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Hotels in Southold

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  • The Pridwin Hotel

    3 Stars

    The Pridwin Hotel

    81 Shore Road (to 4.30 km)

    Located on Crescent Beach, this Shelter Island hotel boasts an outdoor pool overlooking the bay, a private beach, free Wi-Fi and rooms with cable TV. The North Ferry is 2 miles away. Rooms at The Pridwin Hotel offer air-conditioning and an en-suite bathroom with free toiletries and a hair dryer. The seasonal on-site restaurant and bar lounge serves American fare and features entertainment on select nights during summer months. Guests staying at The Pridwin Hotel - Shelter Island can enjoy two docks with boats like kayaks, rowboats and more available for hire. The South Ferry is 11 minutes’ drive away. The Mashomack Preserve is 5 miles away. On Crescent Beach, this Shelter Island hotel has an outdoor pool overlooking the bay, a private beach, free Wi-Fi and rooms with cable TV. The North Ferry is 2 miles from the property. The rooms at The Pridwin Hotel have air conditioning and a private bathroom with free toiletries and a hairdryer. The seasonal on-site restaurant and bar lounge serves American cuisine and features entertainment on select nights during summer months. Guests staying at The Pridwin Hotel - Shelter Island can enjoy 2 docks with boats like kayaks, rowboats and more available for rent. The South Ferry is an 11-minute drive from the property. The Mashomack Preserve is 5 miles from the hotel.

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  • Sunset Beach

    4 Stars

    Sunset Beach

    35 Shore Road (to 5.17 km)

    This beachfront boutique hotel boasts the Sunset Beach Restaurant and Bar and rooms with a flat-screen LCD TV. It is just 2 miles from the ferry to Greenport. With a balcony overlooking the Shelter Island Sound, each modern room at Sunset Beach is equipped with an iPod docking station, DVD player, and free Wi-Fi. The rooms are furnished with hardwood floors and glass-topped tables. Yoga sessions and in-room massages are available at Sunset. Guests can spend the day on the private beach or explore the island with free bicycle rentals. This pet-friendly property also offers grooming services. Open for breakfast, lunch, and dinner, Sunset Beach Restaurant and Bar serves French cuisine in a casual atmosphere. It also features a full-service bar and a wine list. The Shelter Island Country Club is 1.5 miles from the Shelter Island Sunset Beach Hotel. Shelter Island Yacht Club is within a 10-minute drive. This beachfront boutique hotel boasts the Sunset Beach Restaurant and Bar and rooms with a flat-screen LCD TV. It is just 2 miles from the ferry to Greenport. With a balcony overlooking the Shelter Island Sound, each modern room at Sunset Beach is equipped with an iPod docking station, DVD player, and free Wi-Fi. The rooms are furnished with hardwood floors and glass-topped tables. Yoga sessions and in-room massages are available at Sunset. Guests can spend the day on the private beach or explore the island with free bicycle rentals. This pet-friendly property also offers grooming services. Open for breakfast, lunch, and dinner, Sunset Beach Restaurant and Bar serves French cuisine in a casual atmosphere. It also features a full-service bar and a wine list. The Shelter Island Country Club is 1.5 miles from the Shelter Island Sunset Beach Hotel. Shelter Island Yacht Club is within a 10-minute drive.

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  • Seven - Shelter Island Guest House

    Seven - Shelter Island Guest House

    7 Stearns Point Road (to 5.59 km)

    Just 500 metres from the Shelter Island Country Club, this bed and breakfast with rooms with a TV in Shelter Island Heights. A free breakfast is served each morning at the on-site restaurant. Cable channels are provided in each room at SEVEN – Shelter Island Guest House. Featuring a seating area, rooms also include a private bathroom with a hairdryer and free toiletries. An outdoor pool and an on-site garden provide perfect places for guests to relax at SEVEN – Shelter Island Guest House. WiFi access and on-site parking are provided free of charge. South Ferry is just 6.5 km from the BB, which is 400 metres from the beach on the Peconic River. Mashomack Preserve is 10 minutes’ drive away.

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  • The Stirling House Bb Greenport

    4 Stars

    The Stirling House B&b Greenport

    104 Bay Avenue (to 7.35 km)

    This Greenport bed and breakfast is located on the water and offers free Wi-Fi and individually decorated rooms equipped with electric fireplaces. Island’s End Golf Country Club is 2 miles away. A flat-screen TV is offered in each uniquely decorated room at The Stirling House BB Greenport. An en suite bathroom is also included. A full gourmet breakfast is served each morning in the dining area and on the front terrace overlooking the water. The Greenport Stirling House BB is a half mile from the beach area. A ferry service is also available to Shelter Island.

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  • Cedar House On Sound Bb

    3 Stars

    Cedar House On Sound B&b

    4850 Sound Avenue (to 14.68 km)

    Located in the heart of wine country, this Long Island bed and breakfast boasts an on-site vineyard and free wine tasting. A fresh two-course breakfast is prepared daily. Each uniquely styled guest room at the Cedar House on Sound BB features a 32-inch flat-screen TV, iPod dock, and an en suite bathroom. Decorated in warm colours, the rooms offer views of the courtyard garden. A common room with billiards, board games, and flat-screen TV is provided for entertainment. Tour the barns or relax on the back patio overlooking the property. Free Wi-Fi is available throughout the BB. Enjoy 24-hour coffee and tea at the Cedar House BB. The Vineyard Lounge offers a large wine selection. Breakwater Beach District Park is 3 miles from the bed and breakfast. Hallockville Museum Farm is 5 minutes’ drive away. In the heart of wine country, this Long Island bed and breakfast features an on-site vineyard and free wine tasting. A fresh two-course breakfast is prepared daily. Each uniquely-styled guest room at the Cedar House on Sound BB features a 32-inch flat-screen TV, iPod dock, and a private bathroom. Decorated in warm colors, the rooms provide views of the courtyard garden. A common room with billiards, board games, and flat-screen TV is provided for entertainment. Tour the barns or relax on the back patio overlooking the property. Free Wi-Fi is available throughout the bed and breakfast. Enjoy 24-hour coffee and tea at the Cedar House BB. The Vineyard Lounge offers a large wine selection. Breakwater Beach District Park is 3 miles from the bed and breakfast. Hallockville Museum Farm is a 5 minute drive away.

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