Chestertown holiday homes

We found 296 holiday rentals — enter your dates for availability
Select from 60 homes, 20 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:13 Nov - 20 Nov

Living area
Exterior detail
Terrace/patio
Room
Wonderful
(87 reviews)

SKI TIME! Adirondack Waterfront Log Cabin

Warrensburg

8% off
NZ$8,699
for 7 nights, 1 cabin
NZ$1,243 per night
includes taxes & fees
SKI TIME! Adirondack Waterfront Log Cabin
Interior
Dining area
Screened porch
Loft | 2 Full Beds
Exceptional
(12 reviews)

Spacious log cabin in Warrensburg w/ Hot Tub: 15 Mi to Lake George

Warrensburg

6% off
NZ$14,919
for 7 nights, 1 cabin
NZ$2,131 per night
includes taxes & fees
Spacious log cabin in Warrensburg w/ Hot Tub: 15 Mi to Lake George
Solitude
Dining
Private kitchen
Living area
Very good
(46 reviews)

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

Warrensburg

7% off
NZ$5,978
for 7 nights, 1 cabin
NZ$854 per night
includes taxes & fees
Adirondack Rustic 2 Story- 10 ACRES-SKI, SKI, SKI!
Exterior detail
Outdoor dining
Super comfortable futon.
Exterior
Exceptional
(40 reviews)

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

Schroon Lake

7% off
NZ$5,316
for 7 nights, 1 cabin
NZ$759 per night
includes taxes & fees
The perfect ADK log cabin getaway on 4 acres and 5 min. to town!
Dining room
Lake View House
Family room
Interior
Exceptional
(148 reviews)

Hickory Hill Mountaintop charming family friendly quiet very private lake view

Bolton Landing

8% off
NZ$12,103
for 7 nights, 1 home
NZ$1,729 per night
includes taxes & fees
Hickory Hill Mountaintop charming family friendly quiet very private lake view
Interior
Outdoor dining
Room
Marina
Exceptional
(28 reviews)

Lake side Chalet Brant Lake w/ outdoor Hot Tub

Brant Lake

8% off
NZ$6,711
for 7 nights, 1 home
NZ$959 per night
includes taxes & fees
Lake side Chalet Brant Lake w/ outdoor Hot Tub
Living area
Interior
Living area
Dining
Exceptional
(43 reviews)

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

Chestertown

9% off
NZ$3,871
for 7 nights, 1 room
NZ$553 per night
includes taxes & fees
Modern Cabin w/ Hot Tub-Minutes to Lakes & Skiing
Front door.
Private oasis.
Gather the friends and family around the table for good food and games.
Entry.
Exceptional
(14 reviews)

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

Pottersville

12% off
NZ$2,576
for 7 nights, 1 cabin
NZ$368 per night
includes taxes & fees
Vintage ADK Cabin- Great Deal, Perfect Location, book your Gore Mtn. trip today!
Living room view to lake
Gas grill with a water view
Master bedroom - King bed, smart TV, private lake view balcony
Screened balcony off of Master Bedroom
Exceptional
(8 reviews)

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

Chestertown

11% off
NZ$2,711
for 7 nights, 1 home
NZ$387 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.
Living room with queen sofa bed memory foam mattress
Outdoor spa tub
Living room with 4 sitting bar
Exterior
Exceptional
(19 reviews)

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

Chestertown

8% off
NZ$4,169
for 7 nights, 1 home
NZ$596 per night
includes taxes & fees
Adirondack home, near Gore Mt ski resort, North Creek, and Loon lake.
Interior
Outdoor dining
Private kitchen
Room
Exceptional
(10 reviews)

Cozy lil' Cabin in the Adirondacks with fireplace.

North Creek

8% off
NZ$2,581
for 7 nights, 1 home
NZ$369 per night
includes taxes & fees
Cozy lil' Cabin in the Adirondacks with fireplace.
King beds in all of the high ceilinged bedrooms.
Life is about who you spend your time with.  In the great room - only smiles!
Ensuite bathrooms in all bedrooms featuring dual pedestal sinks and large shower
Relax in the great room, in classic Adirondack style!
Exceptional
(6 reviews)

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

Chestertown

8% off
NZ$3,714
for 7 nights, 1 apartment
NZ$531 per night
includes taxes & fees
Our property has sold! Contact us to direct you to the new owner's VRBO listing!
To the Living Room. Leather/2 leather Mission oak Recliners for your comfort
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$4,253
for 7 nights, 1 home
NZ$608 per night
includes taxes & fees
Near The Black Hole, swim, SKI GORE nearby, Walking trail,Trout stream, Hiking,
The Lodge at Birchwood Cottages at Loon Lake 8-2018
2018 New sitting area around fire pit
Lodge entryway, looking towards living room.
Living room from loft
Exceptional
(57 reviews)

