Trips to Osprey's Dominion

Plan Your Next Trip to Osprey's Dominion and explore unforgettable sights, local flavors, and exciting experiences.

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From $937

         

10.0 (33 Reviews)

House

Gorgeous Historical 6 bdrm House close to vineyards and breweries,

• Air Conditioner
• Parking
• TV

• New York
• Peconic

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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 $273

         

10.0 (5 Reviews)

House

167 m² House ∙ 3 bedrooms ∙ 6 guests

• 1797 ft² House
• Air Conditioner
• Parking
• TV

• New York
• Cutchogue

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From $874

         

10.0 (39 Reviews)

House

Family and dog-friendly getaway near amazing wineries, beaches and restaurants!

• Air Conditioner
• Parking
• Pet Friendly

• New York
• Southold

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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 $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 $264

         

10.0 (3 Reviews)

House

167 m² House ∙ 3 bedrooms ∙ 7 guests

• 1797 ft² House
• Air Conditioner
• Parking
• TV

• New York
• Cutchogue

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From $628

         

9.8 (52 Reviews)

House

Charming Country Home, Minutes to Sandy beaches, in the Heart of Wine Country

• Air Conditioner
• Parking
• TV

• New York
• Cutchogue

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From $467

         

10.0 (182 Reviews)

Cottage

Fabulous Waterfront Property in the Heart of Wine Country

• Air Conditioner
• Parking
• TV

• New York
• Peconic

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From $984

         

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10.0 (1 Review)

House

Peconic Sound Beach Home: Backyard & Vineyards

• Air Conditioner
• Parking
• Pet Friendly

• New York
• Peconic

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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 $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 $391

         

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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 $397

         

10.0 (28 Reviews)

House

North Fork Beach House - short walk to Peconic Bay and beach

• Air Conditioner
• Parking
• TV

• New York
• Cutchogue

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From $252

         

|

10.0 (1 Review)

House

The Endless Summer Cottage

• Air Conditioner
• Security/Safety
• Sports/Activities

• New York
• Cutchogue

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From $393

         

10.0 (27 Reviews)

Cottage

Totally Renovated Cottage on the North Fork 7 min. walk to the Beach

• Air Conditioner
• Parking
• TV

• New York
• Cutchogue

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From $233

         

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10.0 (1 Review)

House

Classic Southold Country Charmer

• View
• Wheelchair Accessible
• Balcony/Terrace

• New York
• Southold

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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 $345

         

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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 $757

         

10.0 (24 Reviews)

House

Southold Soundfront Private Beach

• Air Conditioner
• View
• Ocean View

• New York
• Southold

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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 $922

         

10.0 (13 Reviews)

Apartment

Peconic Bay Beach House + 5 bedrooms + spacious +

• Air Conditioner
• Parking
• TV

• New York
• Southold

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From $425

         

10.0 (11 Reviews)

House

Southold, NY- Heart of North Fork Wine Country and Minutes From The Beach

• Air Conditioner
• Parking
• TV

• New York
• Southold

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From $636

         

10.0 (10 Reviews)

House

Luxury by the Sea

• Air Conditioner
• Parking
• TV

• 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 Osprey's Dominion.