Chestertown Holiday Homes from £135: Search Holiday Homes in Chestertown

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Our top choices for Chestertown holiday 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.

includes taxes & fees

15 Nov - 16 Nov

A compact kitchen with white cabinets, a stainless steel refrigerator, a microwave, a dishwasher, and a coffee maker.

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

Warrensburg

Matthew L.

includes taxes & fees

15 Nov - 16 Nov

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.

includes taxes & fees

15 Nov - 16 Nov

A single-story building with a red door and a garage door.

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

North Creek

Tara F.

includes taxes & fees

1 Dec - 2 Dec

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

North Creek

joseph

includes taxes & fees

15 Nov - 16 Nov

A compact living space with a wooden ceiling, a sofa, a dining table, and a TV mounted on the wall.

6. The Office at North Creek All Season Rental

North Creek

Brandon A.

includes taxes & fees

15 Nov - 16 Nov

A sign for 'Ski Bowl Park' with illuminated tree decorations.

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

Johnsburg

thomas c.

includes taxes & fees

17 Nov - 18 Nov

A spacious room with a high ceiling and large windows offering a mountain view.

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

North Creek

Anne R.

includes taxes & fees

29 Nov - 30 Nov

A log cabin interior with a fireplace, leather seating, and a ceiling fan.

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

Brant Lake

includes taxes & fees

16 Nov - 17 Nov

A spacious yurt interior with a wooden dining area, a kitchen with cabinets, and a birch tree.

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

Minerva

Christine T.

includes taxes & fees

15 Nov - 16 Nov

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.

includes taxes & fees

16 Nov - 17 Nov

A wooden room with two large circular windows, a blue floor, and a wooden bench.

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

North River

Dave C.

includes taxes & fees

16 Nov - 17 Nov

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

North Creek

Jane H W.

includes taxes & fees

22 Nov - 23 Nov

A spacious living area with a wooden ceiling, a sofa set, a coffee table, and a fireplace.

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

Lake Luzerene

Ryen H.

includes taxes & fees

29 Nov - 30 Nov

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.

includes taxes & fees

15 Nov - 16 Nov

A dining area with a large table, chairs, and a view of autumn trees through large windows.

16. Luxurious Lake George Getaway

Lake George

Jennifer H.

includes taxes & fees

22 Nov - 23 Nov

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.

includes taxes & fees

20 Nov - 21 Nov

A modern kitchen with a large window, two bar stools, and a chandelier.

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

Lake George

includes taxes & fees

18 Nov - 19 Nov

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

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 Holiday Homes information

Number of reviews	285
Accommodation	549 Holiday Homes
Lowest Price	£135
Highest Price	£1,441

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Check prices for these dates

Our top choices for Chestertown holiday 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

15. Copeland Cabin - Charming Lake House in the Adirondacks

16. Luxurious Lake George Getaway

17. Cozy 3 bedroom house

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

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

Find holiday 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 Holiday Homes information

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