Hotels in Southold, NY

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Southold, NY hotels
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18 Cheap hotels in Southold, NY

Best Southold, NY luxury hotels (4 and 5 stars)

Among the 18 accommodations in Southold, NY, here are the 4 best luxury hotels

The Chequit - Southold, NY
10 1 review

The Chequit

hotel, Shelter Island Heights
The Chequit is located in Shelter Island Heights, a short drive from both Montauk and East Hampton, making it a great base for exploring the beautiful Long Island coastline. This 4-star hotel receives very good user ratings, with guests praising its cleanliness and excellent location.
The hotel has a range of amenities to enjoy, including a restaurant, bar, and sun terrace with sea views. Each room features private bathrooms, air conditioning, and free Wi-Fi, ensuring a comfortable stay.
The Pridwin Hotel - Southold, NY
9.2 230 reviews

The Pridwin Hotel

hotel, Shelter Island Heights
The Pridwin Hotel is situated on Shelter Island, a short ferry ride from the mainland and a short drive from the quaint village of Shelter Island Heights. It is a 4-star hotel with excellent user ratings for location, cleanliness, and overall experience.
The hotel offers a variety of rooms and cottages, all with stunning water views. Guests can enjoy a range of amenities including a swimming pool, spa, restaurant, bar, fitness centre, tennis court, and a variety of seasonal activities.
American Beech Hotel - Southold, NY
9.1 519 reviews

American Beech Hotel

hotel, Greenport
The American Beech Hotel is situated in Greenport, just 26 miles from Splish Splash water park and 48 miles from Long Island MacArthur Airport, making it a convenient base for exploring the charming town and surrounding area. This 4-star hotel has received very good user ratings, indicating a high level of satisfaction among guests.
The hotel offers spacious rooms with air conditioning, seating areas, flat-screen TVs, safety deposit boxes, and private bathrooms with complimentary toiletries. Guests can enjoy a range of amenities, including a swimming pool, terrace, garden, spa, restaurant, bar, and free bikes to explore the local area.
Shelter Island House - Southold, NY
8.5 73 reviews

Shelter Island House

hotel, Shelter Island Heights
The Shelter Island House is situated in Shelter Island Heights, a short distance from the village centre and the island's beautiful beaches. This 4-star hotel enjoys very good user ratings, making it a popular choice for travellers.
The hotel has a range of facilities, including a swimming pool, garden, and terrace, perfect for relaxing and enjoying the sunshine. Guests can also enjoy the on-site restaurant, bar, and spa, as well as take advantage of the concierge service, room service, and free Wi-Fi.

Best Southold, NY hotels with a pool

Among the 18 accommodations in Southold, NY, here are the 4 best hotels with a pool

The Pridwin Hotel - Southold, NY
9.2 230 reviews

The Pridwin Hotel

hotel, Shelter Island Heights
The Pridwin Hotel is situated on Shelter Island, a short ferry ride from the mainland and a short drive from the quaint village of Shelter Island Heights. It is a 4-star hotel with excellent user ratings for location, cleanliness, and overall experience.
The hotel offers a variety of rooms and cottages, all with stunning water views. Guests can enjoy a range of amenities including a swimming pool, spa, restaurant, bar, fitness centre, tennis court, and a variety of seasonal activities.
Shelter Island House - Southold, NY
8.5 73 reviews

Shelter Island House

hotel, Shelter Island Heights
The Shelter Island House is situated in Shelter Island Heights, a short distance from the village centre and the island's beautiful beaches. This 4-star hotel enjoys very good user ratings, making it a popular choice for travellers.
The hotel has a range of facilities, including a swimming pool, garden, and terrace, perfect for relaxing and enjoying the sunshine. Guests can also enjoy the on-site restaurant, bar, and spa, as well as take advantage of the concierge service, room service, and free Wi-Fi.
Oyster Estate - Southold, NY
9.1 369 reviews

Oyster Estate

hotel, Greenport
The Greenporter Hotel is situated near the Greenport Village Historic District, a short drive from the East End Seaport Museum and Marina Foundation and a 5-minute walk from the Railroad Museum of Long Island. This 3-star hotel receives very good user ratings for its cleanliness and overall experience.
The Greenporter Hotel offers a unique retro design with modern amenities. Guests can enjoy a weekend continental breakfast, relax by the outdoor pool, and dine at the hotel's new restaurant and cocktail bar, Terra, which also serves coffee daily.
The Harbor Front Inn - Southold, NY
8.8 964 reviews

The Harbor Front Inn

hotel, Greenport
The Harbor Front Inn is conveniently located in the heart of Greenport, just a short walk from the North Ferry Terminal and a 3-minute drive from Kontokosta Winery. This 3-star hotel consistently receives very good user ratings, making it a popular choice for travellers visiting the area.
The inn offers comfortable rooms with modern amenities, including a flat-screen TV, refrigerator, and private bathroom. Guests can enjoy a range of on-site facilities, such as a swimming pool, fitness centre, and free Wi-Fi.

