Trips to The Old Field Vineyards

Plan Your Next Trip to The Old Field Vineyards and explore unforgettable sights, local flavors, and exciting experiences.

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From $460

         

9.8 (100 Reviews)

Cottage

'The Gate House'on Beach front Estate with Dockage. Walk to Village .

• Air Conditioner
• Parking
• Pet Friendly

• Greenport
• Pipes Cove

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From $438

         

|

New

House

Happiness Comes in Waves

• Air Conditioner
• Parking
• Pet Friendly

• New York
• Southold

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From $127

         

10.0 (1 Review)

Cottage

40 m² Cabin ∙ 2 bedrooms ∙ 3 guests

• 430 ft² Cottage
• Parking
• View
• Ocean View

• New York
• Town of Southold Town

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From $315

         

9.4 (72 Reviews)

House

House on Chase Creek

• Air Conditioner
• Parking
• Balcony/Terrace

• Shelter Island Heights
• The Heights

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From $272

         

10.0 (71 Reviews)

Cottage

Cottage on Beach front Estate with Dockage .Walk to Village

• Air Conditioner
• Parking
• Pet Friendly

• Greenport
• Pipes Cove

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From $389

         

10.0 (1 Review)

House

Private Waterfront home Dock Kayak walk to Southold, near Greenp

• Parking
• Child Friendly

• New York
• Southold

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From $321

         

10.0

House

158 m² House ∙ 3 bedrooms ∙ 10 guests

• 1699 ft² House
• Air Conditioner
• Parking
• Pool

• Greenport
• Greenport West

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From $330

         

|

9.2 (11 Reviews)

Bed & Breakfast

Harbor Knoll Bed & Breakfast

• Parking
• Pool
• Private Pool

• Greenport
• Pipes Cove

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From $283

         

8.4 (11 Reviews)

House

Lake House Located Near North Fork Wineries

• Air Conditioner
• Parking
• Pet Friendly

• New York
• Southold

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From $391

         

|

10.0 (1 Review)

House

Bright Oasis in Beautiful North Fork Wine Country

• Air Conditioner
• Parking
• Pet Friendly

• New York
• Southold

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From $158

         

10.0

House

112 m² House ∙ 2 bedrooms ∙ 4 guests

• 1200 ft² House
• Air Conditioner
• Parking
• TV

• New York
• Southold

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From $358

         

|

8.0 (37 Reviews)

Bed & Breakfast

West Neck Guesthouse

• Air Conditioner
• Parking
• Pool

• New York
• Shelter Island Heights

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From $1,154

         

10.0 (181 Reviews)

House

Southold Waterfront with Boat Dock, Boat Ramp, Hot Tub & Beaches

• Air Conditioner
• Parking
• TV

• New York
• Southold

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From $233

         

|

10.0 (1 Review)

House

Classic Southold Country Charmer

• View
• Wheelchair Accessible
• Balcony/Terrace

• New York
• Southold

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From $505

         

10.0 (150 Reviews)

Apartment

Private & Spacious Five Room Suite.Steps To Bay Beach and walk to Village.

• Air Conditioner
• Parking
• TV

• Greenport
• Pipes Cove

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From $341

         

|

9.8 (71 Reviews)

Bed & Breakfast

Seven Resort Style Inn near Beach

• Air Conditioner
• Parking
• Pet Friendly

• New York
• Shelter Island Heights

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From $485

         

10.0 (81 Reviews)

Condo

Waterfront Condo C204 At The Cliffside Resort With Amazing Water & Sunset Views

• Air Conditioner
• Parking
• Pool

• Greenport
• Greenport West

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From $345

         

|

9.2 (40 Reviews)

Bed & Breakfast

A Walk in the Woods Bed and Breakfast

• Air Conditioner
• Parking
• Balcony/Terrace

• New York
• Southold

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From $342

         

10.0 (66 Reviews)

Cottage

Southold cottage with Private Beach Rights ~ Walk to Kayak & Paddle Board

• Air Conditioner
• Parking
• Pet Friendly

• New York
• Southold

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From $375

         

|

9.0 (23 Reviews)

Bed & Breakfast

Harbor Knoll Bed and Breakfast

• Air Conditioner
• Parking
• Pool

• Greenport
• Pipes Cove

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From $939

         

10.0 (30 Reviews)

House

Tranquility Base; Architect-Renovated, Modern Ranch With Heated Pool

• Air Conditioner
• Parking
• Pet Friendly

• New York
• Shelter Island

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From $689

         

|

9.0 (4 Reviews)

Bed & Breakfast

Vine & Sand-Southold NY's Newest B&B

• Air Conditioner
• Parking
• Pool

• New York
• Town of Southold Town

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From $514

         

10.0 (26 Reviews)

House

I’ve had the best guests!

• Air Conditioner
• Parking
• Pool

• New York
• Southold

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From $757

         

10.0 (24 Reviews)

House

Southold Soundfront Private Beach

• Air Conditioner
• View
• Ocean View

• New York
• Southold

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★ Pro Tip: Smartours makes it easy to compare the best listings on Smartours homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Smartours homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in The Old Field Vineyards.