Southold

Travel Guide

Southold
Photo by Benny Goh
Photo by Benny Goh
Photo by Benny Goh
Photo by Benny Goh
Photo by 4 Star Traveler
Photo by 4 Star Traveler
Photo by 4 Star Traveler
Photo by 4 Star Traveler
The Shoals Suites and Slips

The Shoals Suites and Slips

3.5 out of 5
61600 Main Rd, Southold, NY
The price is RM1,023 per night from 22 Oct to 23 Oct
RM1,023
RM1,275 total
22 Oct - 23 Oct
includes taxes & fees
Stay at this 3.5-star hotel in Southold. Enjoy free WiFi, free bicycles on site, and a business center. Our guests praise the helpful staff in our reviews. Popular ...
9.4/10 Exceptional! (214 reviews)
"This property was insanely clean and well kept. Location lovely and close to restaurants wineries and farms to visit. Scenery pretty . Wished they had one more fire pit!"

Reviewed on 13 Oct 2025

The Shoals Suites and Slips
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 RM338 per night from 22 Oct to 23 Oct
RM338
RM389 total
22 Oct - 23 Oct
includes taxes & fees
Stay at this hotel in Old Saybrook. Enjoy free WiFi, free parking, and a picnic area. Our guests praise the helpful staff and the clean rooms in our reviews. ...
7.8/10 Good! (1,014 reviews)
"We had a quick stop in the area and picked this hotel. We weee pleasantly surprised! It’s rare to find a small private hotel maintained like a corporate hotel. This is a good one."

Reviewed on 13 Oct 2025

Pier Blue Inn Old Saybrook - Essex
Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

3.5 out of 5
2 Bridge St, Old Saybrook, CT
The price is RM1,015 per night from 6 Nov to 7 Nov
RM1,015
RM1,273 total
6 Nov - 7 Nov
includes taxes & fees
Stay at this 3.5-star spa hotel in Old Saybrook. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the restaurant and the helpful staff in ...
9.4/10 Exceptional! (1,012 reviews)
"Location"

Reviewed on 14 Oct 2025

Saybrook Point Resort & Marina
See all 4,317 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.
Cliffside Resort Condominiums

Cliffside Resort Condominiums

3 out of 5
61475 Route 48 (North Road), Greenport, NY
Stay at this 3-star beach aparthotel in Greenport. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Railroad Museum of Long Island and ...
8.8/10 Excellent! (243 reviews)
"Nice location and good for staying with families. The rooms could have been a little cleaner and updated. Hotel communication was excellent for checking in."

Reviewed on 11 Oct 2025

Cliffside Resort Condominiums
Windward Shores Ocean Resort

Windward Shores Ocean Resort

3 out of 5
2062 Montauk Highway, PO Box 7031, Amagansett, NY
Stay at this 3-star beach aparthotel in Amagansett. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff and the clean rooms ...
8.6/10 Excellent! (298 reviews)
"The property and walk to the beach were great! The condo was exactly what we needed but could use a facelift. While it was clean, the decor and fixtures were dated."

Reviewed on 13 Oct 2025

Windward Shores Ocean Resort
See all 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.

Popular places to visit

Sparkling Pointe

Sparkling Pointe

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.

Sparkling Pointe

Sannino's Bella Vita Vineyard

You can enjoy a tasting or tour at Sannino's Bella Vita Vineyard during your travels to Southold. Wander the beaches or discover the sunsets in this family-friendly area.

Sannino's Bella Vita Vineyard

Croteaux Vineyards

You can enjoy a tasting or tour at Croteaux Vineyards during your travels to Southold. Wander the beautiful beaches in this family-friendly area.

Croteaux Vineyards

Osprey's Dominion

You can enjoy a tasting or tour at Osprey's Dominion during your travels to Southold. Wander the beautiful beaches in this family-friendly area.

Osprey's Dominion

Corey Creek Winery

You can enjoy a tasting or tour at Corey Creek Winery during your travels to Southold. Wander the beautiful beaches in this family-friendly area.

Corey Creek Winery

Horton Point Park

Explore the great outdoors at Horton Point Park, a lovely green space in Southold. Wander the beaches or discover the sunsets in this family-friendly area.

Horton Point Park

Things to do

Join a small group full-day wine tour with a certified Sommelier host

Long Island Wine and Food Day Trip with Sommelier host from NYC

RM626
per adult
Long Island Wine and Food Day Trip with Sommelier host from NYC
Picture 1 for Activity From Mattituck: North Fork Area Bike Tour with Food Tasting

From Mattituck: North Fork Area Bike Tour with Food Tasting

RM588
per adult
From Mattituck: North Fork Area Bike Tour with Food Tasting
See all activities in Southold