Oceanfront Rentals in Dering Harbor, NY: Compare 10+ Sites & Save

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158 Best Oceanfront Rentals in Dering Harbor (Starting from $236)

Bright Apartment - half Mi to Greenport Harbor!
Bright Apartment - half Mi to Greenport Harbor!
Apartment
Greenport, NY, USA
1.9k from Dering Harbor center

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

1 Bedroom2 Guests
9.8

Exceptional

14 reviews

$236
Average price / night
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Spacious Modern on wooded lot - 5 min from beach!
Spacious Modern on wooded lot - 5 min from beach!
House
Shelter Island, NY, 11964, United States
0.4k from Dering Harbor center

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

4 Bedrooms8 Guests
New to Booking
$793
Average price / night
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Lagoon Lodge: North Fork,Charming 3Br, Waterfront
Lagoon Lodge: North Fork,Charming 3Br, Waterfront
House
East Marion, NY, USA
2.9k from Dering Harbor center

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

3 Bedrooms8 Guests
New to Booking
$550
Average price / night
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Tranquil, Beachfront Getaway with Dock, Fabulous Sunset Views!
Tranquil, Beachfront Getaway with Dock, Fabulous Sunset Views!
House
Shelter Island, NY, 11964, United States
1.0k from Dering Harbor center

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

4 Bedrooms8 Guests
9.8

Exceptional

22 reviews

$584
Average price / night
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The Cliffside Resort Condominiums
The Cliffside Resort Condominiums
Apartment
Greenport, NY, USA
4.1k from Dering Harbor center

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

130 Bedrooms391 Guests
8.6

Fabulous

233 reviews

$405
Average price / night
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Tennis Court, Open and Spacious Living and Dining Areas, Close Proximity to...
Tennis Court, Open and Spacious Living and Dining Areas, Close Proximity to...
House
Shelter Island, NY, 11964, United States
1.2k from Dering Harbor center

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

5 Bedrooms10 Guests
New to Booking
$1470
Average price / night
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Shelter Island Retreat with Outdoor Pool!
Shelter Island Retreat with Outdoor Pool!
House
Shelter Island, NY, USA
5.6k from Dering Harbor center

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

5 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$1119
Average price / night
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Family friendly home near beach with wonderful deck!
Family friendly home near beach with wonderful deck!
House
Shelter Island, NY, 11964, United States
1.4k from Dering Harbor center

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

4 Bedrooms8 Guests
9.8

Exceptional

16 reviews

$677
Average price / night
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Watersedge Retreat
Watersedge Retreat
House
Southold, NY, USA
9.2k from Dering Harbor 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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Impeccably Restored & Charming Victorian Summer Cottage-5 Bed, 4 Bath, Sleeps 10
Impeccably Restored & Charming Victorian Summer Cottage-5 Bed, 4 Bath, Sleeps 10
House
Shelter Island Heights, NY, 11965, United States
1.4k from Dering Harbor center

AC, Barbecue, Dryer, Free Parking, Internet, Kitchen, Laundry, Living Area, No Smoking

5 Bedrooms10 Guests
10.0

Exceptional

2 reviews

$1123
Average price / night
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Bright Oasis in Beautiful North Fork Wine Country
Bright Oasis in Beautiful North Fork Wine Country
House
Southold, NY, USA
9.4k from Dering Harbor 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
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Bright and Spacious Summer Home Steps from the Beach
Bright and Spacious Summer Home Steps from the Beach
House
Shelter Island, NY, 11965, United States
1.5k from Dering Harbor center

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

4 Bedrooms10 Guests
9.0

Fabulous

41 reviews

$814
Average price / night
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NF Wine Country Retreat with Dock
NF Wine Country Retreat with Dock
House
Southold, NY, USA
9.4k from Dering Harbor center

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

1 Bedroom8 Guests
New to Booking
$499
Average price / night
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Classic Waterview Victorian Summer Cottage in Park-Like-Setting
Classic Waterview Victorian Summer Cottage in Park-Like-Setting
House
Shelter Island Heights, NY, 11965, United States
1.5k from Dering Harbor center

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

5 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$688
Average price / night
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Very Large, Comfortable, Victorian 4 Bedroom House + Beach Club
Very Large, Comfortable, Victorian 4 Bedroom House + Beach Club
House
Shelter Island Heights, NY, 11965, United States
1.6k from Dering Harbor center

