Oceanfront Rentals in The Old Field Vineyards, NY: Compare 10+ Sites & Save

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  2. Oceanfront Rentals
  3.  USA

  4.  New York

  5.  Southold
  6.  The Old Field Vineyards

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170 Best Oceanfront Rentals in The Old Field Vineyards (Starting from $236)

The Cliffside Resort Condominiums
The Cliffside Resort Condominiums
Apartment
Greenport, NY, USA
3.5k from The Old Field Vineyards 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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Sandy Bay Beach
Sandy Bay Beach
House
Southold, NY, 11971, United States
0.3k from The Old Field Vineyards center

AC, Fireplace, Internet, Kitchen, Living Area, Microwave, No Smoking, TV

3 Bedrooms7 Guests
8.0

Good

2 reviews

$1249
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
3.6k from The Old Field Vineyards 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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5 Bedrooms ~ Steps from a Private Sandy Beach and Beautiful Vineyard Views..
5 Bedrooms ~ Steps from a Private Sandy Beach and Beautiful Vineyard Views..
House
Southold, NY, 11971, United States
0.4k from The Old Field Vineyards center

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

5 Bedrooms10 Guests
9.8

Exceptional

6 reviews

$1652
Average price / night
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NF Wine Country Retreat with Dock
NF Wine Country Retreat with Dock
House
Southold, NY, USA
3.7k from The Old Field Vineyards 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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Unique Southold waterfront luxury home with heated pool on Long Creek
Unique Southold waterfront luxury home with heated pool on Long Creek
House
Southold, NY, 11971, United States
0.9k from The Old Field Vineyards center

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

4 Bedrooms10 Guests
9.6

Exceptional

18 reviews

$851
Average price / night
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Watersedge Retreat
Watersedge Retreat
House
Southold, NY, USA
4.5k from The Old Field Vineyards 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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Charming Southold Retreat with In Ground Pool – Walk to Founder’s Beach
Charming Southold Retreat with In Ground Pool – Walk to Founder’s Beach
House
Southold, NY, 11971, United States
1.0k from The Old Field Vineyards center

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

3 Bedrooms6 Guests
New to Booking
$354
Average price / night
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Bright Apartment - half Mi to Greenport Harbor!
Bright Apartment - half Mi to Greenport Harbor!
Apartment
Greenport, NY, USA
5.7k from The Old Field Vineyards 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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Privacy!! Heated salt-water pool, central a/c, all kinds of families welcome
Privacy!! Heated salt-water pool, central a/c, all kinds of families welcome
House
Southold, NY, 11971, United States
1.0k from The Old Field Vineyards center

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

3 Bedrooms8 Guests
9.0

Fabulous

2 reviews

$923
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
8.0k from The Old Field Vineyards 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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Southold Escape with Large Saltwater Pool on Wine Trail
Southold Escape with Large Saltwater Pool on Wine Trail
House
Southold, NY, 11971, United States
1.0k from The Old Field Vineyards center

AC, Barbecue, Dryer, Fitness Equipment, Heater, Internet, Kitchen, Laundry, Microwave

3 Bedrooms6 Guests
9.6

Exceptional

10 reviews

$973
Average price / night
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Villa Ebrar - Luxury with pool
Villa Ebrar - Luxury with pool
Villa
Sag Harbor, NY, USA
9.8k from The Old Field Vineyards center

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

4 Bedrooms8 Guests
New to Booking
$500
Average price / night
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North Fork 7 Bedroom Farmhouse Escape
North Fork 7 Bedroom Farmhouse Escape
House
Southold, NY, 11971, United States
1.4k from The Old Field Vineyards center

AC, Arcade, Barbecue, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen

7 Bedrooms10 Guests
9.6

Exceptional

5 reviews

$898
Average price / night
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Beautiful waterfront house in Southold
Beautiful waterfront house in Southold
House
Southold, NY, 11971, United States
1.4k from The Old Field Vineyards center

AC, Dryer, Extra Bed, Internet, Laundry, No Smoking, Washer

4 Bedrooms9 Guests
10.0

Exceptional

1 reviews

$1107
Average price / night
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Charming Cottage
Charming Cottage
Cottage
Southold, NY, 11971, United States
1.5k from The Old Field Vineyards center

