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

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28 Beach Home Rentals in Chester Shores (Starting from $171)

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
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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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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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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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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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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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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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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
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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
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Sleepy Hollow,  Gore Mountain, Pool, AC, Fireplace, close to Loon Lake
Sleepy Hollow, Gore Mountain, Pool, AC, Fireplace, close to Loon Lake
House
Chestertown, NY, 12817, United States
0.9k from Chester Shores center

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

3 Bedrooms6 Guests
9.8

Exceptional

7 reviews

$385
Average price / night
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Log Haven Cabin, Gore Skiing, Pool/AC/Fireplace, Steps to Loon Lake
Log Haven Cabin, Gore Skiing, Pool/AC/Fireplace, Steps to Loon Lake
Cabin
Chestertown, NY, 12817, United States
0.9k from Chester Shores center

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

2 Bedrooms4 Guests
9.6

Exceptional

22 reviews

$306
Average price / night
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Newly Renovated 3 BRD, 2 BA chalet on 50 acres.  Easy access to Loon Lake/Gore
Newly Renovated 3 BRD, 2 BA chalet on 50 acres. Easy access to Loon Lake/Gore
House
Chestertown, NY, 12817, United States
1.1k from Chester Shores center

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

3 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$539
Average price / night
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WaterFront Adirondack Home-located between Gore and Lake George
WaterFront Adirondack Home-located between Gore and Lake George
House
Chestertown, NY, 12817, United States
1.2k from Chester Shores center

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

4 Bedrooms14 Guests
10.0

Exceptional

15 reviews

$666
Average price / night
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New Adirondack spacious cabin in the Lake George and Gore Mountain Area
New Adirondack spacious cabin in the Lake George and Gore Mountain Area
Cabin
Chestertown, NY, 12817, United States
1.4k from Chester Shores center

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

3 Bedrooms9 Guests
9.8

Exceptional

6 reviews

$712
Average price / night
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Lakefront Cottage with Screened Gazebo, Dock, and Two Acres of Space
Lakefront Cottage with Screened Gazebo, Dock, and Two Acres of Space
House
Chestertown, NY, 12817, United States
2.4k from Chester Shores center

Barbecue, Dryer, Free Parking, Kitchen, Laundry, Living Area, Microwave, No Smoking, Outdoor Space

3 Bedrooms6 Guests
9.6

Exceptional

7 reviews

$329
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, 12817, United States
2.5k from Chester Shores center

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

7 Bedrooms22 Guests
10.0

Exceptional

118 reviews

$450
Average price / night
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Lakefront cabin with beautiful loft, game room, views, private dock
Lakefront cabin with beautiful loft, game room, views, private dock
House
Chestertown, NY, 12817, United States
2.5k from Chester Shores center

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

5 Bedrooms10 Guests
9.2

Superb

50 reviews

$376
Average price / night
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Lakefront cabin with beautiful views, lake and beach access
Lakefront cabin with beautiful views, lake and beach access
House
Chestertown, NY, 12817, United States
2.5k from Chester Shores center

Barbecue, Extra Bed, Free Parking, Heater, Kitchen, Laundry, Living Area, Microwave, No Smoking

1 Bedroom2 Guests
9.6

Exceptional

13 reviews

$242
Average price / night
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NEW for 2024, 6 person hot tub. Spacious country home with large back yard.
NEW for 2024, 6 person hot tub. Spacious country home with large back yard.
House
Chestertown, NY, 12817, United States
2.5k from Chester Shores center

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

3 Bedrooms6 Guests
10.0

Exceptional

23 reviews

$302
Average price / night
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Private Adirondack lakefront Cottage on Loon Lake
Private Adirondack lakefront Cottage on Loon Lake
Cottage
Chestertown, NY, 12817, United States
2.5k from Chester Shores center

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

2 Bedrooms4 Guests
10.0

Exceptional

12 reviews

$250
Average price / night
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#6 Lakeview @Birchwood Cottages at Loon Lake. Family Friendly Waterfront
#6 Lakeview @Birchwood Cottages at Loon Lake. Family Friendly Waterfront
Cottage
Chestertown, NY, 12817, United States
2.6k from Chester Shores center

