Chestertown Holiday Rentals: Short-Term Accommodations for Rent

Q: Can I find holiday rentals in Chestertown?

Yes, there are holiday rentals close to the most popular sights in Chestertown, or you can select a more secluded option if you're looking for a relaxing stay. Nature enthusiasts will enjoy the lakeside in Chestertown. Make sure you have time to check out the coffee shops and forests during your trip.

Q: What are some of the best holiday rentals that Chestertown has to offer?

Elizabeth. 15 minutes to Lake George.Seasonal Heated Pool. : This highly rated holiday home rental in Chestertown is located on the waterfront, and has an outdoor pool, a balcony and a BBQ 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 that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games. Our travellers also rate Eagles Nest at Loon Lake near Gore Mountain as a favourite home for rent in Chestertown.

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

With 62 Expedia holiday rentals, you're guaranteed 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 holiday rental in Chestertown like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Chestertown. Holiday rentals provide amenities like kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about a sanitised environment, a holiday rental can offer a sense of security away from shared hotel lifts and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental an attractive choice for family trips or small group gatherings.

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Chestertown holiday 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.

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.

HK$2,690 total

includes taxes & fees

27 Oct - 28 Oct

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

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

North Creek

Michael

HK$1,693 total

includes taxes & fees

27 Oct - 28 Oct

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

4. Trout House Village Resort

Hague

Matthew

HK$1,104 total

includes taxes & fees

27 Oct - 28 Oct

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.

HK$1,841 total

includes taxes & fees

27 Oct - 28 Oct

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

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

Warrensburg

Matthew L.

HK$1,445 total

includes taxes & fees

27 Oct - 28 Oct

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

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

North Creek

Tara F.

HK$1,928 total

includes taxes & fees

27 Oct - 28 Oct

A room with a bed, a nightstand, and a window.

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

Schroon Lake

Kenneth

HK$1,374 total

includes taxes & fees

27 Oct - 28 Oct

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

9. The Office at North Creek All Season Rental

North Creek

Brandon A.

HK$1,997 total

includes taxes & fees

27 Oct - 28 Oct

A small, single-story building with a porch, a door leading to a bedroom, and a small table with chairs.

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

Schroon Lake

Adam

HK$1,331 total

includes taxes & fees

27 Oct - 28 Oct

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

North Creek

joseph

HK$1,928 total

includes taxes & fees

27 Oct - 28 Oct

A covered porch with a white railing, a white plastic chair, and a view of a park with a swing set and trees.

12. Boat, Fish & Hike! All-Season Schroon Lake Getaway

Schroon Lake

Keith S.

HK$1,374 total

includes taxes & fees

27 Oct - 28 Oct

A grassy outdoor area with a hammock, picnic table, and barbecue grill.

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

Schroon Lake

HK$1,374 total

includes taxes & fees

27 Oct - 28 Oct

A covered porch with two white plastic chairs, a door leading to a room with a bed, and a small window.

14. Cozy Room Near Schroon Lake Marina, Town & Beach!

Schroon Lake

"Julie and her husband went out of their way to make the stay personable and accommodating as possible. Room was clean with everything you would need for the stay. I am already making plans to return to the area and staying right here. Close to town(13 minute walk), great places to dine or check out the beach area. I can’t even think of one negative for a balanced review. This was affordable and very well located."

Susan C.

HK$1,374 total

includes taxes & fees

27 Oct - 28 Oct

A river with large rocks in the foreground and a forested hillside in the background.

15. GLAMP RICHARD ON ADIRONDACK FLOWER FARM

North River

Timothy

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

16. 2BR+Loft Cabin—Summer Getaway with Patio,Firepit Near Lake George &Gore Mountain

Warrensburg

Teresa B.

HK$4,769 total

includes taxes & fees

2 Nov - 3 Nov

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

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

North Creek

Renee B.

HK$2,638 total

includes taxes & fees

27 Oct - 28 Oct

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

18. Luxury Retreat | Near Gore Mountain | Pets

North Creek

HK$4,072 total

includes taxes & fees

29 Oct - 30 Oct

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

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

Warrensburg

Sharon W.

HK$1,671 total

includes taxes & fees

27 Oct - 28 Oct

A covered porch with a table and chairs, a white railing, and a view of a street with a car and greenery.

20. Close to Marina, Beach & Town! Schroon Lake Escape

Schroon Lake

HK$1,331 total

includes taxes & fees

27 Oct - 28 Oct

View all properties

Find holiday 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

La Quinta Inn & Suites by Wyndham Lake George

10/10 Excellent

"Hot tub was not working"

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

Search for holiday rentals in Chestertown on Expedia! You can easily find your home rentals, villas, holiday apartments in Chestertown using one of the methods below:

View our selection of featured holiday rentals in Chestertown
Use the map to find apartments and other holiday homes in the Chestertown neighbourhood you prefer
Enter your travel dates to view the best deals on holiday rentals in Chestertown while they last

Look no further and take a look at our great range of rental properties in Chestertown!

Frequently asked questions

Can I find holiday rentals in Chestertown?

Yes, there are holiday rentals close to the most popular sights in Chestertown, or you can select a more secluded option if you're looking for a relaxing stay. Nature enthusiasts will enjoy the lakeside in Chestertown. Make sure you have time to check out the coffee shops and forests during your trip.

What are some of the best holiday rentals that Chestertown has to offer?

Elizabeth. 15 minutes to Lake George. Seasonal Heated Pool.: This highly rated holiday home rental in Chestertown is located on the waterfront, and has an outdoor pool, a balcony and a BBQ 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 that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games. Our travellers also rate Eagles Nest at Loon Lake near Gore Mountain as a favourite home for rent in Chestertown.

How many holiday rentals will I find in Chestertown?

With 62 Expedia holiday rentals, you're guaranteed 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 holiday rental in Chestertown like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Chestertown. Holiday rentals provide amenities like kitchens and laundry facilities so you'll have all the conveniences of home. If you're concerned about a sanitised environment, a holiday rental can offer a sense of security away from shared hotel lifts and bustling concierge desks while still allowing you the excitement and enjoyment of travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental an attractive choice for family trips or small group gatherings.

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Chestertown holiday rentals

1. The Lily Pad at Loon Lake near Gore Mountain

2. Authentic Log Cabin with Lake Views and Sauna

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

4. Trout House Village Resort

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

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

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

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

9. The Office at North Creek All Season Rental

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

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

12. Boat, Fish & Hike! All-Season Schroon Lake Getaway

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

14. Cozy Room Near Schroon Lake Marina, Town & Beach!

15. GLAMP RICHARD ON ADIRONDACK FLOWER FARM

16. 2BR+Loft Cabin—Summer Getaway with Patio,Firepit Near Lake George &Gore Mountain

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

18. Luxury Retreat | Near Gore Mountain | Pets

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

20. Close to Marina, Beach & Town! Schroon Lake Escape

Find holiday rentals that suit your style

Top Chestertown Hotel Reviews

La Quinta Inn & Suites by Wyndham Lake George

Fort William Henry Hotel and Conference Center

Surfside On The Lake

The Queensbury Hotel

Country Inn & Suites by Radisson, Lake George (Queensbury), NY

The Georgian Lakeside Resort

Friends Lake Inn

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

Find out more about Chestertown

Frequently asked questions

Go further with the Expedia app