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

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  6.  The Old Field Vineyards

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401 Best Vacation Rentals in The Old Field Vineyards (Starting from $233)

Private Waterfront Home: Dock, Kayaks
Private Waterfront Home: Dock, Kayaks
House
Southold, NY, USA
2.5k from The Old Field Vineyards 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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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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Classic Southold Country Charmer
Classic Southold Country Charmer
House
Southold, NY, USA
2.5k from The Old Field Vineyards 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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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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Private Waterfront home Dock Kayak walk to Southold, near Greenp
Private Waterfront home Dock Kayak walk to Southold, near Greenp
House
The Old Field Vineyards, Southold, New York, USA
2.5k from The Old Field Vineyards center

Parking, Child Friendly

3 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$389
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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Beachfront Greenport Villa
Beachfront Greenport Villa
House
Greenport, NY, USA
2.7k from The Old Field Vineyards center

Air Conditioner, Barbecue/Outdoor Cooking, Parking, Internet, Security/Safety, Child Friendly

3 Bedrooms8 Guests
New to Booking
$913
Average price / night
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Contemporary Colonial home with pristine Peconic bay views, Heated...
Contemporary Colonial home with pristine Peconic bay views, Heated...
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

10 reviews

$2003
Average price / night
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Steve's Place: Heated Pool, 3BR Southold Home, Beach
Steve's Place: Heated Pool, 3BR Southold Home, Beach
House
Southold, NY, USA
3.5k from The Old Field Vineyards center

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

3 Bedrooms6 Guests
New to Booking
$304
Average price / night
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Baylight Haven by Rove Travel | Luxe Home with Bay Views
Baylight Haven by Rove Travel | Luxe Home with Bay Views
House
Southold, NY, 11971, United States
0.5k from The Old Field Vineyards center

AC, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet

4 Bedrooms9 Guests
New to Booking
$1036
Average price / night
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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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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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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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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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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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Waterfront Hot Tub Retreat w Kayaks | Kayak Point
Waterfront Hot Tub Retreat w Kayaks | Kayak Point
House
North Fork, NY, 11971, United States
0.9k from The Old Field Vineyards center

AC, Balcony, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet, Kitchen

4 Bedrooms8 Guests
New to Booking
$858
Average price / night
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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
4.1k from The Old Field Vineyards 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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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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Minnehaha Marvel
Minnehaha Marvel
House
Southold, NY, USA
4.2k from The Old Field Vineyards center

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

1 Bedroom4 Guests
New to Booking
$296
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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Modern on 9th
Modern on 9th
House
Greenport, NY, USA
4.3k from The Old Field Vineyards 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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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
Check Availability
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
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 The Old Field Vineyards.

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

The Old Field Vineyards Vacation Rentals on the Map

Frequently Asked Questions

You can explore 401 verified vacation rentals in The Old Field Vineyards. 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 The Old Field Vineyards 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 The Old Field Vineyards 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 The Old Field Vineyards welcome pets. Currently, 32 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 The Old Field Vineyards often include amenities such as Fireplace/Heating, View, 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.