Holiday Rentals in Port Jefferson, NY

26 available vacation rental offers

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Port Jefferson, NY holiday rentals
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26 Holiday rentals and Airbnb in Port Jefferson, NY

Beachfront Estate, Private Beach & Heated Pool - Port Jefferson, NY
9.7 37 reviews

Beachfront Estate, Private Beach & Heated Pool

apartment, East Shoreham
This luxurious beachfront estate is located in East Shoreham, on Long Island's secluded North Fork, a short drive (approximately 48km) from the Hamptons and Splish Splash Water Park.
Sleeping up to 14 guests in six bedrooms, three bathrooms, and boasting a private pool, extensive deck, and fully equipped kitchen, this manor house offers year-round activities including access to local shops, wineries, and seasonal attractions such as pumpkin picking and berry picking.
The Osprey - Luxury Waterfront Estate - Port Jefferson, NY
No reviews

The Osprey - Luxury Waterfront Estate

apartment, Belle Terre
This Port Jefferson holiday let offers an 11-bedroom, 14-bathroom apartment accommodating up to 32 guests, situated just 730 metres on foot from White Beach and a short 4-minute drive from Harborfront Park, Port Jefferson village, and the Mather House Museum, providing convenient access to local attractions and natural beauty including Avalon Park and Preserve and Brookhaven State Park.
Guests can enjoy the convenience of on-site laundry facilities and explore nearby family-friendly spots such as the Maritime Explorium, with a check-out time of 11:00.
Elegant 6br W/ 3 Master Suites - Port Jefferson, NY
No reviews

Elegant 6br W/ 3 Master Suites

apartment, Smithtown
This expansive private estate is located at the secluded end of a quiet cul-de-sac in Smithtown, offering a tranquil escape.
This five-bedroom detached house sleeps up to 14 guests and features a chef's kitchen, resort-style swimming pool, hot tub, garden, fitness centre, and parking, ideal for families and groups seeking a luxurious stay.
Beachfront Mansion Private Path To Private Beach - Port Jefferson, NY
9.8 10 reviews

Beachfront Mansion Private Path To Private Beach

apartment, East Shoreham
This beachfront holiday home in Shoreham offers direct access to Long Island Sound via a private sandy path, situated approximately 16-24 kilometres from North Fork towns and 48 kilometres from The Hamptons, with JFK Airport 96 kilometres away.
This expansive 6-bedroom, 4-bathroom property accommodates up to 14 guests with a private swimming pool, deck, grill, separate TV den, and indoor fireplace, while nearby attractions include La Plage restaurant, Splish Splash Water Park (27 kilometres) and Riverhead Outlet Shopping (32 kilometres).

Best family friendly Port Jefferson, NY holiday rentals

Among the 26 accommodations in Port Jefferson, NY, here are the 2 best family friendly rentals

Beachfront Mansion Private Path To Private Beach - Port Jefferson, NY
9.8 10 reviews

Beachfront Mansion Private Path To Private Beach

apartment, East Shoreham
This beachfront holiday home in Shoreham offers direct access to Long Island Sound via a private sandy path, situated approximately 16-24 kilometres from North Fork towns and 48 kilometres from The Hamptons, with JFK Airport 96 kilometres away.
This expansive 6-bedroom, 4-bathroom property accommodates up to 14 guests with a private swimming pool, deck, grill, separate TV den, and indoor fireplace, while nearby attractions include La Plage restaurant, Splish Splash Water Park (27 kilometres) and Riverhead Outlet Shopping (32 kilometres).
Beachfront Estate, Private Beach & Heated Pool - Port Jefferson, NY
9.7 37 reviews

Beachfront Estate, Private Beach & Heated Pool

apartment, East Shoreham
This luxurious beachfront estate is located in East Shoreham, on Long Island's secluded North Fork, a short drive (approximately 48km) from the Hamptons and Splish Splash Water Park.
Sleeping up to 14 guests in six bedrooms, three bathrooms, and boasting a private pool, extensive deck, and fully equipped kitchen, this manor house offers year-round activities including access to local shops, wineries, and seasonal attractions such as pumpkin picking and berry picking.

