Hot Chestertown Cottage Rates

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Featured Cottages in Chestertown

Private Cottage on Lake George W/ Wood-Burning Fireplace, Lake View, & Fast WiFi

Private Cottage on Lake George W/ Wood-Burning Fireplace, Lake View, & Fast WiFi

Queensbury NY
With a stay at this cottage in Lake George, you'll be a 1-minute drive from Lake George and 7 minutes from Dark Bay.
Opens in a new windowPrivate Cottage on Lake George W/ Wood-Burning Fireplace, Lake View, & Fast WiFi
Beautiful lakeview cottage on Friends Lake

Beautiful lakeview cottage on Friends Lake

Chestertown NY
Located in Chestertown, this cottage is on a lake, a 1-minute drive from Friends Lake and 8 minutes from Loon Lake.
Opens in a new windowBeautiful lakeview cottage on Friends Lake
Walk to Million Dollar Beach from this awesome Cottage!

Walk to Million Dollar Beach from this awesome Cottage!

Lake George NY
When you stay at this cottage in Lake George, you'll be on a lake, a 1-minute drive from Lake George and 8 minutes from Six Flags Great Escape.
Opens in a new windowWalk to Million Dollar Beach from this awesome Cottage!
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 Dog friendly lakefront home w/fireplace near Lk George. Telecommuters welcome!

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

Fort Ann NY
The price is AU$581 per night from 21 Dec to 22 Dec
AU$581
21 Dec - 22 Dec
includes taxes & fees
When you stay at this cottage in Fort Ann, you'll be on the waterfront, within a 10-minute walk of Lake Hadlock and Hadlock Pond.
Opens in a new window Dog friendly lakefront home w/fireplace near Lk George. Telecommuters welcome!
9 Mi to Lake George Village: Home in Queensbury

9 Mi to Lake George Village: Home in Queensbury

3 out of 5
Queensbury NY
Located in Queensbury, this cottage is within a 15-minute drive of Six Flags Great Escape and Lake George.
Opens in a new window9 Mi to Lake George Village: Home in Queensbury
Beautiful cottage on quiet country road walking distance to charming North Creek

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

North Creek NY
The price is AU$375 per night from 15 Jan to 16 Jan
AU$375
15 Jan - 16 Jan 2026
includes taxes & fees
With a stay at this cottage in North Creek, you'll be on the waterfront, within a 10-minute drive of Gore Mountain Ski Resort and Hudson River.
Opens in a new windowBeautiful cottage on quiet country road walking distance to charming North Creek
Charming cottage with a cozy, welcoming vibe

Charming cottage with a cozy, welcoming vibe

Bolton Landing NY
When you stay at this cottage in Bolton Landing, you'll be in the mountains, just a 3-minute walk from Lake George and 14 minutes by foot from The Sembrich.
Opens in a new windowCharming cottage with a cozy, welcoming vibe
Hand-Crafted Cottage near Gore Mountain and Minerva Lake

Hand-Crafted Cottage near Gore Mountain and Minerva Lake

Olmstedville NY
When you stay at this cottage in Olmstedville, you'll be 7 minutes by car from Minerva Lake.
Opens in a new windowHand-Crafted Cottage near Gore Mountain and Minerva Lake
Cozy Cottage at Lake George Campsites!

Cozy Cottage at Lake George Campsites!

Queensbury NY
With a stay at this cottage in Queensbury, you'll be a 2-minute drive from Six Flags Great Escape and 9 minutes from Lake George.
Opens in a new windowCozy Cottage at Lake George Campsites!
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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.

Chestertown Budget-Friendly Cottage Accommodation

Adulting can be rough. You love your job, and your sweetheart is the best, but next time someone says “think outside the box” or “we’ll park that”, you just might throw a fit. When was the last time you had one of those really deep convos with your person, anyway? It sounds like you need a holiday, and you’ve come to the right place. Budget-friendly cottage accommodation in Chestertown will have you feeling like your SO is the peanut butter to your jelly again in no time.

We’re not here to tell you what you want—we think you already know. You want a spot that’s totally relaxing, but still has plenty of things to do, you know, if you feel like it. You want great scenery, and you want food that’s worthy of your number one hashtag: #nomnom. Cottage getaways to Chestertown definitely fit the bill.

Yes, the scenery is stunning, but on a romantic cottage holiday, it’s what’s inside that counts. Today’s cottages are filled with those little touches of luxury, like fine bath amenities and gourmet kitchens. You know the saying about how the way to someone’s heart is through their stomach? Don’t miss your chance to impress this holiday—even if that just means remembering their favourite wine. (Hey, that still counts!)

Before you can check out entirely, you’ve got a few last bits of adulting to take care of: pick your perfect cheap country cottage in Chestertown, then type up that email to your boss and request your annual leave. We’re sure they’ll understand.

Chestertown Cottages essential information

Accommodation
159 Cottages
Lowest Price
AU$375
Highest Price
AU$581
Popular accommodation
Private Cottage on Lake George W/ Wood-Burning Fireplace, Lake View, & Fast WiFi, Beautiful lakeview cottage on Friends Lake, Walk to Million Dollar Beach from this awesome Cottage!, Dog friendly lakefront home w/fireplace near Lk George. Telecommuters welcome!, 9 Mi to Lake George Village: Home in Queensbury, Beautiful cottage on quiet country road walking distance to charming North Creek, Charming cottage with a cozy, welcoming vibe, Hand-Crafted Cottage near Gore Mountain and Minerva Lake, Cozy Cottage at Lake George Campsites!

Top trending hotels in Chestertown

Pine Tree Motel & Cabins

Pine Tree Motel & Cabins

2 out of 5
5537 State Route 8 Chestertown NY
When you stay at Pine Tree Motel & Cabins in Chestertown, you'll be in a national park, within a 15-minute walk of Loon Lake and Loon Lake Beach.
Opens in a new windowPine Tree Motel & Cabins
Friends Lake Inn

Friends Lake Inn

4 out of 5
963 Friends Lake Rd Chestertown NY
With a stay at Friends Lake Inn in Chestertown, you'll be near ski lifts, a 4-minute walk from Friends Lake and a 4-minute drive from Loon Lake Beach.
Opens in a new windowFriends Lake Inn
The Fern Lodge

The Fern Lodge

3.5 out of 5
46 Fiddlehead Bay Rd. Chestertown NY
Located in Chestertown, The Fern Lodge is on a lake, a 1-minute drive from Friends Lake and 8 minutes from Loon Lake Beach.
Opens in a new windowThe Fern Lodge
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Six Flags Great Escape Lodge & Indoor Waterpark

Six Flags Great Escape Lodge & Indoor Waterpark

3.5 out of 5
89 Six Flags Dr Queensbury NY
The price is AU$406 per night from 22 Dec to 23 Dec
AU$406
22 Dec - 23 Dec
includes taxes & fees
Located in Queensbury, Six Flags Great Escape Lodge & Indoor Waterpark is in the mountains, within a 5-minute drive of Six Flags Great Escape and Outlets at ...
Opens in a new windowSix Flags Great Escape Lodge & Indoor Waterpark
Don't see what you're looking for?
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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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^Subject to availability and chosen travel dates.