Oceanfront Rentals in Shelter Island Historical Society, NY: Compare 10+ Sites & Save

AirbnbBooking.comVrboExpediaKayakTripadvisorHotels.comAgoda.com
  1. VBOR
  2. Oceanfront Rentals
  3.  USA

  4.  New York

  5.  Shelter Island
  6.  Shelter Island Historical Society

Refine your search

Price per night

Amenity Filter

Rating

244 Best Oceanfront Rentals in Shelter Island Historical Society (Starting from $236)

Shelter Island Retreat with Outdoor Pool!
Shelter Island Retreat with Outdoor Pool!
House
Shelter Island, NY, USA
4.5k from Shelter Island Historical Society center

Cheap, Accommodations, Pools, Parking, Villas, Vacation homes, Spa, Cottages, Lodgings

5 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$1119
Average price / night
Check Availability
Charming, Historic Cottage
Charming, Historic Cottage
Cottage
Shelter Island, NY, 11964, United States
0.8k from Shelter Island Historical Society center

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

3 Bedrooms6 Guests
10.0

Exceptional

4 reviews

$752
Average price / night
Check Availability
Bright Apartment - half Mi to Greenport Harbor!
Bright Apartment - half Mi to Greenport Harbor!
Apartment
Greenport, NY, USA
5.1k from Shelter Island Historical Society center

Apartments, Accommodations, Parking, Spa, Lodgings, Vacation rentals, Places to stay, Family

1 Bedroom2 Guests
9.8

Exceptional

14 reviews

$236
Average price / night
Check Availability
Beautiful Shelter Island Getaway on over an acre, minutes from the ferry!
Beautiful Shelter Island Getaway on over an acre, minutes from the ferry!
House
Shelter Island, NY, 11964, United States
0.9k from Shelter Island Historical Society center

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

5 Bedrooms10 Guests
New to Booking
$972
Average price / night
Check Availability
Lagoon Lodge: North Fork,Charming 3Br, Waterfront
Lagoon Lodge: North Fork,Charming 3Br, Waterfront
House
East Marion, NY, USA
6.1k from Shelter Island Historical Society center

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

3 Bedrooms8 Guests
New to Booking
$550
Average price / night
Check Availability
Chic Shelter Island A-Frame with Private Pool, Stylish Interiors, and...
Chic Shelter Island A-Frame with Private Pool, Stylish Interiors, and...
House
Shelter Island, NY, 11964, United States
0.9k from Shelter Island Historical Society center

AC, Dryer, Free Parking, Heater, Kitchen, No Smoking, Patio, Pool, TV

3 Bedrooms6 Guests
New to Booking
$997
Average price / night
Check Availability
The Cliffside Resort Condominiums
The Cliffside Resort Condominiums
Apartment
Greenport, NY, USA
6.3k from Shelter Island Historical Society center

Apartments, Cheap, Accommodations, Pools, Parking, 3-star, Lodgings, Vacation rentals, Beach

130 Bedrooms391 Guests
8.6

Fabulous

233 reviews

$405
Average price / night
Check Availability
Private wooded summer house 5 minute walk to Wades Beach
Private wooded summer house 5 minute walk to Wades Beach
House
Shelter Island, NY, 11964, United States
0.9k from Shelter Island Historical Society center

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

4 Bedrooms6 Guests
10.0

Exceptional

28 reviews

$773
Average price / night
Check Availability
Watersedge Retreat
Watersedge Retreat
House
Southold, NY, USA
7.9k from Shelter Island Historical Society 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
Check Availability
Work and Play Special!  Extended Stay Discount
Work and Play Special! Extended Stay Discount
House
Shelter Island, NY, 11964, United States
1.4k from Shelter Island Historical Society center

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

5 Bedrooms10 Guests
10.0

Exceptional

53 reviews

$1308
Average price / night
Check Availability
Villa Ebrar - Luxury with pool
Villa Ebrar - Luxury with pool
Villa
Sag Harbor, NY, USA
8.3k from Shelter Island Historical Society center

Luxury, Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals

4 Bedrooms8 Guests
New to Booking
$500
Average price / night
Check Availability
Shelter Island Retreat, 5 bdrms near everything!
Shelter Island Retreat, 5 bdrms near everything!
House
Shelter Island, NY, 11964, United States
1.4k from Shelter Island Historical Society center

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

5 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$834
Average price / night
Check Availability
queeen room
queeen room
House
Shelter Island Historical Society, Shelter Island, New York, USA
8.3k from Shelter Island Historical Society center

Internet, Oceanfront, Balcony/Terrace, View, Ocean View, Air Conditioner, Private Beach

1 Bedroom3 Guests
9.0

Fabulous

1 reviews

$270
Average price / night
Check Availability
Charming Studio on Shelter Island
Charming Studio on Shelter Island
Apartment
Shelter Island, NY, 11964, United States
1.6k from Shelter Island Historical Society center

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

1 Bedroom2 Guests
New to Booking
$371
Average price / night
Check Availability
Villa KeyLime
Villa KeyLime
Villa
Sag Harbor, NY, USA
8.7k from Shelter Island Historical Society center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Beach

5 Bedrooms9 Guests
New to Booking
$1241
Average price / night
Check Availability
Waterfront House With Dock And Private Beach
Waterfront House With Dock And Private Beach
House
Shelter Island, NY, 11964, United States
1.7k from Shelter Island Historical Society center