Best Port Jefferson, NY holiday rentals with parking

Beachfront Mansion Private Path To Private Beach - Port Jefferson, NY
9.8 10 reviews

Beachfront Mansion Private Path To Private Beach

apartment, East Shoreham
This beachfront holiday home in Shoreham offers direct access to Long Island Sound via a private sandy path, situated approximately 16-24 kilometres from North Fork towns and 48 kilometres from The Hamptons, with JFK Airport 96 kilometres away.
This expansive 6-bedroom, 4-bathroom property accommodates up to 14 guests with a private swimming pool, deck, grill, separate TV den, and indoor fireplace, while nearby attractions include La Plage restaurant, Splish Splash Water Park (27 kilometres) and Riverhead Outlet Shopping (32 kilometres).
Elegant 6br W/ 3 Master Suites - Port Jefferson, NY
No reviews

Elegant 6br W/ 3 Master Suites

apartment, Smithtown
This expansive private estate is located at the secluded end of a quiet cul-de-sac in Smithtown, offering a tranquil escape.
This five-bedroom detached house sleeps up to 14 guests and features a chef's kitchen, resort-style swimming pool, hot tub, garden, fitness centre, and parking, ideal for families and groups seeking a luxurious stay.
Beachfront Estate, Private Beach & Heated Pool - Port Jefferson, NY
9.7 37 reviews

Beachfront Estate, Private Beach & Heated Pool

apartment, East Shoreham
This luxurious beachfront estate is located in East Shoreham, on Long Island's secluded North Fork, a short drive (approximately 48km) from the Hamptons and Splish Splash Water Park.
Sleeping up to 14 guests in six bedrooms, three bathrooms, and boasting a private pool, extensive deck, and fully equipped kitchen, this manor house offers year-round activities including access to local shops, wineries, and seasonal attractions such as pumpkin picking and berry picking.

Frequently asked questions about holiday rentals in Port Jefferson, NY

  • What are some interesting places to visit in or near Port Jefferson, NY?

    There are loads of interesting places to visit in Port Jefferson! You can't miss the historic Port Jefferson Village, with its charming shops and restaurants. For a bit of history, head to the Vanderbilt Museum, which has a fantastic collection of natural history exhibits. If you're looking for a scenic walk, the Harborfront Park is a great spot, with stunning views of the Long Island Sound.
  • What are the best Airbnb and holiday rentals in Port Jefferson, NY?

    The Palm Tree 2nd Floor Suite, The Palm Tree Extended Stay and Luxury Suite 5 Minutes From Stony Brook University are among the best Airbnb and holiday rentals in Port Jefferson, NY.

  • Which walking or cycling routes are the best in Port Jefferson, NY?

    Port Jefferson is perfect for a stroll or bike ride. The scenic waterfront walk along the harbour is a classic, with lovely views of the boats and the lighthouse. For a longer ride, you can cycle along the North Shore Bike Path, which stretches along the coast. It's a great way to take in the beautiful scenery.
  • What are the most popular Airbnbs in Port Jefferson, NY?

    Among the Airbnbs in Port Jefferson, NY, The Palm Tree 2nd Floor Suite, The Palm Tree Extended Stay and Luxury Suite 5 Minutes From Stony Brook University are the most popular ones.

  • What sports or outdoor activites can visitors enjoy in and around Port Jefferson, NY?

    Port Jefferson is a great place for outdoor activities. You can go kayaking or paddleboarding in the harbour, or rent a boat and explore the Long Island Sound. In the summer, the beaches are perfect for swimming, sunbathing, and enjoying the warm weather. There's also a lovely park called Hallock State Park Preserve, where you can go hiking and enjoy the natural beauty of Long Island.
  • What are the best holiday rentals with a pool in Port Jefferson, NY?

  • What other towns or cities can be easily accessed from Port Jefferson, NY?

