Vacation Rentals in Silver Beach, NY: Compare 10+ Sites & Save

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609 Best Vacation Rentals in Silver Beach (Starting from $233)

Sandpoint by Rove Travel Modern 5BR Family Home with Pool
Sandpoint by Rove Travel Modern 5BR Family Home with Pool
House
Shelter Island, NY, USA
0.5k from Silver Beach center

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

1 Bedroom12 Guests
New to Booking
$1760
Average price / night
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5 minute walk to Crab Creek Beach.\nLarge yard and  pool for family fun.
5 minute walk to Crab Creek Beach.\nLarge yard and pool for family fun.
House
Shelter Island, NY, 11964, United States
0.1k from Silver Beach center

AC, Dryer, Heater, Internet, Laundry, No Smoking, Patio, Washer

3 Bedrooms8 Guests
New to Booking
$877
Average price / night
Check Availability
West Neck Guesthouse
West Neck Guesthouse
House
Shelter Island Heights, NY, USA
2.6k from Silver Beach center

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

6 Bedrooms8 Guests
8.9

Fabulous

17 reviews

$358
Average price / night
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Seaside Serenity: Newly renovated ocean breeze home - minutes' walk to the beach
Seaside Serenity: Newly renovated ocean breeze home - minutes' walk to the beach
House
Shelter Island Heights, NY, 11965, United States
0.3k from Silver Beach center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Laundry, Microwave, No Smoking

4 Bedrooms8 Guests
10.0

Exceptional

4 reviews

$1142
Average price / night
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Happiness Comes in Waves
Happiness Comes in Waves
House
Silver Beach, Shelter Island Heights, New York, USA
4.0k from Silver Beach center

Kitchen, Internet, Air Conditioner, Parking, Balcony/Terrace, Pet Friendly, Child Friendly

4 Bedrooms10 Guests
New to Booking
$438
Average price / night
Check Availability
Beautiful, quiet, private, short walk to the beach.
Beautiful, quiet, private, short walk to the beach.
House
Shelter Island, NY, 11964, United States
0.3k from Silver Beach center

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

3 Bedrooms6 Guests
10.0

Exceptional

93 reviews

$659
Average price / night
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Private Waterfront Home: Dock, Kayaks
Private Waterfront Home: Dock, Kayaks
House
Southold, NY, USA
4.9k from Silver Beach center

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

1 Bedroom6 Guests
New to Booking
$801
Average price / night
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Cozy Shelter Island all season Rental
Cozy Shelter Island all season Rental
House
Shelter Island, NY, 11964, United States
0.3k from Silver Beach center

AC, Barbecue, Crib, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Internet

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$685
Average price / night
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Private Waterfront home Dock Kayak walk to Southold, near Greenp
Private Waterfront home Dock Kayak walk to Southold, near Greenp
House
Silver Beach, Shelter Island Heights, New York, USA
4.9k from Silver Beach center

Parking, Child Friendly

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$389
Average price / night
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Waterfront Home Plus Separate Cottage/Dock
Waterfront Home Plus Separate Cottage/Dock
House
Shelter Island, NY, 11964, United States
0.4k from Silver Beach center

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

4 Bedrooms9 Guests
10.0

Exceptional

9 reviews

$1075
Average price / night
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Watersedge Retreat
Watersedge Retreat
House
Southold, NY, USA
5.0k from Silver Beach center

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

3 Bedrooms6 Guests
New to Booking
$811
Average price / night
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Sandpoint by Rove Travel | 6BR Family Home w/ Pool
Sandpoint by Rove Travel | 6BR Family Home w/ Pool
House
Shelter Island, NY, 11964, United States
0.5k from Silver Beach center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking

6 Bedrooms12 Guests
New to Booking
$1520
Average price / night
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Modern on 9th
Modern on 9th
House
Greenport, NY, USA
5.1k from Silver Beach center

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

3 Bedrooms6 Guests
New to Booking
$403
Average price / night
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Mid-Century Gem with Pool, Fireplace and Steps to Private Beach.
Mid-Century Gem with Pool, Fireplace and Steps to Private Beach.
House
Shelter Island, NY, 11964, United States
0.6k from Silver Beach center

AC, Dryer, Heater, Internet, Laundry, No Smoking, Washer

3 Bedrooms6 Guests
New to Booking
$686
Average price / night
Check Availability
Steve's Place: Heated Pool, 3BR Southold Home, Beach
Steve's Place: Heated Pool, 3BR Southold Home, Beach
House
Southold, NY, USA
5.3k from Silver Beach center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

