Chestertown holiday homes

We found 302 holiday rentals — enter your dates for availability
Select from 62 homes, 19 cottages and other holiday rentals in Chestertown to find one that's perfect for your trip. Whether you're staying in a holiday rental with family or friends, you'll have the best amenities for spending time at your home away from home, which might include parking and a garden. You'll be sure to find a property to rent to meet everyone's needs, including options that are accessible or non-smoking.

Holiday rentals with weekly discounts – Chestertown

Showing deals for:18 Dec - 25 Dec

Living area
Exterior detail
Room
Children’s area
Wonderful
(91 reviews)

SKI TIME! Adirondack Waterfront Log Cabin

Warrensburg

8% off
NZ$8,875
for 7 nights, 1 cabin
NZ$1,268 per night
includes taxes & fees
SKI TIME! Adirondack Waterfront Log Cabin
Dramatic front windows on a sunny day
Private kitchen
Have a seat at the bar and cheer on your chef
Wooden table for 6-8 with comfortable chairs
Exceptional
(90 reviews)

Loon Lake, Chestertown - close to Gore: cozy, clean and bright chalet for 6-8

Chestertown

8% off
NZ$5,056
for 7 nights, 1 chalet
NZ$722 per night
includes taxes & fees
Loon Lake, Chestertown - close to Gore: cozy, clean and bright chalet for 6-8
Living area
Dining
Living area
Private kitchen
Very good
(47 reviews)

Adirondack Rustic 2 Story- 10 ACRES-SKI, SKI, SKI!

Warrensburg

7% off
NZ$6,052
for 7 nights, 1 cabin
NZ$865 per night
includes taxes & fees
Adirondack Rustic 2 Story- 10 ACRES-SKI, SKI, SKI!
Dinning room
Property grounds
Back of lodge.
Great room with fireplace.
Exceptional
(44 reviews)

Beautiful Adirondack Lodge just 15 Minutes from Gore Mt ski area & Lake George

Warrensburg

8% off
NZ$11,436
for 7 nights, 1 room
NZ$1,634 per night
includes taxes & fees
Beautiful Adirondack Lodge just 15 Minutes from Gore Mt ski area & Lake George
Family room
Lake View House
Interior
Dining room
Exceptional
(150 reviews)

Hickory Hill Mountaintop charming family friendly quiet very private lake view

Bolton Landing

8% off
NZ$11,943
for 7 nights, 1 home
NZ$1,706 per night
includes taxes & fees
Hickory Hill Mountaintop charming family friendly quiet very private lake view
Marina
Outdoor dining
Interior
Exterior
Exceptional
(30 reviews)

Lake side Chalet Brant Lake w/ outdoor Hot Tub

Brant Lake

8% off
NZ$6,795
for 7 nights, 1 home
NZ$971 per night
includes taxes & fees
Lake side Chalet Brant Lake w/ outdoor Hot Tub
Exterior detail
Outdoor dining
Exterior
Dining
Exceptional
(44 reviews)

The perfect ADK log cabin getaway on 4 acres and 5 min. to town!

Schroon Lake

7% off
NZ$6,067
for 7 nights, 1 cabin
NZ$867 per night
includes taxes & fees
The perfect ADK log cabin getaway on 4 acres and 5 min. to town!
Dining
Interior
Living area
Living area
Exceptional
(43 reviews)

Modern Cabin w/ Hot Tub-Minutes to Lakes & Skiing

Chestertown

9% off
NZ$5,457
for 7 nights, 1 room
NZ$780 per night
includes taxes & fees
Modern Cabin w/ Hot Tub-Minutes to Lakes & Skiing
Open concept living space
Gas grill with a water view
Living room view to lake
Screened balcony off of Master Bedroom
Exceptional
(10 reviews)

Lakefront townhome on Tripp Lake in the Adirondacks, minutes from Gore Mountain skiing, Lake George, hiking, kayaking, and year-round outdoor adventure.

Chestertown

12% off
NZ$3,789
for 7 nights, 1 home
NZ$541 per night
includes taxes & fees
Lakefront townhome on Tripp Lake in the Adirondacks, minutes from Gore Mountain skiing, Lake George, hiking, kayaking, and year-round outdoor adventure.
Exterior
Outdoor spa tub
Living room with queen sofa bed memory foam mattress
Living room with 4 sitting bar
Exceptional
(19 reviews)

Adirondack home, near Gore Mt ski resort, North Creek, and Loon lake.