Arcade, Barbecue, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave, No Smoking

4 Bedrooms6 Guests
9.6

Exceptional

14 reviews

$216
Average price / night
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#7 Adirondack@Birchwood Cottages on Loon Lake. Family Friendly Waterfront
#7 Adirondack@Birchwood Cottages on Loon Lake. Family Friendly Waterfront
Cottage
Chestertown, NY, 12817, United States
2.6k from Chester Shores center

Arcade, Barbecue, Extra Bed, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave

3 Bedrooms6 Guests
10.0

Exceptional

4 reviews

$239
Average price / night
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#5 Adirondack FamilyFriendly Waterfront on LoonLake. Boating,fishing,swimming!
#5 Adirondack FamilyFriendly Waterfront on LoonLake. Boating,fishing,swimming!
Cottage
Chestertown, NY, 12817, United States
2.6k from Chester Shores center

Arcade, Barbecue, Extra Bed, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave

4 Bedrooms6 Guests
8.6

Fabulous

10 reviews

$216
Average price / night
Check Availability
Lakefront spacious contemporary. Large families welcome. Ski GORE nearby!
Lakefront spacious contemporary. Large families welcome. Ski GORE nearby!
House
Chestertown, NY, 12817, United States
2.6k from Chester Shores center

Arcade, Balcony, Barbecue, Dryer, Extra Bed, Fireplace, Free Parking, Heater, Internet

4 Bedrooms14 Guests
9.8

Exceptional

56 reviews

$500
Average price / night
Check Availability
#2 Adirondack FamilyFriendly Waterfront on LoonLake. Boating,fishing,swimming!
#2 Adirondack FamilyFriendly Waterfront on LoonLake. Boating,fishing,swimming!
Cottage
Chestertown, NY, 12817, United States
2.6k from Chester Shores center

Arcade, Barbecue, Extra Bed, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave

3 Bedrooms4 Guests
9.6

Exceptional

12 reviews

$171
Average price / night
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#3 Chester @ Birchwood Cottages at Loon Lake. Family Friendly Waterfront
#3 Chester @ Birchwood Cottages at Loon Lake. Family Friendly Waterfront
Cottage
Chestertown, NY, 12817, United States
2.6k from Chester Shores center

Arcade, Barbecue, Extra Bed, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking

3 Bedrooms5 Guests
8.4

Very Good

6 reviews

$178
Average price / night
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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 Beach Rentals in Chester Shores.

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Frequently Asked Questions

You can explore 28 verified beach rentals in Chester Shores. Our listings are sourced from trusted booking providers, giving you access to a wide selection of oceanfront homes, seaside condos, and coastal stays—all in one place.

Beach rental prices in Chester Shores vary depending on the season, property size, and distance from the shoreline. Rates typically start from around $171 per night, with beachfront properties and peak summer dates often priced higher. Comparing available options can help you find the best fit for your budget.

Many beach rentals in Chester Shores offer direct access to the sand or are located within a short walking distance of the shoreline. You can use filters to find properties with beachfront locations, private walkways, or unobstructed ocean views.

Yes, many beach rentals in Chester Shores welcome pets. Currently, 9 listings allow pets, although policies may vary by property. It’s also a good idea to check local beach regulations for any restrictions on pets during your stay.

For peak travel periods such as summer holidays or spring break, it’s recommended to book your beach rental 90 to 120 days in advance to secure the best options. During off-peak seasons, you may find more flexibility and availability closer to your travel dates.

Beach rentals in Chester Shores often include amenities designed for coastal living, such as Ocean View, View, and Fireplace/Heating. These features help enhance comfort and make it easier to enjoy time by the water.

Some beach rentals provide extras like chairs, umbrellas, or beach gear, but this can vary by property. It’s best to review the amenities section of each listing to confirm what is included and plan accordingly.