Southold Vacation Packages
Book a Stay + Flight or Car to save on your trip
Top Southold vacation package deals
Price found within the past 48 hours. Click for updated prices.
4.5-star property
The Gotham Hotel
Manhattan
9.2/10 Wonderful! (1,051 reviews)
Dec 2 - Dec 5
3 night stay
Atlanta (ATL) to New York (JFK)
Delta • Coach
New York (JFK) to Atlanta (ATL)
Frontier Airlines • Coach
Save 100% on your flight
Price was $1,673, price is now $997 per person
$997
per person
found 1 day ago
The hotel felt modern, clean and spacious. Slightly noisy at night but that's Midtown. Couldn't access the hotel bar either night because of private events. Staff were polite and helpful. Would definitely recommend.
Reviewed on Sep 25, 2026
5.0-star property
Park Lane New York
Manhattan
8.4/10 Very Good! (1,804 reviews)
Nov 19 - Nov 22
3 night stay
Atlanta (ATL) to New York (JFK)
Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,264, price is now $803 per person
$803
per person
found 1 day ago
A very average experience for the money paid.
Reviewed on Sep 25, 2026
Top rated hotels for your Southold vacation package
The Shoals Suites and Slips
61600 Main Rd Southold NY
1.41 mi from city center
$254 nightly
The price is $286 total per night
$286 total
Oct 1 - Oct 2
Total with taxes and fees
Guests of The Shoals Suites and Slips enjoy features like a business center, free use of bicycles and a computer station. Front-desk staff can assist with concierge services, luggage storage, and securing valuables. Additional amenities include express check-out, a ballroom, and wedding services.
Free WiFi
Restaurant
Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
Free Cancellation
15.32 mi from city center
$91 nightly
The price is $104 total per night
$104 total
Oct 5 - Oct 6
Total with taxes and fees
Pier Blue Inn Old Saybrook - Essex features free WiFi in public areas and a picnic area. Free parking is included with your stay. Staff members can answer questions about accommodations, and also provide front-desk service during limited hours. If you like to take your furry friend along on your adventures, this pet-friendly property offers an off-leash area.
Pet friendly
Parking included
Water's Edge Resort & Spa
1525 Boston Post Road Westbrook CT
Free Cancellation
Reserve now, pay when you stay
14.97 mi from city center
$218 nightly
The price is $251 total per night
$251 total
Oct 7 - Oct 8
Total with taxes and fees
Guests of Water's Edge Resort & Spa have access to a private beach, a full-service spa, and an indoor pool. You can put free valet parking to good use if you drive. The 24-hour front desk has staff standing by to help with tours or tickets, securing valuables, and luggage storage. Other amenities at this beach resort include a gym, a sauna, and outdoor tennis courts.
On private beach
Pool
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.
Things to do
Explore More Ways to Travel with Travelocity
- Hotels near Peconic Bay Winery
- Hotels near Waters Crest Winery
- Beach Resorts & in Town of Southold Town
- Hotels with Pool in Town of Southold Town
- Hotels near Pindar Vineyards
- Hotels near Sannino's Bella Vita Vineyard
- Hotels near Raphael Winery
- Cottages in Southold Station
- Motels in Southold Station
- Hotels near 8 Hands Farm
- Hotels near Croteaux Vineyards
- Hotels near East End Seaport Maritime Museum
- Hotels near Greenport Farmers' Market
- Hotels near Railroad Museum of Long Island
- B&B in Greenport Station
- Vacation Homes in Greenport Station
- Silver Beach Hotels
- Hotels near Osprey's Dominion
- Hotels near The Old Field Vineyards
- 4 Star Hotels in Peconic
- Beach Resorts & in Peconic
- Cheap Hotels in Peconic
- Hotels with Pool in Peconic
- Waterpark Hotels & Resorts in Peconic
- Peconic Hotels
- Houseboats in Peconic
- Hotels near Greenport Carousel
- B&B in Greenport
- Beach Resorts & in Greenport
- Boutique Hotels in Greenport
- Gay Friendly Hotels in Greenport
- Historic Hotels in Greenport
- Hotels with Pool in Greenport
- Hotels with Free Parking in Greenport
- Pet Friendly Hotels in Greenport
- Spa Resorts & in Greenport
- Hotels with a Wedding Venue in Greenport
- Winery Hotels in Greenport
- Greenport Hotels
- Houseboats in Greenport
- Motels in Greenport
- Vacation Homes in Greenport
- Villas in Greenport
- Cottages in Shelter Island Heights
- Kid Friendly Hotels in Shelter Island Heights
- Hotels with Pool in Shelter Island Heights
- Hotels with Bar in Shelter Island Heights
- Hotels with a Gym in Shelter Island Heights
- Hotels with Hot Tubs in Shelter Island Heights
- Winery Hotels in Shelter Island Heights
- Shelter Island Heights Hotels
- Houseboats in Shelter Island Heights
- Resorts in Shelter Island Heights
- 2 Star Hotels in Greenport West
- Hotels with Pool in Greenport West
- Pet Friendly Hotels in Greenport West
- Shelter Island Hotels
- Hotels near Camera Obscura
- Hotels near Sparkling Pointe
- Hotels near Bedell Cellars
- Hotels near Sunset Beach
- Longhouse Reserve
- Peconic Bay Winery
- South Fork Natural History Museum and Nature Center
- Victoria's Secret
- Riverhead Vacations
- Kaplan Meadows Sanctuary
- Suffolk Theater
- Mattebella Vineyards
- Southampton Vacations
- Sagaponack Vacations
- Shinnecock Nation Cultural Center and Museum
- Wolffer Estates Vineyard
- Meschutt Beach
- Railroad Museum of Long Island
- East Hampton Vacations
- Baiting Hollow Hummingbird Sanctuary
- Sag Harbor Vacations
- Shinnecock Hills Golf Course
- Duck Walk Vineyards
- Orient Vacations
- Kontokosta Winery
- Hampton Bays Vacations
- East Hampton Main Beach
- Flanders Vacations
- Pugliese Vineyards
- Shelter Island Vacations
- Sparkling Pointe
- Amelia Cottage Museum
- Hamptons Vacations
- Channing Daughters Winery