Chestertown

8% off
NZ$5,699
for 7 nights, 1 home
NZ$814 per night
includes taxes & fees
Adirondack home, near Gore Mt ski resort, North Creek, and Loon lake.
Front Entry
Rear patio fire pit
Exterior
Private kitchen
Exceptional
(27 reviews)

The Bolton House - 5 BR 3.5 BA Home with Hot Tub

Bolton Landing

8% off
NZ$19,791
for 7 nights, 1 home
NZ$2,827 per night
includes taxes & fees
The Bolton House - 5 BR 3.5 BA Home with Hot Tub
Front door.
Private oasis.
Gather the friends and family around the table for good food and games.
Entry.
Exceptional
(16 reviews)

Vintage ADK Cabin- Great Deal, Perfect Location, book your Gore Mtn. trip today!

Pottersville

12% off
NZ$2,608
for 7 nights, 1 cabin
NZ$373 per night
includes taxes & fees
Vintage ADK Cabin- Great Deal, Perfect Location, book your Gore Mtn. trip today!
Vaulted Ceiling kitchen, Fresh, Clean, Renovated
Post Beam Barn and a fire pit.
Stairwell with hemlock wide plank floors.
GORE Close by -11 minute drive
Exceptional
(59 reviews)

Near The Black Hole, swim, SKI GORE nearby, Walking trail,Trout stream, Hiking,

Wevertown

8% off
NZ$4,538
for 7 nights, 1 home
NZ$648 per night
includes taxes & fees
Near The Black Hole, swim, SKI GORE nearby, Walking trail,Trout stream, Hiking,
King beds in all of the high ceilinged bedrooms.
Life is about who you spend your time with. In the great room - only smiles!
Relax in the great room, in classic Adirondack style!
Fireplace and kitchen open up to the dining area and great room.
Exceptional
(6 reviews)

Our property has sold! Contact us to direct you to the new owner's VRBO listing!

Chestertown

8% off
NZ$3,760
for 7 nights, 1 apartment
NZ$537 per night
includes taxes & fees
Our property has sold! Contact us to direct you to the new owner's VRBO listing!
Lodge entryway, looking towards living room.
2018 New sitting area around fire pit
Living room from loft
Living room
Exceptional
(57 reviews)

Lakefront spacious contemporary. Large families welcome. Ski GORE nearby!

Chestertown

8% off
NZ$5,990
for 7 nights, 1 home
NZ$856 per night
includes taxes & fees
Lakefront spacious contemporary. Large families welcome. Ski GORE nearby!
Private kitchen
Interior
Property grounds
Interior
Exceptional
(50 reviews)

Rustic Adirondack Retreat on Tripp Lake

Chestertown

7% off
NZ$2,994
for 7 nights, 1 home
NZ$428 per night
includes taxes & fees
Rustic Adirondack Retreat on Tripp Lake

  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support

  • More quality time

    From booking to staying, the whole process is simple and enjoyable

  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more

  • More for less

    More space, more privacy, more amenities — more value

Head to the secluded city of Chestertown

The lake and forests provide a pleasant backdrop to your holiday home in Chestertown. Travellers to this relaxing city praise the coffee shops, canoeing and horse riding. If you need more space to accommodate a family holiday or a trip with friends, rental homes often come with separate dining areas and spacious living rooms.

Sightseeing in and around Chestertown

Are you hoping to find top things to see and do during your stay? Although it can be tempting to stay in your comfortable holiday rental, you'll want to check out everything that makes Chestertown a fun spot to go on holiday. Here are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • The Sagamore Golf Club (8.2 mi / 13.2 km)
  • Gore Mountain Ski Resort (10.4 mi / 16.7 km)
  • Garnet Hill Lodge and Ski Resort (15.8 mi / 25.5 km)
  • Adirondack Winery (16.3 mi / 26.2 km)
  • Tubby Tubes Company (19.6 mi / 31.6 km)
  • Great Escape (21.6 mi / 34.7 km)

Exploring the natural features in Chestertown

Whether you're an outdoor enthusiast or just want to spend some time taking in the scenery, Chestertown is a great place to get outside. These are a few of the area's most eye-catching sights, all within 30 miles (48.2 km) of the city centre:

  • Loon Lake Beach (2 mi / 3.3 km)
  • Friends Lake (2.8 mi / 4.5 km)
  • Loon Lake (3.2 mi / 5.2 km)
  • Natural Stone Bridge and Caves (7 mi / 11.3 km)
  • Schroon Lake (9.6 mi / 15.4 km)
  • Lake George (12.3 mi / 19.9 km)

Travelling to and around Chestertown

Fly into Glens Falls, NY (GFL-Floyd Bennett Memorial), the closest airport, located 23.6 mi (38 km) from the city centre.

