Vacation Rentals in Chester Shores, NY: Compare 10+ Sites & Save

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153 Best Vacation Rentals in Chester Shores (Starting from $151)

Lakeside Vibes
Lakeside Vibes
House
Chestertown, NY, USA
0.2k from Chester Shores center

Accommodations, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Beach, Places to stay, Beach rentals

3 Bedrooms4 Guests
New to Booking
$407
Average price / night
Check Availability
Loon Lake, Chestertown - spotless, bright chalet for  6-8, close to Public Beach
Loon Lake, Chestertown - spotless, bright chalet for 6-8, close to Public Beach
Ski Chalet
Chestertown, NY, 12817, United States
0.1k from Chester Shores center

AC, Arcade, Balcony, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater

4 Bedrooms8 Guests
10.0

Exceptional

87 reviews

$376
Average price / night
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Loon Lake View Newly Built Log Cabin with Fire Pit!
Loon Lake View Newly Built Log Cabin with Fire Pit!
House
Chestertown, NY, USA
0.3k from Chester Shores center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

2 Bedrooms6 Guests
New to Booking
$462
Average price / night
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Lakefront Home with WiFi, Dock, Lake Views From the Deck, and Screened-In Porch
Lakefront Home with WiFi, Dock, Lake Views From the Deck, and Screened-In Porch
House
Chestertown, NY, 12817, United States
0.2k from Chester Shores center

Free Parking, Internet, Kitchen, Living Area, Microwave, No Smoking, Outdoor Space, Patio, TV

3 Bedrooms6 Guests
8.6

Fabulous

19 reviews

$533
Average price / night
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Chestertown Hideaway with Lake and Beach Access!
Chestertown Hideaway with Lake and Beach Access!
House
Chestertown, NY, USA
1.6k from Chester Shores center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

3 Bedrooms8 Guests
8.7

Fabulous

4 reviews

$407
Average price / night
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Private Waterfront House on Loon Lake w Amazing Views- 20 Min Lake George & Gore
Private Waterfront House on Loon Lake w Amazing Views- 20 Min Lake George & Gore
House
Chestertown, NY, 12817, United States
0.2k from Chester Shores center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms8 Guests
9.4

Superb

30 reviews

$355
Average price / night
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Basic Adirondack Camp
Basic Adirondack Camp
House
Chestertown, NY, USA
1.7k from Chester Shores center

Cheap, Accommodations, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals, Places to stay

3 Bedrooms6 Guests
9.0

Fabulous

2 reviews

$375
Average price / night
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Lakefront Home - 20 Min from Gore Mountain w/Hot Tub
Lakefront Home - 20 Min from Gore Mountain w/Hot Tub
House
Chestertown, NY, 12817, United States
0.2k from Chester Shores center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet, Kitchen

4 Bedrooms10 Guests
10.0

Exceptional

10 reviews

$587
Average price / night
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Hunerburg White House
Hunerburg White House
House
Chestertown, NY, USA
2.4k from Chester Shores center

Accommodations, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay, Accessible hotels

3 Bedrooms6 Guests
New to Booking
$330
Average price / night
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Same local favorite, an even better nightly rate, and now with NO CLEANING FEE!
Same local favorite, an even better nightly rate, and now with NO CLEANING FEE!
House
Chestertown, NY, 12817, United States
0.3k from Chester Shores center

AC, Arcade, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet

4 Bedrooms9 Guests
10.0

Exceptional

36 reviews

$471
Average price / night
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Two Houses on One Magnificent Property
Two Houses on One Magnificent Property
House
Chester Shores, Chestertown, New York, USA
2.4k from Chester Shores center

Kitchen, Private Beach, Ocean View, View, Balcony/Terrace, Parking, Internet

4 Bedrooms8 Guests
New to Booking
$632
Average price / night
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Serene Loon Lake Waterfront - Sleeps up to 10
Serene Loon Lake Waterfront - Sleeps up to 10
House
Chestertown, NY, 12817, United States
0.4k from Chester Shores center

AC, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

4 Bedrooms10 Guests
10.0

Exceptional

7 reviews

$576
Average price / night
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The Lily Pad at Loon Lake near Gore Mountain
The Lily Pad at Loon Lake near Gore Mountain
House
Chestertown, NY, USA
2.5k from Chester Shores center

Accommodations, Villas, Vacation homes, Cottages, Lodgings, Places to stay

4 Bedrooms11 Guests
New to Booking
$291
Average price / night
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Family Friendly Cabin—Lake Views, Modern Luxe Escape by Gore Mtn, Adirondacks
Family Friendly Cabin—Lake Views, Modern Luxe Escape by Gore Mtn, Adirondacks
Cabin
Chestertown, NY, 12817, United States
0.4k from Chester Shores center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms8 Guests
New to Booking
$434
Average price / night
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Lily Pad North at Loon Lake near Gore Mountain
Lily Pad North at Loon Lake near Gore Mountain
Apartment
Chestertown, NY, USA
2.5k from Chester Shores center

Fireplace/Heating, Guest Services, Internet, View, Security/Safety, Air Conditioner, Child Friendly