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

4 Bedrooms6 Guests
9.6

Exceptional

7 reviews

$1001
Average price / night
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Peaceful and Private Shelter Island Getaway
Peaceful and Private Shelter Island Getaway
House
Shelter Island, NY, 11964, United States
1.7k from Dering Harbor center

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

3 Bedrooms5 Guests
10.0

Exceptional

52 reviews

$402
Average price / night
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Greenport Gem: Private Saltwater Pool, Awesome Basement, Walk to Everything!
Greenport Gem: Private Saltwater Pool, Awesome Basement, Walk to Everything!
House
Greenport, NY, 11944, United States
1.9k from Dering Harbor center

AC, Barbecue, Crib, Dryer, Extra Bed, Fireplace, Fitness Equipment, Free Parking, Heater

3 Bedrooms8 Guests
9.8

Exceptional

12 reviews

$1119
Average price / night
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Exquisite Waterfront Townhome in Greenport with Pool and Boat Slip. Walk to all!
Exquisite Waterfront Townhome in Greenport with Pool and Boat Slip. Walk to all!
House
Greenport, NY, 11944, United States
1.9k from Dering Harbor center

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

2 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$698
Average price / night
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The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town
The Greenport Beach Cottage: 3 Min Walk to Beach, 1 mile to Town
Cottage
Greenport, NY, 11944, United States
2.0k from Dering Harbor center

AC, Barbecue, Crib, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave

2 Bedrooms5 Guests
10.0

Exceptional

1 reviews

$738
Average price / night
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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
2.0k from Dering Harbor center

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

3 Bedrooms6 Guests
9.8

Exceptional

43 reviews

$318
Average price / night
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Private & Spacious Five Room Suite..Steps To Bay Beach and walk to Village.
Private & Spacious Five Room Suite..Steps To Bay Beach and walk to Village.
Apartment
Greenport, NY, 11944, United States
2.0k from Dering Harbor center

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

2 Bedrooms4 Guests
10.0

Exceptional

150 reviews

$518
Average price / night
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Relax By The Pool, Or Walk To The Beach And Restaurants
Relax By The Pool, Or Walk To The Beach And Restaurants
House
Shelter Island Heights, NY, 11965, United States
2.0k from Dering Harbor center

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

3 Bedrooms6 Guests
10.0

Exceptional

4 reviews

$710
Average price / night
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Elegant Victorian in the Heart of Greenport
Elegant Victorian in the Heart of Greenport
House
Greenport, NY, 11944, United States
2.0k from Dering Harbor center

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

4 Bedrooms13 Guests
New to Booking
$1147
Average price / night
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5 minute walk to beaches and beautiful downtown Greenport
5 minute walk to beaches and beautiful downtown Greenport
House
Greenport, NY, 11944, United States
2.0k from Dering Harbor center

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

1 Bedroom4 Guests
10.0

Exceptional

6 reviews

$308
Average price / night
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Sterling Harbor, walking distance to the center: spacious studio for 4 people
Sterling Harbor, walking distance to the center: spacious studio for 4 people
Apartment
Greenport, NY, 11944, United States
2.1k from Dering Harbor center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Laundry, Living Area, No Smoking

8.0

Good

1 reviews

$365
Average price / night
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The Village Villa – Renovated 6-Bedroom Home in the Heart of Greenport Village
The Village Villa – Renovated 6-Bedroom Home in the Heart of Greenport Village
House
Greenport, NY, 11944, United States
2.1k from Dering Harbor center

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

6 Bedrooms13 Guests
10.0

Exceptional

2 reviews

$902
Average price / night
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Quiet street one block to shops, restaurants & waterfront. Barn with AC TV &WIFI
Quiet street one block to shops, restaurants & waterfront. Barn with AC TV &WIFI
House
Greenport, NY, 11944, United States
2.1k from Dering Harbor center

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

3 Bedrooms6 Guests
10.0

Exceptional

53 reviews

$614
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 Oceanfront Rentals in Dering Harbor.

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Frequently Asked Questions

You can explore 158 verified oceanfront rentals in Dering Harbor. These properties are located directly along the shoreline, offering uninterrupted access to the beach and ocean views.

Oceanfront rental prices in Dering Harbor 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 Dering Harbor 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 Dering Harbor welcome pets. Currently, 26 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 Dering Harbor 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.