Southold

Travel Guide

A calm lake with a forest in the background during sunset.
A calm lake with tall grasses in the foreground and a forested shoreline under a pink sky.
A river with red vegetation and a forest in the background.
A lifeguard tower, a boat, and a sandy beach with the ocean in the background.
A river with boats, a marina, and residential areas.
The Shoals Suites and Slips

The Shoals Suites and Slips

3.5 out of 5
61600 Main Rd Southold NY
The price is €338 per night from 1 Sept to 2 Sept
€338
1 Sept - 2 Sept
includes taxes & fees
Stay at this hotel in Southold. Enjoy free Wi-Fi, free bicycles on-site and a business centre. Our guests praise the helpful staff in their reviews. Popular ...
The Shoals Suites and Slips
Vine & Sand

Vine & Sand

3 out of 5
47100 New York 25 Southold NY
Stay at this business-friendly B&B in Southold. Enjoy free breakfast, free Wi-Fi and free parking. Popular attractions Mattebella Vineyards and Croteaux Vineyards ...
9.8/10 Exceptional! (20 reviews)
"The hosts were very friendly and welcoming. They were always available when we had questions or needed anything. We enjoyed the fresh pastries and fresh fruit the 1st morning. They were very accommodating and had breakfast out early when we had to leave extra early for our event our 1st day."

Reviewed on 24 Jun 2026

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Vine & Sand
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
1430 Boston Post Rd Old Saybrook CT
The price is €98 per night from 10 Aug to 11 Aug
€98
10 Aug - 11 Aug
includes taxes & fees
Stay at this hotel in Old Saybrook. Enjoy free Wi-Fi, free parking and a picnic area. Our guests praise the helpful staff and the clean rooms in their reviews. ...
Pier Blue Inn Old Saybrook - Essex
See all 4,368 properties in Southold
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Perfect Waterfront Family Vacation Home next to the best vineyards in NY!

Perfect Waterfront Family Vacation Home next to the best vineyards in NY!

Southold NY
Stay at this beach holiday home in Southold. Enjoy free Wi-Fi, a beach locale and a garden. Popular attractions Croteaux Vineyards and Mattebella Vineyards are ...
10/10 Exceptional! (41 reviews)
"We had the most wonderful stay at this property and knew from the moment we walked in that it was something special. The house has real charm and soul. You can tell it was put together with care and love, not just decorated to look nice in photos. Every detail felt intentional.The outdoor space was ..."

Reviewed on 30 Jul 2026

Perfect Waterfront Family Vacation Home next to the best vineyards in NY!
North Fork Resort

North Fork Resort

3 out of 5
690 Queen St Greenport NY
Stay at this cottage in Greenport. Enjoy free Wi-Fi, free parking and an outdoor pool. Popular attractions Railroad Museum of Long Island and Greenport Farmers' ...
North Fork Resort
Cliffside Resort Condominiums

Cliffside Resort Condominiums

3 out of 5
61475 Route 48 (North Road) Greenport NY
Stay at this beach aparthotel in Greenport. Enjoy free Wi-Fi, free parking and an outdoor pool. Popular attractions Railroad Museum of Long Island and East End ...
9/10 Wonderful! (281 reviews)
"Nice decoration !!"

Reviewed on 6 Aug 2026

Cliffside Resort Condominiums
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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Stay near popular Southold attractions

Sparkling Pointe

8.8/10 (11 reviews)
You can enjoy a tasting or tour at Sparkling Pointe during your travels to Southold. Discover the sunsets and wineries in this family-friendly area.
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Things to do

Public Schooner Sail in Greenport

Sunday Brunch Sail in Greenport

€153
per adult
Sunday Brunch Sail in Greenport
See all activities in Southold
A pebbled beach with a sunset and a distant bridge.

Shelter Island Heights

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