Top Winter Vacations - Vacation Rentals in Little Bay

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From US $1,288

         

9.6 (5 Reviews)

House

Orient Point Vacation Home Saltwater Pool and Five Bedrooms Book Summer Now

• Air Conditioner
• Parking
• Pool

• New York
• Orient

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From US $306

         

New

Villa

BayFront Cottage

• Air Conditioner
• Parking
• View

• New York
• Orient

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From US $827

         

9.8 (61 Reviews)

House

Beachfront vacation Dream house in Long Island Sound.

• Air Conditioner
• Parking
• Pet Friendly

• New York
• Orient

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From US $581

         

9.8 (20 Reviews)

House

The Lane House | Private Beach Escape

• Air Conditioner
• Parking
• Pet Friendly

• Orient
• Orient Point

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From US $1,689

         

9.4 (10 Reviews)

House

Beachfront Heated Pool Hot Tub Orient Village Modern Dream Home

• Air Conditioner
• Parking
• Pet Friendly

• New York
• Orient

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From US $535

         

9.4 (6 Reviews)

House

Orient Point Cottage with Private Beach

• Air Conditioner
• Pool
• TV

• Orient
• Orient Point

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From US $1,910

         

New

House

Private Vineyard Estate in Orient Village w Pool/AC/Walk to Beach & Town

• Air Conditioner
• Parking
• Pet Friendly

• New York
• Orient

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From US $1,906

         

New

House

Poolside Orient Pt by the sea

• Air Conditioner
• Parking
• Pool

• Orient
• Orient Point

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From US $847

         

9.6 (60 Reviews)

House

Orient Point Waterfront Home – Private Beach & Stunning Views

• Air Conditioner
• Parking
• Pool

• Orient
• Orient Point

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From US $1,157

         

9.6 (21 Reviews)

House

Orient Point Family Waterfront Home

• Air Conditioner
• Parking
• TV

• New York
• Town of Southold Town

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From US $560

         

10.0 (98 Reviews)

House

Charming Country Home sits on a 3-acre property in Bucolic Orient.

• Air Conditioner
• Parking
• Pet Friendly

• New York
• Orient

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From US $971

         

10.0 (21 Reviews)

House

Magnificent Private Orient Beach Front House

• Air Conditioner
• Parking
• TV

• Orient
• Orient Point

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From US $1,159

         

10.0 (4 Reviews)

Villa

1.5 Acre Luxury Escape - Saltwater Pool with Water Views

• Air Conditioner
• Parking
• Pet Friendly

• Orient
• Orient Point

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From US $1,285

         

10.0 (1 Review)

House

Gorgeous North Fork Farmhouse with Private Beach Rights

• Air Conditioner
• Parking
• TV

• Orient
• Orient Point

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From US $1,150

         

10.0 (1 Review)

House

Luxurious Brand New Home Steps from Beach, Pool and Family-Friendly Amenities!

• Air Conditioner
• Pool
• TV

• Orient
• Orient Point

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From US $885

         

New

House

Preview listing: One-of-a-kind historic home in Orient with space to spread out

• Air Conditioner
• Parking
• TV

• New York
• Orient

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From US $711

         

New

House

Serene East End Oasis

• Air Conditioner
• Parking
• Pool

• Orient
• Orient Point

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From US $1,766

         

10.0 (8 Reviews)

Other

Cozy Orient Farmhouse on 1.6 Acres with Pool and Walk to Beach

• Air Conditioner
• Parking
• Pool

• Orient
• Orient Point

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From US $1,753

         

10.0 (5 Reviews)

Other

Private Beach and Ing Pool! New build 4 bed 4.5 bth Farmhouse! Chefs kitchen

• Air Conditioner
• Parking
• Pool

• Orient
• Orient Point

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From US $1,282

         

10.0 (4 Reviews)

House

Luxury home with outdoor heated pool, beach access. n Rental permit #0441

• Air Conditioner
• Parking
• Pet Friendly

• New York
• Orient

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From US $545

         

9.8 (20 Reviews)

House

The Lane House | North Fork Private Beach Escape

• Air Conditioner
• Parking
• Pet Friendly

• Orient
• Orient Point

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From US $1,064

         

8.0 (1 Review)

House

Sunny home near private community beach with private pool, pool spa, backyard

• Air Conditioner
• Parking
• Pool

• Orient
• Orient Point

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From US $1,755

         

New

House

North Fork Entertainer's Delight!

• Air Conditioner
• Parking
• Pet Friendly

• New York
• Orient

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From US $768

         

New

House

Serene East End Oasis

• Air Conditioner
• Parking
• Pool

• Orient
• Orient Point

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★ Pro Tip: Topwintervacations makes it easy to compare the best listings on Topwintervacations homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Topwintervacations 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 Little Bay.