Frequently asked questions about hotels in Southold, NY

  • What are the top landmarks to see in and around Southold, NY?

    Southold is a charming town with a rich history. The iconic Southold Historical Society Museum is a must-visit for anyone interested in the area's past. You can also visit the historic Horton Point Lighthouse, which offers stunning views of the Long Island Sound. For a glimpse into the town's agricultural heritage, take a drive along the scenic Route 25, where you'll find numerous farm stands and vineyards.
  • What are the best hotels with a swimming pool in Southold, NY?

    Sound View Greenport, The Pridwin Hotel and Hotel Moraine are among the best hotels with a swimming pool in Southold, NY.

  • What are the most affordable attractions in and around Southold, NY?

    Southold has plenty of free or low-cost attractions. Take a stroll along the scenic Southold Town Beach, enjoy the beautiful views from the Southold Town Dock, or explore the historic Southold Cemetery, which is a fascinating glimpse into the town's history. For a fun family day out, visit the Southold Farmers Market, which is held every Saturday from May to October.
  • What are the most popular 2, 3 and 4-star hotels in Southold, NY?

    Among 2, 3 and 4-star hotels in Southold, NY, Sound View Greenport, Hotel Moraine and Historic White Blossom House are the most popular ones.

  • How can travelers relax during a week in and arond Southold, NY?

    Southold is the perfect place to unwind and recharge. Spend your mornings kayaking or paddleboarding in the calm waters of the Peconic Bay. In the afternoons, relax on the sandy shores of Southold Town Beach, or take a leisurely bike ride through the scenic countryside. In the evenings, enjoy a delicious meal at one of the many local restaurants, or simply sit on your porch and watch the sunset over the Long Island Sound.
  • What are the best luxury hotels in Southold, NY?

    The Shoals Suites & Slips, The Pridwin Hotel and Sound View Greenport are among the best luxury hotels in Southold, NY.

  • What amenities can travelers expect in hotel rooms in Southold, NY?

    Most hotels in Southold offer standard amenities like air conditioning, comfortable beds, and private bathrooms. Some hotels also have additional features like swimming pools, hot tubs, and fitness centres. If you're looking for a more luxurious experience, there are also a few boutique hotels in the area that offer unique amenities and services.
  • What are the best family friendly hotels in Southold, NY?

    The best family friendly hotels in Southold, NY are Sound View Greenport, The Shoals Suites & Slips and Southold Beach Motel.

  • When is the best time to book a hotel in Southold, NY?

    The best time to book a hotel in Southold is in the shoulder seasons, from April to May and September to October. During these months, the weather is still pleasant, but the crowds are smaller and the prices are more affordable. If you're looking for a more relaxed and affordable experience, avoid booking during the peak summer season, from June to August.
  • What are the best pet friendly hotels in Southold, NY?

    The best pet friendly hotels in Southold, NY are Sound View Greenport, Hotel Moraine and Hotel Moraine.

  • What are some pet-friendly activities in and around Southold, NY?

    Southold is a very dog-friendly town. Many restaurants and shops welcome furry friends, and there are plenty of dog-friendly beaches in the area. For a fun day out with your pet, take a walk along the Southold Town Beach or visit the dog park at the Southold Town Park. You can also explore the scenic trails at the Orient Point State Park, which is a great place for a leisurely walk or run with your dog.
  • What are the best hotels with jacuzzi in Southold, NY?

    Resort Living In Private Beach Community is the best hotel with a jacuzzi in Southold, NY.

  • Which towns or cities worth a visit near Southold, NY?

    A short drive from Southold, you'll find the charming village of Greenport, known for its vibrant waterfront and eclectic shops. For a taste of history, visit the historic town of Sag Harbor, which played a significant role in the whaling industry. If you're looking for a more urban experience, head to the city of Riverhead, which offers a range of shopping, dining, and entertainment options.

