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.
8.2 315 reviews
Southold, NY
05/07 – 09/07
A$3322/nighttotal: A$13288 (4 )
Sound View Greenport
3 4
hotel , Greenport
Sound View Greenport, a four-star hotel in Greenport, NY, offers a prime location on the coastline with excellent access to local attractions. This family-friendly establishment provides complimentary breakfast, free Wi-Fi, on-site parking, concierge and ticket services, room service, a swimming pool with a poolside bar, and tennis courts, alongside a restaurant and bar.
9.2 522 reviews
Southold, NY
05/07 – 09/07
A$1691/nighttotal: A$6764 (4 )
American Beech Hotel
2 4
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.
8.5 82 reviews
Southold, NY
05/07 – 09/07
A$1897/nighttotal: A$7588 (4 )
Shelter Island House
3 4
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.
9.3 844 reviews
Southold, NY
05/07 – 09/07
A$1134/nighttotal: A$4536 (4 )
Sag Harbor Inn
1 4
hotel , Sag Harbor
The Sag Harbor Inn is located in Sag Harbor, a short distance from Havens Beach and within easy reach of attractions like Montauk Point Lighthouse. The hotel has consistently received excellent ratings for its location, cleanliness, and overall guest experience. The inn offers comfortable rooms with a choice of layouts, including single-bedroom options with a floor area of 36 square metres. Amenities include a seasonal outdoor pool, a shared lounge, free private parking, and a continental breakfast served each morning.
9.4 636 reviews
Southold, NY
05/07 – 09/07
A$1788/nighttotal: A$7152 (4 )
The Shoals Suites & Slips
3 4
hotel , Southold
The Shoals Suites & Slips is located in Southold, a charming village on Long Island's North Fork, just a short drive from the beautiful beaches of Orient Point. It is a 4-star hotel with excellent user ratings. The hotel offers comfortable rooms with private bathrooms and free parking. Guests can enjoy a range of amenities, including a restaurant, bar, terrace, garden, and concierge service.
9.7 195 reviews
Southold, NY
05/07 – 09/07
A$4827/nighttotal: A$19308 (4 )
Hotel Moraine
3 4
hotel , Greenport
Hotel Moraine is located in Greenport, 24 miles from Splish Splash and 46 miles from Long Island MacArthur Airport, making it a convenient base for exploring the area. The hotel consistently receives excellent ratings for its location, cleanliness and overall experience. The hotel offers a range of comfortable rooms, each accommodating up to two guests. Guests can enjoy a variety of amenities, including a seasonal outdoor swimming pool, a fitness centre, a bar and lounge, a sun terrace, free Wi-Fi, and complimentary bikes for exploring the charming streets and waterfront of Greenport.
8.3 942 reviews
Southold, NY
05/07 – 09/07
A$1975/nighttotal: A$7900 (4 )
Sound View Greenport
2 4
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.
9.6 273 reviews
Southold, NY
05/07 – 09/07
A$3213/nighttotal: A$12852 (4 )
The Menhaden Hotel
3 4
hotel , Greenport
The Menhaden Hotel is situated in Greenport, just 26 miles from Splish Splash water park and 47 miles from Long Island MacArthur Airport, making it an ideal base for exploring the charming waterfront town. This 4-star hotel boasts excellent user ratings for its location, cleanliness, and overall experience. The hotel offers comfortable rooms with private bathrooms and modern amenities, including air conditioning, free Wi-Fi, and flat-screen TVs. Guests can enjoy the on-site restaurant and bar, relax on the terrace, or explore the area on complimentary bikes.
8.7 1000 reviews
Southold, NY
05/07 – 09/07
A$2314/nighttotal: A$9256 (4 )
The Harbor Front Inn
3 4
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.
8.8 431 reviews
Southold, NY
05/07 – 09/07
A$2387/nighttotal: A$9548 (4 )
The Harbor Front Inn
3 4
hotel , Greenport
The Harbor Front Inn, a 3.5-star hotel in Greenport, offers a prime location with waterfront access and proximity to local attractions. This pet-friendly accommodation provides complimentary Wi-Fi, an on-site swimming pool, a fitness centre, and rooms featuring balconies or terraces, with select rooms offering separate living areas and all including streaming video and daily newspapers.