Frequently asked questions

What is the best area to stay in Chestertown when booking a holiday rental?
When considering a holiday rental in Chestertown, New York, the charming area surrounding the town centre is an excellent choice. This locality offers a delightful blend of scenic beauty and local character, making it ideal for those looking to immerse themselves in the tranquility of the Adirondacks.Chestertown is known for its proximity to the stunning Schroon Lake, a popular spot for swimming, kayaking, and fishing during the warmer months. Additionally, the nearby Gore Mountain provides thrilling opportunities for skiing and snowboarding in the winter, drawing outdoor enthusiasts year-round.The town centre itself features a selection of quaint shops, eateries, and local cafes, allowing visitors to experience the warm hospitality of the region. With a variety of properties available, from cosy cabins to charming cottages, guests can find accommodations that suit their needs and preferences.
Where are the best areas for renting a beach house in Chestertown?
For renting a beach house in Chestertown, the area around Lake George is particularly appealing, as it offers a range of properties with scenic waterfront views. The hamlet of Pottersville, located just a short drive from Chestertown, features charming cottages and cabins that often come with private docks, outdoor seating areas, and fire pits, great for enjoying summer evenings by the water.Nearby, the Lake George Village area provides additional options for holiday rentals, including larger family homes with spacious backyards and amenities such as barbecue grills and game rooms. Many properties here offer easy access to the lake for swimming and boating, with some featuring kayaks or paddleboards for guest use.In addition, Chestertown itself is surrounded by the stunning natural beauty of the Adirondacks, making it a great base for outdoor activities. Rentals in the area often include access to hiking trails, with some properties located near popular spots for fishing and wildlife watching.
Where are the best Chestertown ski resort rentals?
For the best ski resort rentals near Chestertown, New York, consider the nearby area of Gore Mountain. Located approximately 20 minutes away, this popular ski destination offers a variety of rental options. In Chestertown itself, visitors can find charming cabins and lodges that provide a cozy retreat after a day on the slopes. Many of these properties feature amenities such as fully equipped kitchens, fireplaces, and outdoor decks with scenic views of the surrounding Adirondack Mountains.In the vicinity of Gore Mountain, you'll also discover an array of holiday rentals, including ski-in/ski-out lodgings and spacious chalets that cater to larger groups or families. These accommodations often come with modern conveniences like Wi-Fi, hot tubs, and game rooms, providing a superb balance of comfort and entertainment.Chestertown is located among beautiful natural landscapes, offering not just skiing but also opportunities for hiking and exploring the picturesque surroundings. The local community provides access to quaint shops and dining, allowing guests to enjoy the charm of small-town life while being close to outdoor adventures.
What is the most popular type of holiday rental accomodation in Chestertown?
In Chestertown, holiday houses are the most popular type of holiday rental, with about 165 available throughout the area. These houses often feature spacious layouts with multiple bedrooms, fully equipped kitchens, and outdoor spaces for enjoying the picturesque views of the surrounding nature. Many come with amenities such as fireplaces and BBQ grills, making them ideal for families or groups looking for a comfortable retreat.Additionally, there are approximately 51 charming cottages that provide a quaint, homely atmosphere, great for those seeking a more rustic experience. Cabins, numbering around 36, offer a unique stay in the heart of the Adirondack Mountains, often equipped with cozy interiors and access to beautiful hiking trails.
Are there any family house rentals in Chestertown?
In Chestertown, New York, there are numerous family-friendly house rentals available, with around 84 options to choose from. This charming area is located in the beautiful Adirondack Mountains, providing a superb backdrop for outdoor adventures. Many of these homes feature spacious living areas, fully equipped kitchens for preparing meals together, and outdoor decks where families can enjoy the fresh mountain air.Visitors can explore nearby attractions such as the stunning Lake George and the picturesque hiking trails of the surrounding forests. Properties often include amenities like Wi-Fi, laundry facilities, and sometimes even game rooms or fire pits for evening gatherings.
Can I rent a holiday home with a pool or hot tub in Chestertown?
In Chestertown, there are several holiday homes available for rent that feature pools and hot tubs, with around 12 options to choose from. This picturesque town, located in the Adirondack Mountains, offers a serene getaway for those looking to relax and enjoy nature. Many of these properties come equipped with private pools and hot tubs, making them ideal for families or groups seeking a tranquil retreat. Additionally, amenities such as spacious outdoor decks, fully equipped kitchens, and cosy living areas are commonly found, ensuring a comfortable stay.
Are there pet-friendly house rentals in Chestertown?
