Chestertown Holiday Rentals from €151: Search Short-Term Rentals

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.

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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.

includes taxes & fees

9 Nov - 10 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.

includes taxes & fees

9 Nov - 10 Nov

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

includes taxes & fees

9 Nov - 10 Nov

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

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

Warrensburg

Matthew L.

includes taxes & fees

29 Nov - 30 Nov

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

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

Schroon Lake

Kenneth

includes taxes & fees

9 Nov - 10 Nov

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

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

North Creek

Lynda N.

includes taxes & fees

9 Nov - 10 Nov

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

7. 2BR+Loft Cabin—Summer Getaway with Patio,Firepit Near Lake George &Gore Mountain

Warrensburg

Teresa B.

includes taxes & fees

9 Nov - 10 Nov

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

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

Schroon Lake

Keith S.

includes taxes & fees

9 Nov - 10 Nov

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

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

Schroon Lake

Adam

includes taxes & fees

9 Nov - 10 Nov

A street view with parked cars, a building with a sign that reads 'Lodge Department Store,' and a pink building with a sign that reads 'White Beautiful.'

10. 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.

includes taxes & fees

9 Nov - 10 Nov

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

North Creek

includes taxes & fees

9 Nov - 10 Nov

View all properties

Find holiday rentals that suit your style

Find out more about Chestertown

Everything you need to know about Chestertown holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Chestertown holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Chestertown holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Chestertown holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Chestertown. If you’re looking for a little peace, consider booking during the quieter months, such as . For more hustle and bustle, you may prefer to visit in .

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Chestertown holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Chestertown holiday rentals we have selected for you start as low as €151 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Chestertown rentals

At Expedia, we put the best Chestertown holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia.

To find some top Chestertown rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Chestertown holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Chestertown. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence.

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.

Holiday Rentals in Chestertown

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. Gore MTN & Saratoga ADK Crash Pad! The Cocoon

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

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

7. 2BR+Loft Cabin—Summer Getaway with Patio,Firepit Near Lake George &Gore Mountain

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

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

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

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

12. Trout House Village Resort

13. The Office at North Creek All Season Rental

14. Luxury Retreat | Near Gore Mountain | Pets

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

16. 7 minutes to Gore Mountain skiing, 4 bdrm, sleeps 10

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

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

19. ADK Rustic Private Chalet Viewing Two Ponds / Forest 5.3 miles To Gore Mountain

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

Find holiday rentals that suit your style

Find out more about Chestertown

Chestertown holiday rentals: An excellent choice for every season

How to find incredible deals on Chestertown rentals

Frequently Asked Questions

Can I find holiday rentals in Chestertown?

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

How many holiday rentals will I find in Chestertown?

What’s there to see and do in Chestertown?

What’s a holiday rental in Chestertown like?