Popular destinations

Best Southold, NY hotels with air conditioning

Historic White Blossom House - Southold, NY
9.6 14 reviews

Historic White Blossom House

hotel, Southold
The Historic White Blossom House is a charming inn located in Southold, just a short drive from Cedar Beach Point and Lenz Winery. It is a 2-star property that has received excellent user ratings for its location, cleanliness, and overall experience.
The inn offers a self-catering apartment with a patio and a fully equipped kitchenette, spanning 74 square metres. It features a range of amenities including free Wi-Fi, a garden, a fitness centre, a tennis court, and free parking. Guests can also enjoy free bike hire to explore the surrounding area.
The Pridwin Hotel - Southold, NY
9.2 230 reviews

The Pridwin Hotel

hotel, Shelter Island Heights
The Pridwin Hotel is situated on Shelter Island, a short ferry ride from the mainland and a short drive from the quaint village of Shelter Island Heights. It is a 4-star hotel with excellent user ratings for location, cleanliness, and overall experience.
The hotel offers a variety of rooms and cottages, all with stunning water views. Guests can enjoy a range of amenities including a swimming pool, spa, restaurant, bar, fitness centre, tennis court, and a variety of seasonal activities.
Sound View Greenport - Southold, NY
8.4 974 reviews

Sound View Greenport

hotel, Southold
Sound View Greenport is a 3-star hotel situated on the North Fork in Greenport, just 98 miles from New York City and a short drive from popular destinations like Montauk and East Hampton. It has received very good user ratings, making it a popular choice for travellers seeking a relaxing getaway.
This hotel offers a range of amenities and activities to keep guests entertained, including a seasonal outdoor pool, a private beach area, bike hire, a tennis court, a shared lounge, a bar, and a restaurant. The rooms all have stunning waterfront views, allowing guests to enjoy the beauty of the Long Island Sound.
The Harbor Front Inn - Southold, NY
8.8 964 reviews

The Harbor Front Inn

hotel, Greenport
The Harbor Front Inn is conveniently located in the heart of Greenport, just a short walk from the North Ferry Terminal and a 3-minute drive from Kontokosta Winery. This 3-star hotel consistently receives very good user ratings, making it a popular choice for travellers visiting the area.
The inn offers comfortable rooms with modern amenities, including a flat-screen TV, refrigerator, and private bathroom. Guests can enjoy a range of on-site facilities, such as a swimming pool, fitness centre, and free Wi-Fi.

Best Southold, NY hotels with a balcony

The Pridwin Hotel - Southold, NY
9.2 230 reviews

The Pridwin Hotel

hotel, Shelter Island Heights
The Pridwin Hotel is situated on Shelter Island, a short ferry ride from the mainland and a short drive from the quaint village of Shelter Island Heights. It is a 4-star hotel with excellent user ratings for location, cleanliness, and overall experience.
The hotel offers a variety of rooms and cottages, all with stunning water views. Guests can enjoy a range of amenities including a swimming pool, spa, restaurant, bar, fitness centre, tennis court, and a variety of seasonal activities.
The Harbor Front Inn - Southold, NY
8.8 964 reviews

The Harbor Front Inn

hotel, Greenport
The Harbor Front Inn is conveniently located in the heart of Greenport, just a short walk from the North Ferry Terminal and a 3-minute drive from Kontokosta Winery. This 3-star hotel consistently receives very good user ratings, making it a popular choice for travellers visiting the area.
The inn offers comfortable rooms with modern amenities, including a flat-screen TV, refrigerator, and private bathroom. Guests can enjoy a range of on-site facilities, such as a swimming pool, fitness centre, and free Wi-Fi.
Oyster Estate - Southold, NY
9.1 369 reviews

Oyster Estate

hotel, Greenport
The Greenporter Hotel is situated near the Greenport Village Historic District, a short drive from the East End Seaport Museum and Marina Foundation and a 5-minute walk from the Railroad Museum of Long Island. This 3-star hotel receives very good user ratings for its cleanliness and overall experience.
The Greenporter Hotel offers a unique retro design with modern amenities. Guests can enjoy a weekend continental breakfast, relax by the outdoor pool, and dine at the hotel's new restaurant and cocktail bar, Terra, which also serves coffee daily.
Sound View Greenport - Southold, NY
8.4 974 reviews

Sound View Greenport

hotel, Southold
Sound View Greenport is a 3-star hotel situated on the North Fork in Greenport, just 98 miles from New York City and a short drive from popular destinations like Montauk and East Hampton. It has received very good user ratings, making it a popular choice for travellers seeking a relaxing getaway.
This hotel offers a range of amenities and activities to keep guests entertained, including a seasonal outdoor pool, a private beach area, bike hire, a tennis court, a shared lounge, a bar, and a restaurant. The rooms all have stunning waterfront views, allowing guests to enjoy the beauty of the Long Island Sound.
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