In Chestertown, there are numerous pet-friendly house rentals available, offering a range of options for travellers with furry companions. Many of these properties feature amenities such as spacious gardens, outdoor decks, and fully equipped kitchens, making them suitable for both relaxation and convenience during your stay.The area is surrounded by the natural beauty of the Adirondack Mountains, providing ample opportunities for outdoor activities like hiking and exploring. Nearby, the picturesque Loon Lake offers opportunities for swimming and kayaking, where pets are often welcome. Furthermore, the Chestertown area boasts local parks and trails that are great for walking your dog, ensuring that both you and your pet can enjoy the scenic surroundings.
Are there any remote work holiday rentals in Chestertown?
In Chestertown, New York, there are a substantial number of remote work holiday rentals available, with around 264 options to choose from. This picturesque town, located in the Adirondack Mountains, offers a tranquil setting for those looking to combine work and leisure. Many of the properties are equipped with essential amenities for remote work, including high-speed Wi-Fi and dedicated workspaces, ensuring a productive environment.Travellers can expect a variety of accommodations, ranging from cosy cabins to spacious homes, often featuring comfortable living areas, full kitchens for meal preparation, and outdoor spaces to enjoy the natural surroundings. The area is known for its stunning landscapes, with opportunities for hiking, fishing, and enjoying the local wildlife, making it an ideal location for a work-cation. To help narrow your search, insert your dates and apply the "WiFi" filter on Bookabach.
What are popular rental amenities in Chestertown?
In Chestertown, popular rental amenities include fully equipped kitchens, allowing guests to prepare their own meals. Many properties also offer onsite parking for convenience. Outdoor spaces, such as decks or patios, provide a lovely setting for relaxation amidst the picturesque surroundings. Additionally, you can expect amenities like coffee and tea makers for those early morning brews, and fireplaces that create a warm, inviting atmosphere during cooler evenings.
When is the best time to visit Chestertown for a holiday rental?
The best time to visit Chestertown for a holiday rental is during the peak season from June to August, with July being the most popular month among travellers. This vibrant period attracts outdoor enthusiasts eager to take advantage of the warm weather, with plenty of opportunities for hiking, kayaking, and exploring the stunning natural beauty of the Adirondacks.During these summer months, visitors can expect pleasant temperatures averaging between 15 to 25 degrees Celsius, great for enjoying the local lakes and picturesque scenery. The town also comes alive with community events and the chance to connect with both locals and fellow travellers, creating a lively option that enhances your holiday experience.For those looking to save a bit, November offers a quieter alternative. While it may be less bustling, this month presents a unique charm with the tranquility of early winter setting in, allowing for peaceful walks amidst the crisp air and the chance to enjoy the serene landscapes without the crowds.Whether you're drawn to the excitement of summer activities or the calm of the shoulder season, Chestertown has something special to offer throughout the year.
What are the top attractions in Chestertown?
In Chestertown, visitors can enjoy a variety of attractions that highlight the area's natural beauty and outdoor activities. The stunning Schroon Lake is a major draw, offering opportunities for swimming, fishing, and boating, with several waterfront parks for picnicking and relaxation. The nearby Hudson River is superb for canoeing and kayaking, making it a great spot for water enthusiasts.The charming town itself features quaint shops and local eateries, providing a taste of the community's hospitality. For those interested in hiking, the surrounding Adirondack Mountains offer numerous trails with breathtaking views, including the nearby Pharaoh Mountain Wilderness Area, which is popular for its scenic vistas and diverse wildlife.
Are all fees included in the Chestertown holiday homes prices shown on Bookabach?
Bookabach provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Chestertown holiday homes with parking?
Bookabach offers a wide selection of holiday homes in Chestertown with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Chestertown holiday homes?
You can find great discounts on holiday homes in Chestertown on Bookabach, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Chestertown holiday home booking on Bookabach?
To find Chestertown holiday rentals with free cancellation, just use Bookabach's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Bookabach makes it easy to book with confidence.
Can I find long-stay holiday homes in Chestertown?
A long-stay holiday home in Chestertown is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Bookabach?
Bookabach's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Chestertown holiday home?
Book your Chestertown holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Bookabach booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Chestertown?
Prices for holiday homes in Chestertown vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Bookabach offers something for every taste and budget, from affordable homes in Chestertown to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Bookabach as a host?
Joining Bookabach as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Bookabach makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.