Chestertown Vacation Rentals from AED 634: Search Short-Term Rentals

Q: Can I find vacation rentals in Chestertown?

Yes, we give you a choice of vacation rentals near well known points of interest in Chestertown, or you can choose a more remote option if you want a relaxing place to stay. Nature enthusiasts will enjoy the lakeside in Chestertown. Make sure you have time to check out the coffeehouses and forests during your trip.

Q: What are some of the best vacation home rentals in Chestertown?

Elizabeth. 15 minutes to Lake George.Seasonal Heated Pool. : This highly rated vacation home rental in Chestertown is located on the waterfront and has an outdoor pool, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games. Our travelers also rate Eagles Nest at Loon Lake near Gore Mountain as a favorite home for rent in Chestertown.

Q: How many vacation rentals will I find in Chestertown?

With 62 Expedia vacation rentals, you're sure to find just the right place for your Chestertown stay.

Q: What’s there to see and do in Chestertown?

Loon Lake Beach and Friends Lake are a couple of lovely local spots to get outside and enjoy nature. Loon Lake and Hudson River are other places to visit while you're in town.

Q: What’s a vacation rental in Chestertown like?

Vacation rentals are private properties you can book for a couple of days or more in Chestertown. Vacation rentals provide amenities like kitchens and laundry facilities so you'll have everything you want. If you're concerned about a clean environment, a vacation rental can provide a sense of security away from shared hotel elevators and busy lobbies while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular option for a small group gathering.

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Our top choices for Chestertown vacation rentals

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.

AED 1,549 total

includes taxes & fees

5 Nov - 6 Nov

A log cabin interior with a stone fireplace, wooden ceiling beams, and a large leather sofa.

2. Authentic Log Cabin with Lake Views and Sauna

Chestertown

Joe F.

AED 1,199 total

includes taxes & fees

5 Nov - 6 Nov

A spacious living area with a leather sofa, wooden ceiling, and large windows.

3. 2BR+Loft Cabin—Summer Getaway with Patio,Firepit Near Lake George &Gore Mountain

Warrensburg

Teresa B.

AED 2,033 total

includes taxes & fees

6 Nov - 7 Nov

A two-story building with a balcony and a flag.

4. Penthouse w/ Best Mtn Views Walk to Gore, Main St | Fast WiFi | Sleeps 6

North Creek

Michael

AED 794 total

includes taxes & fees

5 Nov - 6 Nov

A covered porch with a table and chairs, overlooking a residential area with houses and a street.

5. Gore Mountain Lift View: North Creek Main St Apt 2

North Creek

Lynda N.

AED 870 total

includes taxes & fees

5 Nov - 6 Nov

A room with a large window overlooking a forested area, a wooden table with a vase of flowers, and a chair.

6. Secluded Adirondack Chalet/7 mins to Gore Mountain/ Fire pit/Fast Wi-Fi.

North Creek

Linda D.

AED 1,060 total

includes taxes & fees

16 Nov - 17 Nov

A two-story log cabin with a stone foundation, a balcony with outdoor seating, and a garage.

7. Gore Mountain Views | Luxury Escape for 2–4 • Pets

North Creek

AED 1,908 total

includes taxes & fees

8 Nov - 9 Nov

A lakeside cabin with a wooden deck and a view of the lake.

8. Trout House Village Resort

Hague

Matthew

AED 634 total

includes taxes & fees

5 Nov - 6 Nov

9. Luxury Retreat | Near Gore Mountain | Pets

North Creek

AED 2,006 total

includes taxes & fees

9 Nov - 10 Nov

A landscaped garden with a fountain, flags, and a view of a body of water.

10. Walk to Schroon Lake! Studio w/ Shared Fire Pit

Schroon Lake

Adam

AED 624 total

includes taxes & fees

5 Nov - 6 Nov

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

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

North Creek

Renee B.

AED 1,321 total

includes taxes & fees

11 Nov - 12 Nov

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

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

North Creek

Tara F.

AED 934 total

includes taxes & fees

30 Nov - 1 Dec

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

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

Warrensburg

Matthew L.

