Search Deals onSouth Windsor Vacation Packages
South Windsor Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Landing Furnished Apartment Near Yale University
Price was $881, price is now $708 per person
$708
per person
Oct 28 - Nov 1
found 13 hours ago
Roundtrip flight included
Tampa (TPA) to New Haven (HVN)
Stay at this apartment in New Haven. Enjoy free WiFi, a fitness center, and laundry facilities. Popular attractions Schubert Performing Arts Center and Shubert Theater are located nearby.
Was unable to enter the unit as the key was not available in the Lockbox. Landing (the rental company) was unable to locate the key, which was apparently with the cleaning staff, who were unavailable. We ended up having to rent another property for our visit.
Reviewed on Jun 2, 2026
Head of Pond House
Save 100% on your flight
Price was $2,030, price is now $1,416 per person
$1,416
per person
Oct 14 - Oct 21
found 1 day ago
Roundtrip flight included
Dallas (DFW) to New Haven (HVN)
Book a stay at this business-friendly B&B in Water Mill. Enjoy free breakfast, free WiFi, and free parking. Popular attractions The Hamptons Beaches and Cooper's Beach are located nearby.
Amazing hidden B&B gem in Watermill NY! Fantastic property. Beautiful home and property! Will definitely be back!
Reviewed on Aug 23, 2026
Hyatus Luxury Residences City Crossing
Save 100% on your flight
Price was $1,804, price is now $1,329 per person
$1,329
per person
Nov 24 - Dec 1
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
Book a stay at this business-friendly aparthotel in New Haven. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Knights of Columbus Museum and Shubert Theater are located nearby.
The room was spacious and clean. Close to new haven union station, yale university and downtown. We enjoyed the pool, gym and the rooftop. Check in and check out process were very smooth. Sarah was very responsive to our questions. Would def stay here again.
Reviewed on Aug 10, 2026
Landing Apartments New Haven Near Dixwell
Save 100% on your flight
Price was $1,122, price is now $832 per person
$832
per person
Nov 26 - Dec 1
found 22 hours ago
Roundtrip non-stop flight included
Dallas (DFW) to New Haven (HVN)
Stay at this apartment in New Haven. Enjoy an in-room coffeemaker and air conditioning. Popular attractions Payne Whitney Gymnasium and Peabody Museum of Natural History are located nearby.
The parking situation is very unclear. There is a small sign far from the lot that warns of towing but nothing in the area where you park. No significant warnings in communications with host.
Reviewed on May 25, 2026
New Haven Hotel
Price was $1,095, price is now $813 per person
$813
per person
Nov 24 - Dec 1
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
Book a stay at this business-friendly hotel in New Haven. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff and the convenient parking in our reviews. Popular attractions Shubert Theater and Schubert Performing Arts Center are located nearby.
Graduate by Hilton New Haven
Price was $1,014, price is now $797 per person
$797
per person
Nov 24 - Dec 1
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
Stay at this hotel in New Haven. Enjoy free WiFi, breakfast (surcharge), and free bicycles on site. Our guests praise the helpful staff and the comfy rooms in our reviews. Popular attractions Art Plus Studio and Harkness Tower are located nearby.
Water's Edge Resort & Spa
Price was $981, price is now $778 per person
$778
per person
Nov 26 - Nov 29
found 1 day ago
Roundtrip flight included
Tampa (TPA) to New Haven (HVN)
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 attractions Tanger Outlets and Westbrook Town Beach are located nearby.
Everything is perfect of what we need for short getaway to wind down labor day weekend. Short ride to New York . Thank you Waters edge resort and Spa . Westbrook Ct .
Reviewed on Sep 12, 2026
Hyatt Place Milford / New Haven
Price was $1,000, price is now $796 per person
$796
per person
Nov 24 - Dec 1
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
Book a stay at this business-friendly hotel in Milford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Westfield Connecticut Post Mall and Milford Plaza Shopping Center are located nearby.
We had to ask for a different room. Mold on wall by the AC and smelled bad. The bed was the most uncomfortable bed I have ever slept in and the second room was just as uncomfortable but no mold. Also, the smoke detectors go off when you shower.
Reviewed on Sep 13, 2026
South Windsor Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
South Windsor Vacation Packages 5-7 Night Stays
Price found within the past 48 hours. Click for updated prices.
Top Flight Deals
Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.
Fri, Dec 4 - Sat, Dec 12
MCO
Orlando Intl.
BDL
Bradley Intl.
$82 Roundtrip, found 1 day ago
$82
Roundtrip
found 1 day ago
Thu, Nov 12 - Mon, Nov 16
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$181 Roundtrip, found 11 hours ago
$181
Roundtrip
found 11 hours ago
Fri, Jan 29 - Mon, Feb 1
TPA
Tampa Intl.
BDL
Bradley Intl.
$200 Roundtrip, found 12 hours ago
$200
Roundtrip
found 12 hours ago
Wed, Oct 14 - Mon, Oct 19
SJU
Luis Munoz Marin Intl.
BDL
Bradley Intl.
$225 Roundtrip, found 4 days ago
$225
Roundtrip
found 4 days ago
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