2 Bedrooms6 Guests
New to Booking
$151
Average price / night
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Loon Lake Chalet with HOT TUB,kayaks, canoe, Close to Gore Mnt and Lake George
Loon Lake Chalet with HOT TUB,kayaks, canoe, Close to Gore Mnt and Lake George
Ski Chalet
Chestertown, NY, 12817, United States
0.4k from Chester Shores center

Barbecue, Dryer, Free Parking, Heater, Hot Tub, Internet, Laundry, Living Area, Microwave

3 Bedrooms8 Guests
New to Booking
$481
Average price / night
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Sagevick Cabin
Sagevick Cabin
House
Chestertown, NY, USA
2.5k from Chester Shores center

Accommodations, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Beach, Places to stay, Beach rentals

1 Bedroom2 Guests
New to Booking
$236
Average price / night
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4 BR modern farmhouse with 173 ft of private lakefront on tranquil Loon Lake.
4 BR modern farmhouse with 173 ft of private lakefront on tranquil Loon Lake.
House
Chestertown, NY, 12817, United States
0.5k from Chester Shores center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, No Smoking, Outdoor Space

4 Bedrooms10 Guests
New to Booking
$542
Average price / night
Check Availability
Moonbeams & Fireflies
Moonbeams & Fireflies
House
Chestertown, NY, USA
2.5k from Chester Shores center

Accommodations, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Beach, Places to stay, Beach rentals

5 Bedrooms10 Guests
8.3

Very Good

3 reviews

$335
Average price / night
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Lower Chalet, Gore Mountain Skiing, Pool/AC/Woodstove, Cozy Cabin, Loon Lake.
Lower Chalet, Gore Mountain Skiing, Pool/AC/Woodstove, Cozy Cabin, Loon Lake.
Cabin
Chestertown, NY, 12817, United States
0.6k from Chester Shores center

AC, Arcade, Barbecue, Fireplace, Free Parking, Heater, Internet, Kitchen, Microwave

2 Bedrooms4 Guests
8.6

Fabulous

8 reviews

$295
Average price / night
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Eagles Nest at Loon Lake near Gore Mountain
Eagles Nest at Loon Lake near Gore Mountain
House
Chestertown, NY, USA
2.6k from Chester Shores center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

1 Bedroom16 Guests
New to Booking
$452
Average price / night
Check Availability
Lakefront home steps away from a private, gentle sloping sandy beach & fire pit.
Lakefront home steps away from a private, gentle sloping sandy beach & fire pit.
House
Chestertown, NY, 12817, United States
0.7k from Chester Shores center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

4 Bedrooms8 Guests
10.0

Exceptional

43 reviews

$899
Average price / night
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Rustic Adirondacks Home with Hot Tub and Lake Access!
Rustic Adirondacks Home with Hot Tub and Lake Access!
House
Chestertown, NY, USA
2.6k from Chester Shores center

Cheap, Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals

3 Bedrooms8 Guests
10.0

Exceptional

4 reviews

$422
Average price / night
Check Availability
Hide-A-Way Cabin, Pool & AC, Authetic Adirondack Cabin Steps from Loon Lake
Hide-A-Way Cabin, Pool & AC, Authetic Adirondack Cabin Steps from Loon Lake
House
Chestertown, NY, 12817, United States
0.7k from Chester Shores center

AC, Arcade, Barbecue, Fireplace, Free Parking, Heater, Internet, Kitchen, Living Area

1 Bedroom2 Guests
9.4

Superb

3 reviews

$264
Average price / night
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Loon's Lair, A Beautiful immaculate Adirondack 2 Bedroom 3 Bathroom Suite
Loon's Lair, A Beautiful immaculate Adirondack 2 Bedroom 3 Bathroom Suite
Apartment
Chestertown, NY, 12817, United States
0.8k from Chester Shores center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

2 Bedrooms6 Guests
9.0

Fabulous

4 reviews

$225
Average price / night
Check Availability
Unique Lakefront House with Sandy Beach and Dock - Sweeping Views
Unique Lakefront House with Sandy Beach and Dock - Sweeping Views
House
Chestertown, NY, 12817, United States
0.8k from Chester Shores center

Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Kitchen, Laundry, Living Area

4 Bedrooms8 Guests
8.6

Fabulous

4 reviews

$862
Average price / night
Check Availability
Bass Bunk, A Beautiful Loon Lake Family Cabin in the Adirondack Mountains
Bass Bunk, A Beautiful Loon Lake Family Cabin in the Adirondack Mountains
Cabin
Chestertown, NY, 12817, United States
0.8k from Chester Shores center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms6 Guests
9.2

Superb

10 reviews

$275
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals in Chester Shores.

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Frequently Asked Questions

You can explore 153 verified vacation rentals in Chester Shores. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in Chester Shores vary depending on the season, property size, and location. Rates typically start from around $151 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in Chester Shores include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in Chester Shores welcome pets. Currently, 21 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it’s recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in Chester Shores often include amenities such as Fireplace/Heating, Barbecue/Outdoor Cooking, and Child Friendly. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.