AED 641 total

includes taxes & fees

10 Nov - 11 Nov

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

North Creek

joseph

AED 912 total

includes taxes & fees

5 Nov - 6 Nov

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

15. The Office at North Creek All Season Rental

North Creek

Brandon A.

AED 947 total

includes taxes & fees

5 Nov - 6 Nov

A small cabin with a red roof and green trim, surrounded by a natural landscape with large rocks and flowering plants.

16. Camp RiverWood on the Hudson River

North Creek

Paul N.

AED 885 total

includes taxes & fees

5 Nov - 6 Nov

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

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

North Creek

Tim T.

AED 950 total

includes taxes & fees

5 Nov - 6 Nov

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

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

North Creek

Anne R.

AED 3,567 total

includes taxes & fees

9 Nov - 10 Nov

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

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

Brant Lake

AED 7,140 total

includes taxes & fees

5 Nov - 6 Nov

A sandy beach with a calm lake, trees, and a distant hill.

20. Schroon Lake Room < 1 Mi to Marina & Beach!

Schroon Lake

Kevin

AED 624 total

includes taxes & fees

5 Nov - 6 Nov

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Top Chestertown Hotel Reviews

Fort William Henry Hotel and Conference Center

10/10 Excellent

"Great location"

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!"

Frequently asked questions

Can I find vacation rentals in Chestertown?

Yes, we give you a choice of vacation rentals near well known points of interest in Chestertown, or you can choose a more remote option if you want a relaxing place to stay. Nature enthusiasts will enjoy the lakeside in Chestertown. Make sure you have time to check out the coffeehouses and forests during your trip.

What are some of the best vacation home rentals in Chestertown?

Elizabeth. 15 minutes to Lake George. Seasonal Heated Pool.: This highly rated vacation home rental in Chestertown is located on the waterfront and has an outdoor pool, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games. Our travelers also rate Eagles Nest at Loon Lake near Gore Mountain as a favorite home for rent in Chestertown.

How many vacation rentals will I find in Chestertown?

With 62 Expedia vacation rentals, you're sure to find just the right place for your Chestertown stay.

What’s there to see and do in Chestertown?

Loon Lake Beach and Friends Lake are a couple of lovely local spots to get outside and enjoy nature. Loon Lake and Hudson River are other places to visit while you're in town.

What’s a vacation rental in Chestertown like?

Vacation rentals are private properties you can book for a couple of days or more in Chestertown. Vacation rentals provide amenities like kitchens and laundry facilities so you'll have everything you want. If you're concerned about a clean environment, a vacation rental can provide a sense of security away from shared hotel elevators and busy lobbies while still allowing you a great travel experience. You'll also have more space in a vacation rental than in a standard hotel, which makes a vacation rental a popular option for a small group gathering.

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Check prices for these dates

Our top choices for Chestertown vacation rentals

1. The Lily Pad at Loon Lake near Gore Mountain

2. Authentic Log Cabin with Lake Views and Sauna

3. 2BR+Loft Cabin—Summer Getaway with Patio,Firepit Near Lake George &Gore Mountain

4. Penthouse w/ Best Mtn Views Walk to Gore, Main St | Fast WiFi | Sleeps 6

5. Gore Mountain Lift View: North Creek Main St Apt 2

6. Secluded Adirondack Chalet/7 mins to Gore Mountain/ Fire pit/Fast Wi-Fi.

7. Gore Mountain Views | Luxury Escape for 2–4 • Pets

8. Trout House Village Resort

9. Luxury Retreat | Near Gore Mountain | Pets

10. Walk to Schroon Lake! Studio w/ Shared Fire Pit

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

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

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

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

15. The Office at North Creek All Season Rental

16. Camp RiverWood on the Hudson River

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

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

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

20. Schroon Lake Room < 1 Mi to Marina & Beach!

Find vacation rentals that suit your style

Top Chestertown Hotel Reviews

Fort William Henry Hotel and Conference Center

Nordick's Inn

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

Frequently asked questions

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