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

Chestertown

8% off
NZ$5,917
for 7 nights, 1 home
NZ$845 per night
includes taxes & fees
Lakefront spacious contemporary. Large families welcome. Ski GORE nearby!
Wedding Fall 2023
Deck and View
Dining Room and Kitchen
Cabin
Exceptional
(47 reviews)

Private Cabin with Mt View & hot-tub. Near Gore, Placid & Lake George. Sleeps 15

Johnsburg

8% off
NZ$8,504
for 7 nights, 1 home
NZ$1,215 per night
includes taxes & fees
Private Cabin with Mt View & hot-tub. Near Gore, Placid & Lake George. Sleeps 15
Dining Room
Gas Fireplace
Kitchen
Balcony
Exceptional
(109 reviews)

Secluded and Cozy Townhome at Tripp Lake

Chestertown

12% off
NZ$3,105
for 7 nights, 1 home
NZ$444 per night
includes taxes & fees
Secluded and Cozy Townhome at Tripp Lake
Private kitchen
Interior
Property grounds
Room
Exceptional
(49 reviews)

Rustic Adirondack Retreat on Tripp Lake

Chestertown

7% off
NZ$2,957
for 7 nights, 1 home
NZ$422 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)
  • Six Flags Great Escape (21.6 mi / 34.7 km)
  • Hiland Golf and Country Club (22 mi / 35.4 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:

  • Lake George (12.3 mi / 19.9 km)
  • 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)

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 most popular type of holiday home accommodation in Chestertown?
The most sought-after types of holiday homes in Chestertown are houses. Want something different? Bookabach has many options to match the unique needs of our guests, so you'll see holiday properties in all shapes and sizes, and for all budgets. The perfect fit is waiting for you — lock in yours today.
How much does it cost to rent a holiday home in Chestertown?
The average price for a holiday home in Chestertown can vary depending on factors like time of year, length of stay and property type. Whether you prefer a sprawling villa with space for the whole family or a cosy cabin for just you and the kids, just enter your dates of travel to see stays that offer great value.
How much does it cost to rent a beach house in Chestertown?
When you travel and the style and size of the property will determine the cost of your beachside holiday home. Put in your Chestertown travel dates to see all your options on Bookabach. Can't live without a private pool? Use our filters to select the features and amenities you want.
Are there pet-friendly holiday homes in Chestertown?
You're in luck. There are. Take your pick of 14 stays that welcome pets in Chestertown on Bookabach. Our furry companions also need a break, so simply use our search function for pet-friendly holiday homes to find a pad where Rover can join the fun.
What are popular home amenities in Chestertown?
Tennis, an electric car charging station and nearby museums rank as the most popular home amenities in Chestertown. Whether you're travelling alone, with your significant other or a group of dear friends, Bookabach will help you find a holiday home that matches your tastes with all the features you're looking for.
Are there large group holiday homes in Chestertown?
Chestertown has six holiday properties that can fit 10 or more guests. These stays come with all the space you need to enjoy good times with your favourite people.
Are there holiday homes in Chestertown that welcome kids?
With 14 family-friendly holiday homes available in Chestertown, now is a great time to introduce the kids to the joys of travel. Simply click on our "Properties good for families" filter to discover stays that feature amenities ideal for families on the move, such as living rooms, pools, entertainment units and bunk beds.
What are the top attractions for families in Chestertown?
You'll find loads of cool things to do and see with the family in Chestertown, such as:
  • Loon Lake Beach
  • Natural Stone Bridge and Caves
  • Friends Lake
Are there holiday homes with WiFi in Chestertown?
Chestertown has four holiday homes with WiFi, so you'll be able to stay connected while on holiday. Simply check the "WiFi" box in our search filter for a list of properties with this feature. From streaming movies with your family to posting pics on social media, these Bookabach homes make it easy to go online.
How can I find holiday homes with air conditioning in Chestertown?
Chestertown has 13 holiday homes where you can relax and recharge in air-conditioned comfort. To book a property on Bookabach featuring this amenity, choose your travel dates and use the convenient filters to select the "air conditioning" box.
How old do you have to be to rent a holiday home in Chestertown?
You should check with the Chestertown holiday property you'd like on Bookabach as the age limit differs. However, it's normally 16, 18 or 21.
How long can I rent a holiday home in Chestertown for?
The length of time you can book a holiday home in Chestertown depends on the property. Just enter your chosen travel dates to look at a list of options offering extended stays. With many creature comforts like full kitchens and air conditioning, as well as some offering weekly or monthly discounted prices, you're sure to discover a perfect place to call your home away from home in Chestertown.