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

3 Bedrooms6 Guests
10.0

Exceptional

22 reviews

$740
Average price / night
Check Availability
Bright Oasis in Beautiful North Fork Wine Country
Bright Oasis in Beautiful North Fork Wine Country
House
Southold, NY, USA
8.9k from Shelter Island Historical Society center

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

4 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$391
Average price / night
Check Availability
WATERFRONT with Private Beach Boat Dock and Launch Ramp
WATERFRONT with Private Beach Boat Dock and Launch Ramp
House
Shelter Island, NY, 11964, United States
1.7k from Shelter Island Historical Society center

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

2 Bedrooms6 Guests
10.0

Exceptional

6 reviews

$1060
Average price / night
Check Availability
NF Wine Country Retreat with Dock
NF Wine Country Retreat with Dock
House
Southold, NY, USA
8.9k from Shelter Island Historical Society center

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

1 Bedroom8 Guests
New to Booking
$499
Average price / night
Check Availability
Waterfront Victorian farmhouse with heated pool and deepwater dock
Waterfront Victorian farmhouse with heated pool and deepwater dock
House
Shelter Island, NY, 11964, United States
1.7k from Shelter Island Historical Society center

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

6 Bedrooms16 Guests
New to Booking
$1723
Average price / night
Check Availability
 Ideal for 2 families, private,  pool, close to beaches and marina  Sleeps 12
Ideal for 2 families, private, pool, close to beaches and marina Sleeps 12
House
Shelter Island, NY, 11964, United States
1.7k from Shelter Island Historical Society center

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

6 Bedrooms12 Guests
10.0

Exceptional

1 reviews

$1042
Average price / night
Check Availability
Waterfront Home on Beautiful Shelter Island w/Large Deep Water Dock
Waterfront Home on Beautiful Shelter Island w/Large Deep Water Dock
House
Shelter Island, NY, 11964, United States
1.8k from Shelter Island Historical Society center

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

5 Bedrooms12 Guests
9.6

Exceptional

13 reviews

$1116
Average price / night
Check Availability
Relaxing Shelter Island Getaway - great for families and couples!
Relaxing Shelter Island Getaway - great for families and couples!
House
Shelter Island Heights, NY, 11965, United States
1.8k from Shelter Island Historical Society center

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

3 Bedrooms6 Guests
9.8

Exceptional

43 reviews

$318
Average price / night
Check Availability
Peaceful and Private Shelter Island Getaway
Peaceful and Private Shelter Island Getaway
House
Shelter Island, NY, 11964, United States
1.9k from Shelter Island Historical Society center

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

3 Bedrooms5 Guests
10.0

Exceptional

52 reviews

$402
Average price / night
Check Availability
Tranquility Base; Architect-Renovated, Modern Ranch With Heated Pool
Tranquility Base; Architect-Renovated, Modern Ranch With Heated Pool
House
Shelter Island, NY, 11964, United States
1.9k from Shelter Island Historical Society center

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

4 Bedrooms8 Guests
10.0

Exceptional

30 reviews

$1035
Average price / night
Check Availability
 Shelter Island Tranquil Modern Barn on Private Acre to Rest & Renew All Year
Shelter Island Tranquil Modern Barn on Private Acre to Rest & Renew All Year
House
Shelter Island Heights, NY, 11964, United States
2.2k from Shelter Island Historical Society center

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

3 Bedrooms6 Guests
9.4

Superb

6 reviews

$931
Average price / night
Check Availability
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
2.2k from Shelter Island Historical Society 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
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 Oceanfront Rentals in Shelter Island Historical Society.

Where to stay in Shelter Island Historical Society? Best neighborhoods & areas

Shelter Island Historical Society Oceanfront Rentals on the Map

Frequently Asked Questions

You can explore 244 verified oceanfront rentals in Shelter Island Historical Society. These properties are located directly along the shoreline, offering uninterrupted access to the beach and ocean views.

Oceanfront rental prices in Shelter Island Historical Society vary depending on the property size, exact beachfront location, and season. Rates typically start from around $236 per night, with higher prices for larger homes or peak travel periods. Properties located directly on popular stretches of coastline tend to command premium rates.

Many oceanfront rentals in Shelter Island Historical Society offer direct access to the beach, often through private walkways or dedicated entry paths. Some properties may share access points, so it’s helpful to review the listing details to understand the type of beach access provided.

Yes, some oceanfront rentals in Shelter Island Historical Society welcome pets. Currently, 28 listings allow pets, although policies can vary by property. It’s recommended to check specific house rules for details such as size limits or additional fees.

Oceanfront properties are often in high demand, especially during peak travel seasons, so booking 90 to 120 days in advance is recommended for the best selection. During quieter periods, you may still find availability closer to your travel dates.

Oceanfront rentals in Shelter Island Historical Society often include features designed for a comfortable coastal stay, such as Oceanfront, Ocean View, and View. These amenities help guests make the most of their time by the water.

Yes, there is a clear difference. "Oceanfront" means the property is located directly on the beach with no obstructions between the home and the water. "Ocean View" typically means the ocean is visible from certain angles or rooms, but the property may not be right on the shoreline.