Our top 12 properties

based on 188 guest reviews
Southold 2.3 miles from center
9.3 Superb
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Offering air-conditioned rooms and a terrace, A Walk in the Woods Bed and Breakfast is located 2.3 miles from the center of Southold and offers superb, 3-star, superbly rated hospitality, with 6 well-appointed, air-conditioned, en-suite rooms. Check out 3 stay deals at up to 30% OFF on selected nights in February and March, plus the bed and breakfastis rated 9.3 out of 10 from 42 fully verified guest reviews. more
Free Parking Free Wi-Fi Restaurant Billiards
Southold 0.8 miles from center
New
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Classic Southold Country Charmer is ideally located 0.8 miles from the center of Southold and offers excellent accommodation, with 2 spacious, tastefully appointed, air-conditioned bedrooms, sleeping up to 4 guests. Check out 2 vacation deals at up to 28% OFF on selected nights in February and March. more
Free Parking No Smoking Rooms Free Wi-Fi
Southold 0.8 miles from center
8.7 Fabulous
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Boasting a yard, air-conditioned rooms and is pet friendly, Historic White Blossom House is ideally situated 0.8 miles from the center of Southold and offers highly rated accommodation, with 4 tastefully furnished, air-conditioned bedrooms, sleeping up to 8 guests. Check out 6 apartment deals at up to 28% OFF on selected nights in February and March, plus the apartment is rated 8.7 out of 10 from 14 fully verified guest reviews. more
Free Parking Free Wi-Fi Family Rooms Pets Welcome Tennis
Southold 1.4 miles from center
9.1 Superb
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The Shoals Suites & Slips Hotel is ideally located 1.4 miles from the center of Southold and offers superior, 4-star, highly rated hotel accommodation, with 19 bright & generously appointed, air-conditioned rooms. Check out 4 room deals at up to 37% OFF on selected nights in February and March, plus the hotel is rated 9.1 out of 10 from 58 fully verified guest reviews. more
Free Parking Free Wi-Fi Restaurant
Southold 1.7 miles from center
8.4 Very good
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Offering a sun terrace, the Southold Beach Motel is situated 1.7 miles from the center of Southold and offers very well-rated accommodation, with 13 bright & airy, air-conditioned rooms. Check out 4 stay deals at up to 36% OFF on selected nights in February and March, plus the property is rated 8.4 out of 10 from 38 fully verified guest reviews. more
Free Parking Family Rooms
Southold 130 yards from center
9.8 Exceptional
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With 2 en-suite rooms, Wickham-Prince Bed And Breakfast is set in Southold and offers great, 2-star, superior-rated hospitality, with two tastefully appointed, air-conditioned, en-suite rooms. Check out 3 stay deals at up to 25 % OFF on selected nights in February and March, plus the bed and breakfastis rated 9.8 out of 10 from 36 fully verified guest reviews. more
Free Parking Free Wi-Fi Restaurant
8.9 Fabulous
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The Pridwin is a waterfront reso... more
Free Parking Free Wi-Fi Family Rooms Restaurant Outdoor Pool Accessible Rooms Gym Tennis SPA
8.1 Very good
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Set on the North Fork in Greenpo... more
Valet Parking Free Wi-Fi Family Rooms Restaurant Bar Pets Welcome Outdoor Pool Accessible Rooms Gym Tennis
9.6 Exceptional
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Located in Greenport, 26 miles f... more
Free Parking Free Wi-Fi Restaurant Bar Pets Welcome Outdoor Pool Accessible Rooms Gym
9.5 Superb
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Set in Greenport, 27 miles from... more
Free Parking Free Wi-Fi Restaurant Bar Accessible Rooms
4.0 Review score
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Shelter Island House features a... more
Free Parking Free Wi-Fi Family Rooms Restaurant Bar Outdoor Pool
7.9 Good
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Featuring a 1950’s retro décor,... more
Free Parking Free Wi-Fi Family Rooms Restaurant Bar Outdoor Pool Accessible Rooms
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FAQs

  • Can I book a hotel in Southold and pay later?

    Yes, you can book a hotel in Southold today and pay when you stay at 95% of our Southold properties for advance bookings. Most bookings require a card to secure your booking, but in most cases, you will pay at the hotel.

  • Can I book a hotel in Southold without a deposit?

    Most of our hotels in Southold can be booked without a deposit. In most cases, you will only need your card to guarantee your rooms, with payment being taken at the hotel.

  • Can you stay at a hotel in Southold and pay later?

    You can plan your stay and book your hotel in Southold without paying upfront at most of our hotels. You can pay for your hotel once you arrive or before you check-out on most advance bookings. You also get free cancelations at most hotels when you book in advance.

  • Can you pay hotels in Southold with cash?

    You can pay cash at most hotels in Southold for your trip, with some hotels requiring no card at the time of booking. However, most hotels will need a card to complete your booking but will only use it for guaranteeing your room. Most hotels will welcome payment of your bill with cash.

  • Can i cancel my booking without any charges?

    95% of our hotels in Southold offer free cancellation on advance bookings. Check the conditions of the rooms you want to book, and choose a deal that includes free cancellation.

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