9.0 484 reviews
Southold, NY
05/07 – 09/07
A$4919/nighttotal: A$19676 (4 )
Faraway Sag Harbor
2 4
hotel , Sag Harbor
Baron's Cove is located in Sag Harbor, New York, just a short drive from Montauk and Mystic, offering a convenient base for exploring the charming Hamptons. This 4-star hotel has received very good user ratings for its location, cleanliness, and overall experience. The accommodation has a range of rooms with either ocean or garden views. Guests can enjoy a saltwater swimming pool, on-site restaurant, bike hire, a shop, and a range of other amenities including a spa, fitness centre, and tennis court.
Best Southold, NY luxury hotels (4 and 5 stars)
Among the 14 accommodations in Southold, NY, here are the 4 best luxury hotels
9.0 484 reviews
Southold, NY
05/07 – 09/07
A$4919/nighttotal: A$19676 (4 )
Faraway Sag Harbor
2 4
hotel , Sag Harbor
Baron's Cove is located in Sag Harbor, New York, just a short drive from Montauk and Mystic, offering a convenient base for exploring the charming Hamptons. This 4-star hotel has received very good user ratings for its location, cleanliness, and overall experience. The accommodation has a range of rooms with either ocean or garden views. Guests can enjoy a saltwater swimming pool, on-site restaurant, bike hire, a shop, and a range of other amenities including a spa, fitness centre, and tennis court.
9.6 273 reviews
Southold, NY
05/07 – 09/07
A$3213/nighttotal: A$12852 (4 )
The Menhaden Hotel
3 4
hotel , Greenport
The Menhaden Hotel is situated in Greenport, just 26 miles from Splish Splash water park and 47 miles from Long Island MacArthur Airport, making it an ideal base for exploring the charming waterfront town. This 4-star hotel boasts excellent user ratings for its location, cleanliness, and overall experience. The hotel offers comfortable rooms with private bathrooms and modern amenities, including air conditioning, free Wi-Fi, and flat-screen TVs. Guests can enjoy the on-site restaurant and bar, relax on the terrace, or explore the area on complimentary bikes.
8.5 82 reviews
Southold, NY
05/07 – 09/07
A$1897/nighttotal: A$7588 (4 )
Shelter Island House
3 4
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.
9.3 215 reviews
Southold, NY
05/07 – 09/07
A$2882/nighttotal: A$11528 (4 )
The Pridwin Hotel
3 4
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.
Best Southold, NY hotels with a pool
Among the 14 accommodations in Southold, NY, here are the 4 best hotels with a pool
8.3 942 reviews
Southold, NY
05/07 – 09/07
A$1975/nighttotal: A$7900 (4 )
Sound View Greenport
2 4
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.
9.3 844 reviews
Southold, NY
05/07 – 09/07
A$1134/nighttotal: A$4536 (4 )
Sag Harbor Inn
1 4
hotel , Sag Harbor
The Sag Harbor Inn is located in Sag Harbor, a short distance from Havens Beach and within easy reach of attractions like Montauk Point Lighthouse. The hotel has consistently received excellent ratings for its location, cleanliness, and overall guest experience. The inn offers comfortable rooms with a choice of layouts, including single-bedroom options with a floor area of 36 square metres. Amenities include a seasonal outdoor pool, a shared lounge, free private parking, and a continental breakfast served each morning.
8.8 431 reviews
Southold, NY
05/07 – 09/07
A$2387/nighttotal: A$9548 (4 )
The Harbor Front Inn
3 4
hotel , Greenport
The Harbor Front Inn, a 3.5-star hotel in Greenport, offers a prime location with waterfront access and proximity to local attractions. This pet-friendly accommodation provides complimentary Wi-Fi, an on-site swimming pool, a fitness centre, and rooms featuring balconies or terraces, with select rooms offering separate living areas and all including streaming video and daily newspapers.
8.5 82 reviews
Southold, NY
05/07 – 09/07
A$1897/nighttotal: A$7588 (4 )
Shelter Island House
3 4
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.
Frequently asked questions about hotels in Southold, NY
How can travelers relax during a week in and arond Southold, NY?
Southold is all about slowing down and enjoying the simple pleasures. Spend your days exploring the beaches, like the one at Orient Point State Park. Rent a bike and cycle along the scenic roads, or simply relax with a good book at a local cafe. In the evenings, enjoy the sunset over the Long Island Sound from one of the many waterfront restaurants.
What are the best hotels with a swimming pool in Southold, NY?
What amenities can travelers expect in hotel rooms in Southold, NY?
