Photo by Julie Miller

Find Extended Stay Hotels in Chestertown, NY

Start date: Check-in selected.
To Date
End date: Check-out

Top Chestertown Extended Stay Hotels | Reserve now, pay later

Our top choices for Chestertown hotels with a kitchen

Smart TV, books
Cozy 3BR 3.5BA Lodge w/ Lake & Beach Access, Screened in Patio, Grill, Sunroom

Cozy 3BR 3.5BA Lodge w/ Lake & Beach Access, Screened in Patio, Grill, Sunroom

Cozy 3BR 3.5BA Lodge w/ Lake & Beach Access, Screened in Patio, Grill, Sunroom
Chestertown
10.0 out of 10, Exceptional, (3)
"Rooms were very clean. Location was great, next to many hiking spots. However, far from many common stores. Was beautiful "
United States
MiaMaria C.
$425 nightly
The price is $472
Dec 13 - Dec 14
Total with taxes and fees
Cozy 3BR 3.5BA Lodge w/ Lake & Beach Access, Screened in Patio, Grill, Sunroom
Outdoor dining
The Lily Pad at Loon Lake near Gore Mountain

The Lily Pad at Loon Lake near Gore Mountain

The Lily Pad at Loon Lake near Gore Mountain
Chestertown
9.6 out of 10, Exceptional, (39)
"Comfortable stay with extended family. Would definitely stay again."
United States
Pam V.
$400 nightly
The price is $444
Dec 14 - Dec 15
Total with taxes and fees
The Lily Pad at Loon Lake near Gore Mountain
Smart TV
Authentic Log Cabin with Lake Views and Sauna

Authentic Log Cabin with Lake Views and Sauna

Authentic Log Cabin with Lake Views and Sauna
Chestertown
$423 nightly
The price is $470
Dec 14 - Dec 15
Total with taxes and fees
Authentic Log Cabin with Lake Views and Sauna
Basic Cabin | Private kitchen | Fridge, microwave, coffee/tea maker, electric kettle
Maple Leaf Motel

Maple Leaf Motel

Maple Leaf Motel
2.5 star property
Schroon Lake
8.8 out of 10, Excellent, (548)
"Convenient check in, good value."
United States
Dalei
$119 nightly
The price is $134
Dec 13 - Dec 14
Total with taxes and fees
Maple Leaf Motel
Free daily continental breakfast
Best Western of Lake George

Best Western of Lake George

Best Western of Lake George
2.5 star property
Lake George
7.8 out of 10, Good, (1000)
"Nice place "
United States
Frederick
$71 nightly
The price is $78
Dec 14 - Dec 15
Total with taxes and fees
Best Western of Lake George
Restaurant
Home2 Suites by Hilton Queensbury Lake George

Home2 Suites by Hilton Queensbury Lake George

Home2 Suites by Hilton Queensbury Lake George
3.0 star property
Queensbury
9.2 out of 10, Wonderful, (824)
"Room for as ready early after long trip and staff person was very nice when we got here !"
United States
Frederick
$85 nightly
The price is $94
Jan 4 - Jan 5, 2026
Total with taxes and fees
Home2 Suites by Hilton Queensbury Lake George
Cabin, 1 Bedroom, Non Smoking, Lake View | Egyptian cotton sheets, premium bedding, individually decorated
Trout House Village Resort

Trout House Village Resort

Trout House Village Resort
3.0 star property
Hague
9.8 out of 10, Exceptional, (18)
"Very friendly owner and beautiful views"
United States
Anthony
$189 nightly
The price is $210
Dec 13 - Dec 14
Total with taxes and fees
Trout House Village Resort
Premium Chalet, Multiple Beds | Exterior
Lodge at Schroon Lake

Lodge at Schroon Lake

Lodge at Schroon Lake
3.0 star property
Schroon Lake
9.0 out of 10, Wonderful, (414)
"Nice restaurant- welcoming staff, good live music! "
United States
Kathleen
$160 nightly
The price is $180
Dec 21 - Dec 22
Total with taxes and fees
Lodge at Schroon Lake
Sunrise Kitchen, Studio | View from room
Motel Luzerne

Motel Luzerne

Motel Luzerne
2.0 star property
Lake Luzerne
8.8 out of 10, Excellent, (171)
"What a great little Inn. My room was clean with a comfy bed. I must come back in the season with my wife as i found very relaxing with a great lake view"
United States
Gabriel
$76 nightly
The price is $84
Dec 14 - Dec 15
Total with taxes and fees
Motel Luzerne
Exterior
Llama House ADK

Llama House ADK

Llama House ADK
2.5 star property
Wevertown
9.2 out of 10, Wonderful, (31)
"This is a great place to stay. The room was very cooly decorated and the bed was incredibly comfortable with high quality linens. The location is spectacular with great walks and a swimming hole nearby."
United States
Lissa
$137 nightly
The price is $153
Dec 16 - Dec 17
Total with taxes and fees
Llama House ADK
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
View all properties

Expand your search

Most booked related extended stays in Chestertown in 2026

Chestertown apart-hotels
Apart-hotels for extended stays
Apart-hotels for extended stays
Chestertown vacation homes with a kitchen
Vacation homes with a kitchen
Vacation homes with a kitchen

