Chestertown Vacation Home Rentals from CA $252: Search Top Private Vacation Homes for Rent

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Our top choices for Chestertown vacation homes

Pair your adventure with the comfort of our cozy vacation rental, and create memories filled with the flavors of the Adirondacks. Cheers to local taste and timeless relaxation!

1. The Lily Pad at Loon Lake near Gore Mountain

Chestertown

Sara Beth E.

CA $597 total

includes taxes & fees

Nov 15 - Nov 16

A kitchen with a stainless steel sink, a microwave, a coffee maker, and a toaster.

2. Gore MTN & Saratoga ADK Crash Pad! The Cocoon

Warrensburg

Matthew L.

CA $252 total

includes taxes & fees

Nov 15 - Nov 16

A wooden cabin with a porch, wooden furniture, and a view of a forest.

3. Lovely 3-bedroom house close to Gore Mountain for skiing.

North Creek

Renee B.

CA $453 total

includes taxes & fees

Nov 14 - Nov 15

A red door with a geometric dog design and a doorbell.

4. Adirondack Retreat Walk to Gore, Main St, Ski Bowl | Fast WiFi | Sleeps 6

North Creek

Tara F.

CA $366 total

includes taxes & fees

Dec 1 - Dec 2

A covered porch with a red door, two rocking chairs, and a view of the street.

5. Spacious 3BR Walk to Gore & Main St | Game Room, Porch, Fast WiFi | Sleeps 8

North Creek

joseph

CA $339 total

includes taxes & fees

Nov 22 - Nov 23

A room with a pool table, a bar area, and a gaming machine.

6. The Office at North Creek All Season Rental

North Creek

Brandon A.

CA $352 total

includes taxes & fees

Nov 22 - Nov 23

A porch with green railings and red rocking chairs.

7. Adirondack Cabin near Gore Mtn & Lake George, Games, Fire Pit, Sleeps 10, Pets

Johnsburg

thomas c.

CA $327 total

includes taxes & fees

Nov 17 - Nov 18

A cabin with a deck, large windows, and a view of the surrounding landscape.

8. Gore Mountain Views | Luxury Lodge for 12 | Pets

North Creek

Anne R.

CA $1,628 total

includes taxes & fees

Nov 29 - Nov 30

A lakeside view with a grassy area, a small structure, and a tree.

9. Brant Lake Retreat–Sleeps 25 | Hot Tub | Gore Mtn.

Brant Lake

CA $2,753 total

includes taxes & fees

Nov 30 - Dec 1

A picnic table by a calm body of water with a sunset in the background.

10. Redarrow rustic yurt in the Adirondacks, Gore Mt. 15 mins, jug water supplied

Minerva

Christine T.

CA $367 total

includes taxes & fees

Dec 1 - Dec 2

A hot tub in a room with wooden walls, two potted plants, and a clock on the wall.

11. Adirondack Victorian Vacations and Wedding Venue

North Creek

Blair G.

CA $859 total

includes taxes & fees

Nov 30 - Dec 1

A grassy field with a bench and a picnic table, surrounded by trees and a mountain in the distance.

12. Sweet New Cabin With Amazing Views Of The Hudson River

North River

Dave C.

CA $361 total

includes taxes & fees

Nov 16 - Nov 17

13. 6BR Downtown Duplex Walk to Gore & Main St | Porches, Game Room | Sleeps 12

North Creek

Jane H W.

CA $619 total

includes taxes & fees

Nov 22 - Nov 23

A spacious kitchen with wooden ceiling and large windows, a dining area with a wooden table, and a living room with a sofa and TV.

14. Entire Main House w/ Hot Tub | Separate from Basement Apt | No Shared Spaces

Lake Luzerene

Ryen H.

CA $671 total

includes taxes & fees

Nov 29 - Nov 30

A fire pit with Adirondack chairs in a forested area with a lake view.

15. Copeland Cabin - Charming Lake House in the Adirondacks

Fort Ann

Halley S.

CA $982 total

includes taxes & fees

Nov 15 - Nov 16

A swimming pool with wooden walls and large windows.

16. Luxurious Lake George Getaway

Lake George

Jennifer H.

CA $1,192 total

includes taxes & fees

Nov 22 - Nov 23

A modern living room with a flat-screen TV, a black entertainment unit, and a 'Welcome to our home' sign.

17. Cozy 3 bedroom house

South Glens Falls

Gilison D.

CA $437 total

includes taxes & fees

Nov 20 - Nov 21

A modern two-story house with a covered patio and a stone retaining wall.

18. Luxury 3-Bedroom Townhome with Bonus Room in Charming Lake George, Sleeps 8

Lake George

CA $929 total

includes taxes & fees

Nov 17 - Nov 18

A wooden deck with chairs and a view of a lake.

19. Waterfront paradise, hot tub. Saratoga/Lake George. Super clean & sanitized.

Corinth

Sarah G.

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Top Chestertown Hotel Reviews

The Queensbury Hotel

10/10 Excellent

"I really love this hotel. This was our second stay. I love the history that they have preserved."

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 Vacation Homes information

Number of reviews	285
Accommodation	557 Vacation Homes
Lowest Price	CA $252
Highest Price	CA $2,753

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Check prices for these dates

Our top choices for Chestertown vacation homes

1. The Lily Pad at Loon Lake near Gore Mountain

2. Gore MTN & Saratoga ADK Crash Pad! The Cocoon

3. Lovely 3-bedroom house close to Gore Mountain for skiing.

4. Adirondack Retreat Walk to Gore, Main St, Ski Bowl | Fast WiFi | Sleeps 6

5. Spacious 3BR Walk to Gore & Main St | Game Room, Porch, Fast WiFi | Sleeps 8

6. The Office at North Creek All Season Rental

7. Adirondack Cabin near Gore Mtn & Lake George, Games, Fire Pit, Sleeps 10, Pets

8. Gore Mountain Views | Luxury Lodge for 12 | Pets

9. Brant Lake Retreat–Sleeps 25 | Hot Tub | Gore Mtn.

10. Redarrow rustic yurt in the Adirondacks, Gore Mt. 15 mins, jug water supplied

11. Adirondack Victorian Vacations and Wedding Venue

12. Sweet New Cabin With Amazing Views Of The Hudson River

13. 6BR Downtown Duplex Walk to Gore & Main St | Porches, Game Room | Sleeps 12

14. Entire Main House w/ Hot Tub | Separate from Basement Apt | No Shared Spaces