Hotel rooms in Southold typically offer basic amenities like comfortable beds, air conditioning, and private bathrooms. Some hotels may also have additional features like swimming pools, fitness centres, or complimentary breakfast. However, it's always best to check the specific amenities offered by each hotel before booking.
What are the most popular 2, 3 and 4-star hotels in Southold, NY?
When is the best time to book a hotel in Southold, NY?
The best time to book a hotel in Southold is during the shoulder seasons, from April to May or September to October, when the weather is still pleasant but the crowds are smaller. You'll also find better deals on accommodation during these months.
What are some pet-friendly activities in and around Southold, NY?
Southold is a dog-friendly destination. Many of the beaches, like the one at Orient Point State Park, allow dogs on leash, and there are plenty of dog-friendly restaurants and cafes. You can also take your furry friend for a walk along the scenic Southold waterfront or explore the nearby nature trails.
What are the best family friendly hotels in Southold, NY?
Which towns or cities worth a visit near Southold, NY?
Greenport, just a short drive from Southold, is a charming waterfront village with a vibrant arts scene and a lively nightlife. Mattituck, known for its vineyards and farm stands, is another great option for a day trip. If you're looking for a more urban experience, you can visit the city of Riverhead, which is home to a variety of shops, restaurants, and attractions.
What are the best pet friendly hotels in Southold, NY?
Sound View Greenport, a four-star hotel in Greenport, NY, offers a prime location on the coastline with excellent access to local attractions. This family-friendly establishment provides complimentary breakfast, free Wi-Fi, on-site parking, concierge and ticket services, room service, a swimming pool with a poolside bar, and tennis courts, alongside a restaurant and bar.
9.2 522 reviews
Southold, NY
05/07 – 09/07
A$1691/nighttotal: A$6764 (4 )
American Beech Hotel
2 4
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.
9.6 273 reviews
Southold, NY
05/07 – 09/07
A$3213/nighttotal: A$12852 (4 )
The Menhaden Hotel
3 4
hotel , Greenport
The Menhaden Hotel is situated in Greenport, just 26 miles from Splish Splash water park and 47 miles from Long Island MacArthur Airport, making it an ideal base for exploring the charming waterfront town. This 4-star hotel boasts excellent user ratings for its location, cleanliness, and overall experience. The hotel offers comfortable rooms with private bathrooms and modern amenities, including air conditioning, free Wi-Fi, and flat-screen TVs. Guests can enjoy the on-site restaurant and bar, relax on the terrace, or explore the area on complimentary bikes.
8.5 82 reviews
Southold, NY
05/07 – 09/07
A$1897/nighttotal: A$7588 (4 )
Shelter Island House
3 4
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 balcony
8.7 1000 reviews
Southold, NY
05/07 – 09/07
A$2314/nighttotal: A$9256 (4 )
The Harbor Front Inn
3 4
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.
9.0 484 reviews
Southold, NY
05/07 – 09/07
A$4919/nighttotal: A$19676 (4 )
Faraway Sag Harbor
2 4
hotel , Sag Harbor
Baron's Cove is located in Sag Harbor, New York, just a short drive from Montauk and Mystic, offering a convenient base for exploring the charming Hamptons. This 4-star hotel has received very good user ratings for its location, cleanliness, and overall experience. The accommodation has a range of rooms with either ocean or garden views. Guests can enjoy a saltwater swimming pool, on-site restaurant, bike hire, a shop, and a range of other amenities including a spa, fitness centre, and tennis court.
8.8 431 reviews
Southold, NY
05/07 – 09/07
A$2387/nighttotal: A$9548 (4 )
The Harbor Front Inn
3 4
hotel , Greenport
The Harbor Front Inn, a 3.5-star hotel in Greenport, offers a prime location with waterfront access and proximity to local attractions. This pet-friendly accommodation provides complimentary Wi-Fi, an on-site swimming pool, a fitness centre, and rooms featuring balconies or terraces, with select rooms offering separate living areas and all including streaming video and daily newspapers.
8.2 315 reviews
Southold, NY
05/07 – 09/07
A$3322/nighttotal: A$13288 (4 )
Sound View Greenport
3 4
hotel , Greenport
Sound View Greenport, a four-star hotel in Greenport, NY, offers a prime location on the coastline with excellent access to local attractions. This family-friendly establishment provides complimentary breakfast, free Wi-Fi, on-site parking, concierge and ticket services, room service, a swimming pool with a poolside bar, and tennis courts, alongside a restaurant and bar.