Frequently asked questions

What are the best long-term hotels in Chestertown?
With an oven, a patio and other amenities, Lakefront Home Steps Away From Sandy Beach And Fire Pit is perfect for your extended stay in Chestertown. Another excellent choice is 3 Chester @ Birchwood Cottages At Loon Lake. Family Friendly Waterfront. Check in here and enjoy access to an oven, a porch and more. Both long-term hotels also offer a kitchenette or full kitchen where you can whip up your favorite home-cooked meals. Use the money you save on takeouts for awesome things like tours and activities.
What are the top pet-friendly extended stay hotels in Chestertown?
Your best friend doesn't have to feel left out when you go on vacation. Spend your extended stay in Chestertown at Fireside Cabin, Wonderful Cozy Adirondack Cabin Steps From Loon Lake. This pet-friendly escape offers amenities such as pet-friendly services and a garden. 3 Chester @ Birchwood Cottages At Loon Lake. Family Friendly Waterfront will also roll out the welcome mat for your loveable pooch. It features pet-friendly services, a porch and more.
Are there any extended stay apartments in Chestertown?
More than just a place to sleep and shower, an apartment has the ability to make you feel at home. For your extended stay in Chestertown, check out Lily Pad South At Loon Lake Near Gore Mountain. It features a kitchen, an oven and a queen bed and is just a quick drive from downtown. Alternatively, unpack your suitcase at Lily Pad North At Loon Lake Near Gore Mountain. It's also an easy commute from central Chestertown and offers a dryer and a queen bed. Want to make homemade meals for yourself? There's a kitchen for you to make use of too.
What's the best extended stay hotel in downtown Chestertown?
Take in the sights and sounds of Chestertown from Lakefront Home Steps Away From Sandy Beach And Fire Pit. Featuring conveniences such as a queen bed and a nearby laundromat, you'll be rubbing shoulders with the locals while staying in the center of this fantastic destination. Want more options? Try Tripp Lake Retreat, A Great Place To Make Adirondack Memories. Another extended stay hotel that puts you in the downtown area, it offers a deck and a patio. When you're ready to sample some of the most popular attractions in town, Friends Lake and Loon Lake Beach should be on your travel itinerary.
What are the best extended stay hotels with kitchens in Chestertown?
When you're on the road for a long time with your family, eating out all the time can be stressful — not to mention pricey. That's why it's smart to opt for long-term stays equipped with a kitchen, like Lakefront Home With Wifi, Dock. It offers a range of features that make vacationing with your crew more enjoyable, including a water park and a nearby beach. Great Family Getaway Location will also help you save a small fortune on restaurants. Whip up your favorite meals and use this property's amenities, such as a barbecue grill and free WiFi.
Can I find extended stay hotels with pools in Chestertown?
Roll out of bed, cook breakfast and then spend the day in the pool. If that sounds like your ideal vacation, you'll love Sleepy Hollow, Wonderful Adirondack Mountains Cabin Steps From Loon Lake. It comes with all the useful amenities you need for an extended stay in Chestertown, from kitchen facilities and a pool to a swimming pool and cable/satellite TV services. Fireside Cabin, Wonderful Cozy Adirondack Cabin Steps From Loon Lake also promises lots of poolside rest and relaxation. A swimming pool and a queen bed are two of the reasons this stay is a favorite with guests.Chestertown has a humid continental climate and temperatures range between 53 ºF and 77 ºF in the summer months. If you're hoping to spend a large portion of your getaway splashing around in the water, this is an ideal time to visit.
What are the top extended stay hotels with 2 bedrooms in Chestertown?
Hit the road with your friends or family and then set up camp at Fireside Cabin, Wonderful Cozy Adirondack Cabin Steps From Loon Lake. Two bedrooms, a swimming pool and a barbecue grill help make this property ideal for long-term stays in Chestertown. Or, check in at Great Family Getaway Location. It has a dryer, a queen bed and two bedrooms, which means you'll have plenty of space to take it easy after sightseeing activities.
Why book an extended stay hotel in Chestertown through Expedia?
Book your extended stay hotel in Chestertown with Expedia and get the best price without having to check dozens of websites. In addition to our unbeatable offers and reward programs, we make finding the perfect long-term stay a snap. Use our handy filter to search for accommodations based on location, nearby attractions, ratings and more. Some long-term rentals may offer weekly rates to help you keep extra cash in your pocket. Often equipped with the comforts of home like a kitchen and dining area, your next extended stay in Chestertown is just a couple of clicks away!
What can I expect from an extended stay hotel?
Featuring amenities such as kitchens, dining areas and laundries, extended stay hotels in Chestertown can be a comfortable and budget-friendly alternative to your standard hotel room. Make home-cooked meals and save on laundromat bills. Sometimes offering discounted weekly rates, extended stay hotels range from cozy studios to options with several bedrooms. They also offer many of the same amenities you'd expect to find in a standard hotel, like pools or 24/7 guest services. If you're after flexibility, privacy and a relaxing retreat for a few weeks or more, an extended stay hotel is the perfect choice.

Top Chestertown Hotel Reviews

Lodges At Cresthaven

Lodges At Cresthaven

10/10 Excellent
"Great !"
Alexandra 4-night trip
Posted 3 weeks ago
Lodges At Cresthaven

Explore a world of travel with Expedia