5/5 - Excellent
Verified traveler
Head into Greenport for the brewery, Aldo’s for coffee, Crazy Beans, and the waterfront. Pindar vineyard was a great time and there is a nice family farm directly across the street.
Southold, NY
Travel Guide
Visit Southold
The Shoals Suites and Slips
61600 Main Rd Southold NY
The price is ￥25,558 per night from Jan 11 to Jan 12
￥25,558
￥29,201 total
Jan 11 - Jan 12, 2026
includes taxes & fees
Stay at this hotel in Southold. Enjoy free WiFi, free bicycles on site, and a business center. Our guests praise the helpful staff in our reviews. Popular attractions ...
9.4/10 Exceptional! (232 reviews)
Overall excellent experience during the off-season at this new seaside hotel…Large rooms with separate kitchen/living room areas, modern and elegant, friendly check-in service, and expansive lobby area with lots of seating and spectacular water views.
Reviewed on Dec 23, 2025
Water's Edge Resort & Spa
1525 Boston Post Road Westbrook CT
The price is ￥35,855 per night from Jan 4 to Jan 5
￥35,855
￥43,935 total
Jan 4 - Jan 5, 2026
includes taxes & fees
Book a stay at this beach resort in Westbrook. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular ...
8.8/10 Excellent! (1,000 reviews)
Wonderful hotel with very courteous staff, Water's Edge is top notch in every way
Reviewed on Dec 26, 2025
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
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! (1,001 reviews)
This hotel is clean and safe. Parking was easy. Rooms are spacious. Staff was friendly. It's not overly fancy but was perfect for a reasonable price.
Reviewed on Dec 23, 2025
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.
Beautifully farmhouse
Southold NY
Book a stay at this family-friendly vacation home in Southold. Enjoy free WiFi, a water park, and a garden. Popular attractions Sparkling Pointe and The Old ...
10/10 Exceptional! (3 reviews)
We spent a few days to attend a family wedding. We were 7 and the house was extremely comfortable for all of us. The house is 2 floors and there is no bathroom upstairs so keep that in mind when assigning sleeping arrangements. We found a well stocked welcome basket and a bottle of wine which were ...
Reviewed on Sep 8, 2025
“Paradise Found” - Walk to Private Beach & In-Ground Pool!
Southold NY
Book a stay at this family-friendly vacation home in Southold. Enjoy a garden, laundry facilities, and patios. Popular attractions Croteaux Vineyards and Custer ...
10/10 Exceptional! (7 reviews)
We had a great stay. We enjoyed cooking in the beautiful kitchen and spending time with family. We hope to visit again!
Reviewed on Dec 19, 2025
WHB Village,4200sqft,Traffic Free,Private Dr,40ft Heated Pool OPEN,Beach,Fam Fr
Westhampton Beach NY
Book a stay at this family-friendly vacation home in Westhampton Beach. Enjoy private pools, a garden, and laundry facilities. Popular attractions Westhampton ...
9.8/10 Exceptional! (189 reviews)
Was the perfect place for our family with 3 adults and 3 teenage who each had their own rooms. Very convenient location and the host gave us lots of suggestions. Definitely recommend anyone looking for a place to stay to stay here. We plan on going back next year!
Reviewed on Dec 24, 2025
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
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.
The Old Field Vineyards
You can enjoy a tasting or tour at The Old Field Vineyards during your travels to Southold. Stroll along the beaches or discover the sunsets in this family-friendly area.
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.
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.
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.
Horton Lane Beach
Why not spend a lazy afternoon at Horton Lane Beach during your trip to Southold? Stroll along the beaches or discover the area's sunsets.
Things to do
The Hamptons, Sag Harbor & Outlet Shopping Day Trip from NYC
￥27,804
per adult
76% of travellers recommend
Reviews of Southold
4.4
Top Destination
3/5 - Okay
Verified traveler
Expensive
5/5 - Excellent
Verified traveler
I love Southold and all the areas on the Northfork side.
