Chestertown holiday rentals

We found 302 holiday rentals — enter your dates for availability
Select from 50 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:4 Dec - 11 Dec

Children’s area
Exterior detail
Terrace/patio
Room
Wonderful
(88 reviews)

SKI TIME! Adirondack Waterfront Log Cabin

Warrensburg

8% off
S$6,448
for 7 nights, 1 cabin
S$921 per night
includes taxes & fees
SKI TIME! Adirondack Waterfront Log Cabin
Exterior
Private kitchen
Wooden table for 6-8 with comfortable chairs
Have a seat at the bar and cheer on your chef
Exceptional
(89 reviews)

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

Chestertown

8% off
S$3,768
for 7 nights, 1 chalet
S$538 per night
includes taxes & fees
Loon Lake, Chestertown - close to Gore: cozy, clean and bright chalet for 6-8
Warrensburg Vacation Rental | 5BR | 4.5BA | 3,000 Sq Ft | Stairs Required
Dining area
Screened porch
Interior
Exceptional
(12 reviews)

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

Warrensburg

6% off
S$10,982
for 7 nights, 1 cabin
S$1,569 per night
includes taxes & fees
Spacious log cabin in Warrensburg w/ Hot Tub: 15 Mi to Lake George
Living area
Dining
Private kitchen
Solitude
Very good
(46 reviews)

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

Warrensburg

7% off
S$4,555
for 7 nights, 1 cabin
S$651 per night
includes taxes & fees
Adirondack Rustic 2 Story- 10 ACRES-SKI, SKI, SKI!
Sunrise
Lake View House
Interior
Family room
Exceptional
(149 reviews)

Hickory Hill Mountaintop charming family friendly quiet very private lake view

Bolton Landing

8% off
S$8,824
for 7 nights, 1 home
S$1,261 per night
includes taxes & fees
Hickory Hill Mountaintop charming family friendly quiet very private lake view
Marina
Outdoor dining
Room
Exterior
Exceptional
(29 reviews)

Lake side Chalet Brant Lake w/ outdoor Hot Tub

Brant Lake

8% off
S$5,036
for 7 nights, 1 home
S$719 per night
includes taxes & fees
Lake side Chalet Brant Lake w/ outdoor Hot Tub
Super comfortable futon.
Outdoor dining
Dining
Exterior
Exceptional
(43 reviews)

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

Schroon Lake

7% off
S$4,460
for 7 nights, 1 cabin
S$637 per night
includes taxes & fees
The perfect ADK log cabin getaway on 4 acres and 5 min. to town!
Living area
Interior
Dining
Exterior
Exceptional
(43 reviews)

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

Chestertown

9% off
S$3,084
for 7 nights, 1 room
S$441 per night
includes taxes & fees
Modern Cabin w/ Hot Tub-Minutes to Lakes & Skiing
Open concept living space
Gas grill with a water view
Screened balcony off of Master Bedroom
Master bedroom - King bed, smart TV, private lake view balcony
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

11% off
S$2,006
for 7 nights, 1 home
S$287 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.
Private kitchen
Outdoor dining
Room
Interior
Exceptional
(11 reviews)

Cozy lil' Cabin in the Adirondacks with fireplace.

North Creek

8% off
S$1,880
for 7 nights, 1 home
S$269 per night
includes taxes & fees
Cozy lil' Cabin in the Adirondacks with fireplace.
GORE Close by -11 minute drive
Post Beam Barn and a fire pit.
Vaulted Ceiling kitchen, Fresh, Clean, Renovated
To the Living Room. Leather/2 leather Mission oak Recliners for your comfort
Exceptional
(59 reviews)

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

Wevertown

8% off
S$3,241
for 7 nights, 1 home
S$463 per night
includes taxes & fees
Near The Black Hole, swim, SKI GORE nearby, Walking trail,Trout stream, Hiking,
Front Entry
Rear patio fire pit
Exterior
Private kitchen
Exceptional
(26 reviews)