3 Bedrooms6 Guests
New to Booking
$304
Average price / night
Check Availability
Explore the Hampton in this Shelter Island Getaway.  Weekly Bookings
Explore the Hampton in this Shelter Island Getaway. Weekly Bookings
House
Shelter Island, NY, 11964, United States
0.7k from Silver Beach center

AC, Barbecue, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Internet, Kitchen

3 Bedrooms6 Guests
10.0

Exceptional

13 reviews

$855
Average price / night
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Classic Southold Country Charmer
Classic Southold Country Charmer
House
Southold, NY, USA
5.4k from Silver Beach center

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

2 Bedrooms4 Guests
10.0

Exceptional

1 reviews

$233
Average price / night
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Stunning Waterfront Estate House with 270 degree sea views on 7 private acres
Stunning Waterfront Estate House with 270 degree sea views on 7 private acres
House
Shelter Island, NY, 11964, United States
0.7k from Silver Beach center

AC, Balcony, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Hot Tub, Internet

4 Bedrooms8 Guests
10.0

Exceptional

11 reviews

$1507
Average price / night
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Cozy Greenport Cottage
Cozy Greenport Cottage
House
Greenport, NY, USA
5.6k from Silver Beach center

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

3 Bedrooms10 Guests
New to Booking
$559
Average price / night
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Charming updated home with pool on quiet street.  Near Silver Beach
Charming updated home with pool on quiet street. Near Silver Beach
House
Shelter Island, NY, 11964, United States
0.7k from Silver Beach center

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

3 Bedrooms8 Guests
10.0

Exceptional

17 reviews

$534
Average price / night
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unbelievable water views, 50' heated pool and private beach
unbelievable water views, 50' heated pool and private beach
House
Shelter Island, NY, 11964, United States
0.8k from Silver Beach center

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

3 Bedrooms6 Guests
New to Booking
$955
Average price / night
Check Availability
Waterfront Charmer  with boat slip on idyllic Shelter Island for summer rental
Waterfront Charmer with boat slip on idyllic Shelter Island for summer rental
House
Shelter Island, NY, 11964, United States
0.8k from Silver Beach center

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

3 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$1463
Average price / night
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Private heated pool and spacious yard. 5 minute walk to the beach.
Private heated pool and spacious yard. 5 minute walk to the beach.
House
Shelter Island, NY, 11964, United States
0.8k from Silver Beach center

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

4 Bedrooms7 Guests
10.0

Exceptional

8 reviews

$1098
Average price / night
Check Availability
Shelter Island Retreat With Pool ...Close To Beach & Pet Friendly
Shelter Island Retreat With Pool ...Close To Beach & Pet Friendly
House
Shelter Island, NY, 11964, United States
0.8k from Silver Beach center

AC, Arcade, Barbecue, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Internet

3 Bedrooms9 Guests
10.0

Exceptional

16 reviews

$859
Average price / night
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Lovely Shelter Island cottage with panoramic bay views, secluded, screened...
Lovely Shelter Island cottage with panoramic bay views, secluded, screened...
House
Shelter Island, NY, 11964, United States
0.9k from Silver Beach center

AC, Barbecue, Crib, Dryer, Extra Bed, Fireplace, Free Parking, Heater, Kitchen

4 Bedrooms6 Guests
9.4

Superb

14 reviews

$638
Average price / night
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Shelter Island Waterfront Home!
Shelter Island Waterfront Home!
House
Shelter Island, NY, 11964, United States
1.0k from Silver Beach center

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

5 Bedrooms10 Guests
9.8

Exceptional

9 reviews

$860
Average price / night
Check Availability
Spectacular Waterfront-Best view on island-Tastefully renovated 1929 Cape.
Spectacular Waterfront-Best view on island-Tastefully renovated 1929 Cape.
House
Shelter Island, NY, 11964, United States
1.0k from Silver Beach center

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

4 Bedrooms8 Guests
10.0

Exceptional

8 reviews

$931
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 Silver Beach.

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Frequently Asked Questions

You can explore 609 verified vacation rentals in Silver Beach. 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 Silver Beach vary depending on the season, property size, and location. Rates typically start from around $233 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 Silver Beach 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 Silver Beach welcome pets. Currently, 36 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 Silver Beach often include amenities such as Fireplace/Heating, Laundry, and Balcony/Terrace. 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.