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South Windsor Vacation Packages

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South Windsor Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Best Western Executive Hotel Of New Haven - West Haven

Best Western Executive Hotel Of New Haven - West Haven

2.5 out of 5
Price was $551, price is now $476 per person
$476
per person
Dec 17 - Dec 21
found 19 hours ago
Roundtrip flight included
Tampa (TPA) to New Haven (HVN)
Book a stay at this business-friendly hotel in West Haven. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Seabluff Beach and Oak Street Beach are located nearby.
Pretty clean room, staff cleaned my room nicely. Breakfast was okay.

Reviewed on Oct 26, 2026

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
Save 100% on your flight
Price was $1,575, price is now $901 per person
$901
per person
Dec 4 - Dec 6
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
Book a stay at this luxury vacation home in Bridgeport. Enjoy free WiFi, free parking, and a garden. Popular attractions Svihra Park and Beardsley Zoo are located nearby.

Landing Apartments New Haven Near Dixwell

Landing Apartments New Haven Near Dixwell

3 out of 5
Price was $636, price is now $523 per person
$523
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to New Haven (HVN)
Stay at this apartment in New Haven. Enjoy an in-room coffeemaker and air conditioning. Popular attractions Peabody Museum of Natural History and Grove Street Cemetery 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

Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

4 out of 5
Price was $666, price is now $553 per person
$553
per person
Dec 17 - Dec 21
found 24 hours ago
Roundtrip flight included
Tampa (TPA) to New Haven (HVN)
Book a stay at this business-friendly hotel in New Haven. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Shubert Theater and New Haven Green are located nearby.
Please do consider driving to the Pizza places not walking specially at Night.

Reviewed on Oct 28, 2026

Hyatus Luxury Residences City Crossing

Hyatus Luxury Residences City Crossing

4 out of 5
Price was $968, price is now $805 per person
$805
per person
Dec 17 - Dec 21
found 19 hours ago
Roundtrip flight included
Tampa (TPA) 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.
Bed had no mattress cover but was very comfortable. Only one working lamp. Vents could use a good cleaning. I would recommend it and would stay again.

Reviewed on Oct 25, 2026

Landing Furnished Apartment Near Yale University

Landing Furnished Apartment Near Yale University

3 out of 5
Price was $654, price is now $558 per person
$558
per person
Dec 17 - Dec 21
found 19 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 Shubert Theater and White Space Gallery are located nearby.

Graduate by Hilton New Haven

Graduate by Hilton New Haven

4 out of 5
Price was $769, price is now $667 per person
$667
per person
Dec 30 - Jan 2
found 1 day ago
Roundtrip flight included
Fort Lauderdale (FLL) 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.

Hyatt Place Milford / New Haven

Hyatt Place Milford / New Haven

3 out of 5
Price was $604, price is now $531 per person
$531
per person
Dec 17 - Dec 21
found 19 hours ago
Roundtrip flight included
Tampa (TPA) 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.

South Windsor Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Landing Apartments New Haven Near Dixwell

Landing Apartments New Haven Near Dixwell

3 out of 5
Newhallville
Price was $636, price is now $523 per person
$523
per person
Dec 4 - Dec 7
found 1 day ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to New Haven (HVN)
Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
North End
Price was $2,295, price is now $1,353 per person
$1,353
per person
Dec 30 - Jan 2
found 18 hours ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

4 out of 5
Downtown New Haven
Price was $666, price is now $553 per person
$553
per person
Dec 17 - Dec 21
found 24 hours ago
Roundtrip flight included
Tampa (TPA) to New Haven (HVN)
Hyatus Luxury Residences City Crossing

Hyatus Luxury Residences City Crossing

4 out of 5
The Hill
Price was $968, price is now $805 per person
$805
per person
Dec 17 - Dec 21
found 19 hours ago
Roundtrip flight included
Tampa (TPA) to New Haven (HVN)

South Windsor Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Cambria Hotel New Haven University Area

Cambria Hotel New Haven University Area

3 out of 5
West River
Price was $756, price is now $749 per person
$749
per person
Dec 22 - Dec 28
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
Landing Apartments New Haven Near Dixwell

Landing Apartments New Haven Near Dixwell

3 out of 5
Newhallville
Price was $1,282, price is now $1,012 per person
$1,012
per person
Dec 22 - Dec 28
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

4 out of 5
Downtown New Haven
Price was $834, price is now $783 per person
$783
per person
Dec 22 - Dec 28
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)

Top Flight Deals

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Frontier Airlines
Sat, Dec 5 - Sat, Dec 12
MCO
Orlando Intl.
BDL
Bradley Intl.
$164 Roundtrip, found 7 hours ago
$164
Roundtrip
found 7 hours ago
Select Frontier Airlines flight, departing Sat, Dec 5 from Orlando Intl. to Bradley Intl., returning Sat, Dec 12, priced at $164 found 7 hours ago
Breeze Airways
Thu, Nov 12 - Mon, Nov 16
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$167 Roundtrip, found 3 hours ago
$167
Roundtrip
found 3 hours ago
Select Breeze Airways flight, departing Thu, Nov 12 from Fort Lauderdale - Hollywood Intl. to Bradley Intl., returning Mon, Nov 16, priced at $167 found 3 hours ago
American Airlines
Mon, Nov 23 - Thu, Nov 26
DCA
Ronald Reagan Washington National
BDL
Bradley Intl.
$179 Roundtrip, found 8 hours ago
$179
Roundtrip
found 8 hours ago
Select American Airlines flight, departing Mon, Nov 23 from Ronald Reagan Washington National to Bradley Intl., returning Thu, Nov 26, priced at $179 found 8 hours ago
Breeze Airways
Wed, Jan 27 - Mon, Feb 1
TPA
Tampa Intl.
BDL
Bradley Intl.
$197 Roundtrip, just found
$197
Roundtrip
just found
Select Breeze Airways flight, departing Wed, Jan 27 from Tampa Intl. to Bradley Intl., returning Mon, Feb 1, priced at $197 just found