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

2 Bedrooms4 Guests
10.0

Exceptional

34 reviews

$474
Average price / night
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Renovated American Farmhouse in the heart of Southold with heated saltwater pool
Renovated American Farmhouse in the heart of Southold with heated saltwater pool
House
Southold, NY, 11971, United States
1.7k from The Old Field Vineyards center

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

4 Bedrooms8 Guests
10.0

Exceptional

29 reviews

$1241
Average price / night
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Shelter Bay Cove Waterfront + Beach + spectacular
Shelter Bay Cove Waterfront + Beach + spectacular
House
Southold, NY, 11971, United States
1.8k from The Old Field Vineyards center

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

3 Bedrooms7 Guests
10.0

Exceptional

6 reviews

$637
Average price / night
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Sunset Perch: Heated Pool, Rooftop Deck, Walk to Beach
Sunset Perch: Heated Pool, Rooftop Deck, Walk to Beach
House
North Fork, NY, 11971, United States
1.9k from The Old Field Vineyards center

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

5 Bedrooms10 Guests
New to Booking
$1784
Average price / night
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Shorecrest Beach House + Beach Front + Ocean views
Shorecrest Beach House + Beach Front + Ocean views
House
Southold, NY, 11971, United States
2.0k from The Old Field Vineyards center

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

4 Bedrooms10 Guests
9.8

Exceptional

28 reviews

$944
Average price / night
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Greenport Getaway the perfect blend of relaxation, nature, and North Fork charm.
Greenport Getaway the perfect blend of relaxation, nature, and North Fork charm.
House
Greenport, NY, 11944, United States
2.3k from The Old Field Vineyards center

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

5 Bedrooms10 Guests
9.8

Exceptional

79 reviews

$939
Average price / night
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NorthFork Serenity, next to beach and wineries
NorthFork Serenity, next to beach and wineries
House
Southold, NY, 11971, United States
2.4k from The Old Field Vineyards center

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

3 Bedrooms8 Guests
10.0

Exceptional

2 reviews

$642
Average price / night
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One block from the beach!!
One block from the beach!!
House
Southold, NY, 11971, United States
2.4k from The Old Field Vineyards center

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

3 Bedrooms8 Guests
New to Booking
$1087
Average price / night
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Panoramic Water Views, Plunge Pool, Hot Tub, Fire Pit & Walk to Beach
Panoramic Water Views, Plunge Pool, Hot Tub, Fire Pit & Walk to Beach
House
Southold, NY, 11971, United States
2.4k from The Old Field Vineyards center

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

4 Bedrooms11 Guests
10.0

Exceptional

15 reviews

$2456
Average price / night
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Southold 3BR Waterfront Home | Dock, Kayaks, Creek Views
Southold 3BR Waterfront Home | Dock, Kayaks, Creek Views
House
Southold, NY, 11971, United States
2.5k from The Old Field Vineyards center

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

3 Bedrooms6 Guests
9.4

Superb

21 reviews

$639
Average price / night
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Spacious North Fork Home in Greenport, Heated Pool, Perfect for Families
Spacious North Fork Home in Greenport, Heated Pool, Perfect for Families
House
Greenport, NY, 11944, United States
2.6k from The Old Field Vineyards center

AC, Barbecue, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater, Hot Tub, Kitchen

4 Bedrooms8 Guests
10.0

Exceptional

4 reviews

$1559
Average price / night
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Historic 2-bedroom upstairs apartment close to beaches, town and vineyards.
Historic 2-bedroom upstairs apartment close to beaches, town and vineyards.
House
Southold, NY, 11971, United States
2.6k from The Old Field Vineyards center

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

2 Bedrooms4 Guests
9.4

Superb

14 reviews

$447
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 The Old Field Vineyards.

Where to stay in The Old Field Vineyards? Best neighborhoods & areas

The Old Field Vineyards Oceanfront Rentals on the Map

Frequently Asked Questions

You can explore 170 verified oceanfront rentals in The Old Field Vineyards. These properties are located directly along the shoreline, offering uninterrupted access to the beach and ocean views.

Oceanfront rental prices in The Old Field Vineyards 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 The Old Field Vineyards 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 The Old Field Vineyards 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 The Old Field Vineyards often include features designed for a comfortable coastal stay, such as View, Oceanfront, and Ocean 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.