Pool.

10/10 Excellent

"The property is immense! We ended up being 7 adults and 6 children and there was no problem with sleeping/playing space. The pool is immaculately maintained. Although there were a couple of bumps in the road, the owner and staff were quick to remedy. I particularly enjoyed the screened in porch! A true pleasure for a gal not into dealing with the negative parts of nature, i.e. bugs, bees, etc.! I would heartily recommend this property for fun loving families...with a shout out to The Remington Restaurant who accomodated our large family with wonderful food and drink!"

Find out more about Chestertown

Chestertown Cottages information

Number of reviews	93
Accommodation	198 Cottages
Lowest Price	$258
Highest Price	$423

Frequently asked questions

How much do cottages in Chestertown cost?

Prices for cottages in Chestertown range between $258 and $423 per night. Whatever your budget, you're sure to find the perfect place to immerse yourself in nature. These prices were available on Expedia within the past 7 days, for a hotel booking with a check-in date within the next year. Prices reflect current offers and availability is subject to change. Additional terms may apply.

How many cottages are there in Chestertown?

You can choose from 198 cottages in Chestertown. No matter if you're traveling with the little ones or planning a weekend break with close friends, Expedia can help you find the ideal property to reconnect with nature.

Are there any family-friendly cottages in Chestertown?

If you want to slow the pace down a notch in Chestertown, make a booking for the crew at Sunset Mountain Lodge. With a 3-star rating and conveniences like a playground and WiFi, you'll have no trouble settling in at this family-friendly cottage. After checking in and kicking back together in your cozy digs, it's time to head out and discover the local sights. Natural Stone Bridge and Caves and Loon Lake Beach are top family-friendly attractions in Chestertown.

Why book your cottage in Chestertown with Expedia?

Booking a cottage in Chestertown is as simple as entering your travel dates and picking your ideal place for a vacation in the outdoors. From chic retreats to budget-friendly stays and cottages that have perks like free WiFi, Expedia has something for all tastes. As for terrific deals? We've got them as well!

How can I find cheap cottages in Chestertown?

The easiest way to score cheap cottages in Chestertown is with Expedia's handy filter tool. Tailor your search results by amenities, budget and star rating to secure unbeatable prices in just a few keystrokes.

What is there to do in Chestertown near my cottage?

If you want to make the most of your time in Chestertown, make your way to Loon Lake Beach. It's popular among visitors and locals alike.

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Things to do in Lake George

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Our top choices for Chestertown cottages

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

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

Find vacation rentals that suit your style

Top Chestertown Hotel Reviews

Courtyard by Marriott Lake George

The Queensbury Hotel

Friends Lake Inn

Surfside On The Lake

La Quinta Inn & Suites by Wyndham Lake George

Holiday Inn Resort Lake George - Adirondack Area by IHG

Lodge at Schroon Lake

Elizabeth. 15 minutes to Lake George. Seasonal Heated Pool.

Find out more about Chestertown

Chestertown Cottages information

Frequently asked questions

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Search Chestertown Cottages

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OneKeyCash

Upfront pricing

Check prices for these dates

Our top choices for Chestertown cottages

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

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

Find vacation rentals that suit your style

Top Chestertown Hotel Reviews

Courtyard by Marriott Lake George

Find out more about Chestertown

Chestertown Cottages information

Frequently asked questions

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