
Southold Vacation Packages
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Top Southold vacation package deals
Price found within the past 48 hours. Click for updated prices.

3.5-star property
Tanglwood Resort
8.6/10 Excellent! (412 reviews)
Jan 14 - Jan 18
4 night stay
Orlando (MCO) to New York (JFK)
Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $787, price is now $512 per person
$512
per person
found 1 day ago
It was perfect for our trip. Close to the lake and other attractions and near several good restaurants and stores .
Reviewed on Oct 18, 2026


5.0-star property
The Langham, New York, Fifth Avenue
Manhattan
9.6/10 Exceptional! (1,006 reviews)
Jan 14 - Jan 17
3 night stay
Houston (IAH) to New York (JFK)
Delta • Coach
New York (JFK) to Houston (IAH)
JetBlue Airways • Coach
Price was $1,421, price is now $880 per person
$880
per person
found 20 hours ago
Very clean, attentive staff and very helpful
Reviewed on Nov 8, 2026

5.0-star property
1 Hotel Brooklyn Bridge
9/10 Wonderful! (1,004 reviews)
Jan 14 - Jan 17
3 night stay
Houston (IAH) to New York (JFK)
Delta • Coach
New York (JFK) to Houston (IAH)
JetBlue Airways • Coach
Price was $1,578, price is now $998 per person
$998
per person
found 20 hours ago
Incredible views, ambiance, staff, and overall experience! The only thing to note is that it can be quite loud since you're right on the waterfront and the ferries and boats sound their horns frequently
Reviewed on Nov 8, 2026

3.5-star property
Paradise Stream Resort
8/10 Very Good! (1,189 reviews)
Jan 14 - Jan 18
4 night stay
Orlando (MCO) to New York (JFK)
Frontier Airlines • Roundtrip • Coach
Save 100% on your flight
Price was $1,104, price is now $700 per person
$700
per person
found 1 day ago
I was very disappointed. I paid a lot of money for the champagne Tower and I was extremely disappointed the pool area smelled so bad you couldn't even go in it. So that means I didn't get to go swimming I didn't get to use the sauna area besides the handle to the song I wasn't even attached so you couldn't even pull the door closed . There were chunks missing out of the bottom of the floor of the pool. The bathroom door wouldn't close at all to have any privacy. It was a waste of money. And I sure didn't get anything reimbursed it that's for sure.
Reviewed on Nov 9, 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
$210 nightly
The price is $237 total per night
$237 total
Nov 23 - Nov 24
Total with taxes and fees
Guests of The Shoals Suites and Slips enjoy features like a business center, free use of bicycles and express check-out. Helpful staff is there to provide front-desk service during limited hours, as well as offer insight about the area. Additional amenities include a reception hall, a communal living room, and a picnic area.
Free WiFi
Air conditioning

Pier Blue Inn Old Saybrook - Essex
1430 Boston Post Rd Old Saybrook CT
Free Cancellation
15.32 mi from city center
$86 nightly
The price is $99 total per night
$99 total
Dec 1 - Dec 2
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
$202 nightly
The price is $232 total per night
$232 total
Dec 10 - Dec 11
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 concierge services, dry cleaning/laundry, 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.
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