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

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  3.  USA

  4.  New York

  5.  Southold
  6.  The Old Field Vineyards

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43 Beach Home Rentals in The Old Field Vineyards (Starting from $280)

Updated Historic shingle-style 1902 4-bedroom Beach House on Southold Bay!
Updated Historic shingle-style 1902 4-bedroom Beach House on Southold Bay!
House
Southold, NY, 11971, United States
0.3k from The Old Field Vineyards center

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

4 Bedrooms8 Guests
10.0

Exceptional

3 reviews

$710
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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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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Nautical Peconic Bayfront Home - Walk to Town
Nautical Peconic Bayfront Home - Walk to Town
House
Southold, NY, 11971, United States
0.5k from The Old Field Vineyards center

AC, Balcony, Dryer, Fitness Equipment, Heater, Hot Tub, Internet, Laundry, No Smoking

4 Bedrooms8 Guests
New to Booking
$698
Average price / night
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Stylish beach getaway: pool in prime location
Stylish beach getaway: pool in prime location
House
Southold, NY, 11971, United States
0.9k from The Old Field Vineyards center

AC, Dryer, Heater, Internet, Kitchen, Laundry, Living Area, No Smoking, Outdoor Space

3 Bedrooms6 Guests
New to Booking
$979
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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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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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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Waterfront, private beach, ready for adventure, light & bright!
Waterfront, private beach, ready for adventure, light & bright!
House
Southold, NY, 11971, United States
1.0k from The Old Field Vineyards center

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

4 Bedrooms10 Guests
10.0

Exceptional

19 reviews

$698
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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Lovely 4 Bedroom Southold Home Walking Distance to Peconic Bay
Lovely 4 Bedroom Southold Home Walking Distance to Peconic Bay
House
Southold, NY, 11971, United States
1.1k from The Old Field Vineyards center

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

4 Bedrooms6 Guests
10.0

Exceptional

2 reviews

$398
Average price / night
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North Beach Fork Beach House
North Beach Fork Beach House
House
Southold, NY, 11971, United States
1.2k from The Old Field Vineyards center

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

3 Bedrooms6 Guests
9.6

Exceptional

39 reviews

$399
Average price / night
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Sweet Southold Beach Cottage FALL WINTER SPRING SUMMER 1 min walk to beach
Sweet Southold Beach Cottage FALL WINTER SPRING SUMMER 1 min walk to beach
House
Southold, NY, 11971, United States
1.2k from The Old Field Vineyards center

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

2 Bedrooms2 Guests
7.0

Good

2 reviews

$280
Average price / night
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Cozy studio with WiFi and AC in welcoming Southold
Cozy studio with WiFi and AC in welcoming Southold
Apartment
Southold, NY, 11971, United States
1.3k from The Old Field Vineyards center

AC, Free Parking, Heater, Internet, Kitchen, No Smoking, Patio

1 Bedroom3 Guests
9.2

Superb

7 reviews

$284
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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Farmhouse Retreat
Farmhouse Retreat
House
Southold, NY, 11971, United States
1.5k from The Old Field Vineyards center

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

2 Bedrooms4 Guests
New to Booking
$780
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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Lovely, Serene and Stylish Country Cottage
Lovely, Serene and Stylish Country Cottage
House
Southold, NY, 11971, United States
1.7k from The Old Field Vineyards center

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

3 Bedrooms4 Guests
9.6

Exceptional

4 reviews

$450
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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House of Classic Arts and Crafts North Fork
House of Classic Arts and Crafts North Fork
House
Southold, NY, 11971, United States
2.4k from The Old Field Vineyards center

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

3 Bedrooms6 Guests
9.8

Exceptional

17 reviews

$455
Average price / night
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Bayfront Vacation Home in Southold, 5 Bedrooms
Bayfront Vacation Home in Southold, 5 Bedrooms
House
Southold, NY, 11971, United States
2.4k from The Old Field Vineyards center

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

5 Bedrooms8 Guests
10.0

Exceptional

9 reviews

$839
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
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 Beach Rentals in The Old Field Vineyards.

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

The Old Field Vineyards Beach Rentals on the Map

Frequently Asked Questions

You can explore 43 verified beach rentals in The Old Field Vineyards. 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 The Old Field Vineyards vary depending on the season, property size, and distance from the shoreline. Rates typically start from around $280 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 The Old Field Vineyards 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 The Old Field Vineyards welcome pets. Currently, 24 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 The Old Field Vineyards 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.