Chestertown Vacation Rentals from SAR 717: 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.

Check prices for these dates

In two weeks

In two months

In three months

In four months

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.

SAR 1,583 total

includes taxes & fees

15 Nov - 16 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.

SAR 1,225 total

includes taxes & fees

16 Nov - 17 Nov

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

SAR 1,125 total

includes taxes & fees

28 Nov - 29 Nov

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

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

North Creek

Schroon Lake

A rustic cabin with a triangular roof, surrounded by a forest. There are two red chairs and a fire pit in front.

20. Little Black Aframe by the Brook- 5m to Waterfall

Warrensburg

Sharon W.

SAR 774 total

includes taxes & fees

15 Nov - 16 Nov

View all properties

Find vacation rentals that suit your style

Apartments

Cabins

Save an average of 15% on thousands of hotels when you're signed in

Sign in

Sign up, it's free

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!"

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.

Room 1

Change your mind

Treat yourself

Be picky

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. Gore MTN & Saratoga ADK Crash Pad! The Cocoon

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

5. 2BR+Loft Cabin—Summer Getaway with Patio,Firepit Near Lake George &Gore Mountain

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

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

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

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

10. The Office at North Creek All Season Rental

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

12. Luxury Retreat | Near Gore Mountain | Pets

13. Camp RiverWood on the Hudson River

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

15. Trout House Village Resort

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

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

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

19. Easy Schroon Lake Living! Close to Marina & Town

20. Little Black Aframe by the Brook- 5m to Waterfall

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.

Frequently asked questions

Go further with the Expedia app