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.
2.0-star property
Hotel MOCA NYC
Manhattan
6.2/10 (1,030 reviews)
Dec 19 - Dec 26
7 night stay
Los Angeles (LAX) to New York (JFK)
American Airlines • Roundtrip • Coach
Price was $3,096, price is now $1,736 per person
$1,736
per person
just found
Good hotel you can take the Bus Bx13 to Yankee Stadium .
Reviewed on Sep 28, 2026
5.0-star property
1 Hotel Brooklyn Bridge
9/10 Wonderful! (1,010 reviews)
Dec 12 - Dec 15
3 night stay
Dallas (DFW) to New York (JFK)
American Airlines • Coach
New York (JFK) to Dallas (DFW)
Frontier Airlines • Coach
Save 100% on your flight
Price was $2,552, price is now $1,527 per person
$1,527
per person
found 1 day ago
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
Reserve now, pay when you stay
15.32 mi from city center
$78 nightly
The price is $90 total per night
$90 total
Oct 6 - Oct 7
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 4 - Oct 5
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
