Search Deals on
South Windsor Vacation Packages

Build your package with 2 more options

South Windsor Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
La Quinta Inn & Suites by Wyndham New Haven

La Quinta Inn & Suites by Wyndham New Haven

3 out of 5
Price was $307, price is now $259 per person
$259
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
Stay at this 3-star business-friendly hotel in New Haven. Enjoy free breakfast, free WiFi, and parking (surcharge). Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Long Wharf Theatre and Wooster Square are located nearby.
Hilton Garden Inn Hartford North/Bradley Int'l Airport

Hilton Garden Inn Hartford North/Bradley Int'l Airport

3 out of 5
Price was $538, price is now $405 per person
$405
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip flight included
San Juan (SJU) to New Haven (HVN)
Stay at this 3-star business-friendly hotel in Windsor. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Windsor Arts Center and Northwest Park are located nearby.
Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
Price was $1,947, price is now $1,571 per person
$1,571
per person
Dec 15 - Dec 18
just found
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
Stay at this 5-star luxury vacation home in Bridgeport. Enjoy free WiFi, free parking, and a garden. Popular attractions Svihra Park and Glenwood Park are located nearby.
Cambria Hotel Manchester South Windsor

Cambria Hotel Manchester South Windsor

3 out of 5
Price was $942, price is now $815 per person
$815
per person
Nov 24 - Nov 29
found 1 day ago
Roundtrip non-stop flight included
Atlanta (ATL) to New Haven (HVN)
Stay at this 3-star business-friendly hotel in South Windsor. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Xfinity Theatre and Promenade Shops at Evergreen Walk are located nearby.
Home2 Suites by Hilton East Haven New Haven

Home2 Suites by Hilton East Haven New Haven

3 out of 5
Price was $976, price is now $860 per person
$860
per person
Nov 22 - Nov 26
found 12 hours ago
Roundtrip flight included
San Juan (SJU) to New Haven (HVN)
Stay at this 3-star business-friendly inn in East Haven. Enjoy free breakfast, free WiFi, and free parking. Popular attractions Shoreline Trolley Museum and New Haven Harbor are located nearby.
Homewood Suites by Hilton Stratford

Homewood Suites by Hilton Stratford

3 out of 5
Price was $826, price is now $729 per person
$729
per person
Nov 22 - Nov 26
found 12 hours ago
Roundtrip flight included
San Juan (SJU) to New Haven (HVN)
Stay at this 3-star business-friendly hotel in Stratford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Boothe Memorial Park and Museum and SportsCenter of Connecticut are located nearby.
Simsbury Inn

Simsbury Inn

3.5 out of 5
Price was $1,390, price is now $1,231 per person
$1,231
per person
Dec 23 - Dec 28
found 1 day ago
Roundtrip flight included
San Juan (SJU) to New Haven (HVN)
Stay at this 3.5-star business-friendly hotel in Weatogue. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Rosedale Farms & Vineyards and Stratton Brook State Park are located nearby.
The Blake Hotel

The Blake Hotel

4 out of 5
Price was $543, price is now $483 per person
$483
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
Stay at this 4-star business-friendly hotel in New Haven. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the bar and the helpful staff in our reviews. Popular attractions Shubert Theater and White Space Gallery are located nearby.

South Windsor Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Graduate by Hilton New Haven

Graduate by Hilton New Haven

4 out of 5
Downtown New Haven
Price was $399, price is now $316 per person
$316
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
Hilton Garden Inn Hartford North/Bradley Int'l Airport

Hilton Garden Inn Hartford North/Bradley Int'l Airport

3 out of 5
Price was $538, price is now $405 per person
$405
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip flight included
San Juan (SJU) to New Haven (HVN)
Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
Price was $1,947, price is now $1,571 per person
$1,571
per person
Dec 15 - Dec 18
just found
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
New Haven Hotel

New Haven Hotel

3.5 out of 5
Downtown New Haven
Price was $1,104, price is now $924 per person
$924
per person
Nov 22 - Nov 26
found 12 hours ago
Roundtrip flight included
San Juan (SJU) to New Haven (HVN)

South Windsor Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
La Quinta Inn & Suites by Wyndham New Haven

La Quinta Inn & Suites by Wyndham New Haven

3 out of 5
Long Wharf
Price was $889, price is now $770 per person
$770
per person
Nov 23 - Nov 30
found 23 hours ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
Hilton Garden Inn Hartford North/Bradley Int'l Airport

Hilton Garden Inn Hartford North/Bradley Int'l Airport

3 out of 5
Price was $982, price is now $825 per person
$825
per person
Dec 23 - Dec 28
found 1 day ago
Roundtrip flight included
San Juan (SJU) to New Haven (HVN)
Cambria Hotel Manchester South Windsor

Cambria Hotel Manchester South Windsor

3 out of 5
Price was $1,110, price is now $950 per person
$950
per person
Dec 23 - Dec 28
found 1 day ago
Roundtrip flight included
San Juan (SJU) to New Haven (HVN)
Simsbury Inn

Simsbury Inn

3.5 out of 5
Simsbury Center
Price was $1,390, price is now $1,231 per person
$1,231
per person
Dec 23 - Dec 28
found 1 day ago
Roundtrip flight included
San Juan (SJU) 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
Fri, Nov 7 - Mon, Nov 17
MCO
Orlando Intl.
BDL
Bradley Intl.
$64 Roundtrip, found 4 days ago
$64
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Fri, Nov 7 from Orlando Intl. to Bradley Intl., returning Mon, Nov 17, priced at $64 found 4 days ago
Frontier Airlines
Sat, Nov 15 - Sat, Nov 15
ATL
Hartsfield-Jackson Atlanta Intl.
BDL
Bradley Intl.
$131 Roundtrip, found 4 days ago
$131
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Sat, Nov 15 from Hartsfield-Jackson Atlanta Intl. to Bradley Intl., returning Sat, Nov 15, priced at $131 found 4 days ago
Breeze Airways
Fri, Nov 14 - Mon, Nov 17
TPA
Tampa Intl.
BDL
Bradley Intl.
$137 Roundtrip, found 18 hours ago
$137
Roundtrip
found 18 hours ago
Select Breeze Airways flight, departing Fri, Nov 14 from Tampa Intl. to Bradley Intl., returning Mon, Nov 17, priced at $137 found 18 hours ago
JetBlue Airways
Wed, Nov 5 - Mon, Nov 10
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$159 Roundtrip, found 17 hours ago
$159
Roundtrip
found 17 hours ago
Select JetBlue Airways flight, departing Wed, Nov 5 from Fort Lauderdale - Hollywood Intl. to Bradley Intl., returning Mon, Nov 10, priced at $159 found 17 hours ago