5/5 - Excellent
Verified traveler
Quiet, North Fork town.
3/5 - Okay
Louise
Lots of wineries to visit with excellent wines. Tastings can be a bit expensive. One vineyard charged $16 for 3 - 2 oz tastings. It would have been less expensive to just buy a glass or a bottle of wine. A glass of wine was $11 - $13.
4/5 - Good
Trish
Took a wonderful Jet Ski tour around Shelter Island (Peconic Water Sports), Spent a wonderful day in Greenport.
Explore a world of travel with Expedia
- Vacation Homes in North Fork
- All-Inclusive Hotel Hotels in Montauk
- Hotels with Hot Tubs in Montauk
- Hostels in Montauk
- Resorts in Westhampton Beach
- Hotels with a Pool in Shelter Island
- Hotels near Montauk Downs State Park Golf Course
- Resorts in Riverside
- Chalets in South Jamesport
- Luxury Hotels in Flanders
- Beach Hotels in Beach Hampton
- Boutique Hotels in Village of East Hampton
- Resorts in Montauk
- Resorts in Shelter Island
- Motels in Riverhead
- Cheap Hotels in East Hampton
- Aparthotels in Amagansett
- B&B in Southampton
- Boutique Hotels in East Hampton
- Historic Hotels in Montauk
- Guest Houses in Village of East Hampton
- Sag Harbor Hotels
- East Hampton Hotels
- Resorts in Noyack
- Orient Point Hotels
- Hotels near Cooper's Beach
- Palaces in Southampton
- Aparthotels in Noyack
- Hotels near Ponquogue Beach
- Cheap Hotels in Montauk
- Beach Hotels in Hamptons
- Vacation Homes in Westhampton Beach
- Cheap Hotels in Hamptons
- Cheap Hotels in Peconic
- Beach Hotels in Montauk
- Motels in Southold
- Town Houses in Montauk
- Hotels near Riverhead Station
- Beach Hotels in Westhampton Beach
- Cheap Hotels in North Fork
- Inns in Southampton
- Hotels with Hot Tubs in Shelter Island
- Town of Southampton Hotels
- Town Houses in Sag Harbor
- Boutique Hotels in Sag Harbor
- Rv Parks in North Fork
- Motels in Wading River
- Villas in Hamptons
- Resorts in Orient
- Holiday Park Resorts in Montauk
- Southampton Hotels
- Inns in Riverhead
- Luxury Hotels in Lion Head Beach
- Residences in Shinnecock Reservation
- Inns in Bridgehampton
- Remsenburg Hotels
- Aparthotels in Laurel
- Cheap Hotels in Riverhead
- Hotels near Brookhaven National Laboratory
- Hotels near Kirk Park Beach
- Villas in Shelter Island
- Hostels in Shinnecock Reservation
- Luxury Hotels in Montauk
- Inns in Sagaponack
- Resorts in Rocky Point
- Beach Hotels in Suffolk County
- Cheap Hotels in South Fork
- Hotels near East Hampton Main Beach
- Vacation Homes in Hamptons
- Houseboats in Springs
- Silver Beach Hotels
- Residences in Sagaponack
- Hotels near The Hamptons Beaches
- Residences in Greenport
- B&B in Montauk
- Beach Hotels in East Hampton North
- Castles in Southampton
- Vacation Homes in East Hampton
- Winery Hotels in Riverhead
- Riverside Hotels
- Resorts in Springs
- Resorts in Ridge
- Montauk Hotels
- Cheap Hotels in Laurel
- Riads in Fishers Island
- Aparthotels in Hamptons
- Apartments in Speonk
- Flanders Hotels
- Amagansett Hotels
- Boutique Hotels in Montauk
- Inns in Village of Southampton
- Cheap Hotels in Suffolk County
- Vacation Homes in Baiting Hollow