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

Bolton Landing

8% off
S$15,171
for 7 nights, 1 home
S$2,167 per night
includes taxes & fees
The Bolton House - 5 BR 3.5 BA Home with Hot Tub
Master bedroom
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
S$3,163
for 7 nights, 1 home
S$452 per night
includes taxes & fees
Adirondack home, near Gore Mt ski resort, North Creek, and Loon lake.
Gather the friends and family around the table for good food and games.
Private oasis.
Entry.
Patio.
Wonderful
(15 reviews)

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

Pottersville

12% off
S$1,936
for 7 nights, 1 cabin
S$277 per night
includes taxes & fees
Vintage ADK Cabin- Great Deal, Perfect Location, book your Gore Mtn. trip today!
Fireplace and kitchen open up to the dining area and great room.
Life is about who you spend your time with.  In the great room - only smiles!
Relax in the great room, in classic Adirondack style!
King beds in all of the high ceilinged bedrooms.
Exceptional
(6 reviews)

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

Chestertown

8% off
S$2,862
for 7 nights, 1 apartment
S$409 per night
includes taxes & fees
Our property has sold! Contact us to direct you to the new owner's VRBO listing!
The Lodge at Birchwood Cottages at Loon Lake 8-2018
2018 New sitting area around fire pit
Living room
Lodge entryway, looking towards living room.
Exceptional
(57 reviews)

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

Chestertown

7% off
S$4,511
for 7 nights, 1 home
S$644 per night
includes taxes & fees
Lakefront spacious contemporary. Large families welcome. Ski GORE nearby!
Cabin
Deck and View
Dining Room and Kitchen
Living Room
Exceptional
(47 reviews)

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

Johnsburg

8% off
S$6,527
for 7 nights, 1 home
S$932 per night
includes taxes & fees
Private Cabin with Mt View & hot-tub. Near Gore, Placid & Lake George. Sleeps 15
Balcony
Gas Fireplace
Kitchen
Dining Room
Exceptional
(109 reviews)

Secluded and Cozy Townhome at Tripp Lake

Chestertown

11% off
S$2,282
for 7 nights, 1 home
S$326 per night
includes taxes & fees
Secluded and Cozy Townhome at Tripp Lake
Room
Interior
Interior
Private kitchen
Exceptional
(50 reviews)

Rustic Adirondack Retreat on Tripp Lake

Chestertown

7% off
S$2,160
for 7 nights, 1 home
S$309 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)
  • Great Escape (21.6 mi / 34.7 km)
  • Hiland Park 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:

  • 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)
  • Hearthstone Point Campground (14.6 mi / 23.6 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 rental accommodation in Chestertown?
The most sought-after types of holiday rentals in Chestertown are houses. Want something different? Vrbo 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 rental 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 rental. Put in your Chestertown travel dates to see all your options on Vrbo. Can't live without a private pool? Use our filters to select the features and amenities you want.
Are there pet-friendly holiday rentals in Chestertown?
You're in luck. There are. Take your pick of 14 stays that welcome pets in Chestertown on Vrbo. Our furry companions also need a break, so simply use our search function for pet-friendly holiday rentals to find a pad where Rover can join the fun.
What are popular rental amenities in Chestertown?
Tennis, an electric car charging station and nearby museums rank as the most popular rental amenities in Chestertown. Whether you're travelling alone, with your significant other or a group of dear friends, Vrbo will help you find a holiday rental that matches your tastes with all the features you're looking for.
Are there large group holiday rentals 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 rentals 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 rentals with WiFi in Chestertown?
Chestertown has four holiday rentals 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 Vrbo homes make it easy to go online.
How can I find holiday rentals with air conditioning in Chestertown?
Chestertown has 13 holiday rentals where you can relax and recharge in air-conditioned comfort. To book a property on Vrbo 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 rental in Chestertown?
You should check with the Chestertown holiday property you'd like on Vrbo as the age limit differs. However, it's normally 16, 18 or 21.
How long can I rent a holiday rental in Chestertown for?
The length of time you can book a holiday rental 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.

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