    Port Jefferson is well-connected. You can easily hop on the Long Island Rail Road and head into New York City, which is about an hour away. If you're looking for a charming coastal town nearby, Stony Brook is just a short drive away, and it has a beautiful campus and some lovely restaurants.
  • What are the best rentals for families and kids in Port Jefferson, NY?

  • What amenities are commonly available in vacation rentals in Port Jefferson, NY?

    Most vacation rentals in Port Jefferson are well-equipped. You'll typically find amenities like Wi-Fi, a fully equipped kitchen, and a comfortable living space. Many rentals also have laundry facilities and outdoor space, such as a patio or balcony, which is great for enjoying the fresh air.
  • What are the best rentals or Airbnbs with a jacuzzi in Port Jefferson, NY?

    The best vacation rentals or Airbnb with a jacuzzi in Port Jefferson, NY are 1856 Trading House W\/ Walk To Water, Harborside Serenity and 1856 Trading House Close To Water.

  • What time of year is best to rent a vacation rental Port Jefferson, NY?

    The best time to visit Port Jefferson depends on what you're looking for. Summer is the busiest season, with warm weather and plenty of outdoor activities. Spring and autumn are also lovely times to visit, with mild temperatures and fewer crowds. If you're looking for a quieter experience, winter can be a good option, as it offers a different kind of charm.

Popular destinations

Best Port Jefferson, NY holiday rentals with a balcony

Beachfront Mansion Private Path To Private Beach - Port Jefferson, NY
9.8 10 reviews

Beachfront Mansion Private Path To Private Beach

apartment, East Shoreham
This beachfront holiday home in Shoreham offers direct access to Long Island Sound via a private sandy path, situated approximately 16-24 kilometres from North Fork towns and 48 kilometres from The Hamptons, with JFK Airport 96 kilometres away.
This expansive 6-bedroom, 4-bathroom property accommodates up to 14 guests with a private swimming pool, deck, grill, separate TV den, and indoor fireplace, while nearby attractions include La Plage restaurant, Splish Splash Water Park (27 kilometres) and Riverhead Outlet Shopping (32 kilometres).

Best Port Jefferson, NY holiday rentals with air conditioning

Elegant 6br W/ 3 Master Suites - Port Jefferson, NY
No reviews

Elegant 6br W/ 3 Master Suites

apartment, Smithtown
This expansive private estate is located at the secluded end of a quiet cul-de-sac in Smithtown, offering a tranquil escape.
This five-bedroom detached house sleeps up to 14 guests and features a chef's kitchen, resort-style swimming pool, hot tub, garden, fitness centre, and parking, ideal for families and groups seeking a luxurious stay.
Beachfront Mansion Private Path To Private Beach - Port Jefferson, NY
9.8 10 reviews

Beachfront Mansion Private Path To Private Beach

apartment, East Shoreham
This beachfront holiday home in Shoreham offers direct access to Long Island Sound via a private sandy path, situated approximately 16-24 kilometres from North Fork towns and 48 kilometres from The Hamptons, with JFK Airport 96 kilometres away.
This expansive 6-bedroom, 4-bathroom property accommodates up to 14 guests with a private swimming pool, deck, grill, separate TV den, and indoor fireplace, while nearby attractions include La Plage restaurant, Splish Splash Water Park (27 kilometres) and Riverhead Outlet Shopping (32 kilometres).
Beachfront Estate, Private Beach & Heated Pool - Port Jefferson, NY
9.7 37 reviews

Beachfront Estate, Private Beach & Heated Pool

apartment, East Shoreham
This luxurious beachfront estate is located in East Shoreham, on Long Island's secluded North Fork, a short drive (approximately 48km) from the Hamptons and Splish Splash Water Park.
Sleeping up to 14 guests in six bedrooms, three bathrooms, and boasting a private pool, extensive deck, and fully equipped kitchen, this manor house offers year-round activities including access to local shops, wineries, and seasonal attractions such as pumpkin picking and berry picking.
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