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Windsor Vacation Packages

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Windsor Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
The Surfside Hotel

The Surfside Hotel

2 out of 5
Price was $394, price is now $323 per person
$323
per person
Dec 11 - Dec 14
found 6 hours ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
Book a stay at this beach hotel in Stratford. Enjoy free WiFi, free parking, and a beach locale. Popular attractions Long Beach and Lordship Beach are located nearby.
Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
Price was $1,626, price is now $1,057 per person
$1,057
per person
Dec 11 - Dec 14
found 6 hours ago
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.
Graduate by Hilton New Haven

Graduate by Hilton New Haven

4 out of 5
Price was $660, price is now $495 per person
$495
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to New Haven (HVN)
Stay at this 4-star 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 Harkness Tower and White Space Gallery are located nearby.
Cambria Hotel New Haven University Area

Cambria Hotel New Haven University Area

3 out of 5
Price was $610, price is now $475 per person
$475
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to New Haven (HVN)
Stay at this 3-star business-friendly hotel in New Haven. Enjoy free WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions White Space Gallery and Shubert Theater are located nearby.
New Haven Hotel

New Haven Hotel

3.5 out of 5
Price was $617, price is now $495 per person
$495
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to New Haven (HVN)
Stay at this 3.5-star 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 White Space Gallery are located nearby.
Residence Inn by Marriott Southington

Residence Inn by Marriott Southington

3 out of 5
Price was $480, price is now $387 per person
$387
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to New Haven (HVN)
Stay at this 3-star business-friendly hotel in Southington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions Barnes Museum and Southington Public Library are located nearby.
Holiday Inn Cheshire - Southington by IHG

Holiday Inn Cheshire - Southington by IHG

3 out of 5
Price was $509, price is now $412 per person
$412
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to New Haven (HVN)
Stay at this 3-star business-friendly hotel in Southington. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Panthorn Park and Cheshire Hollow Farm are located nearby.
The Blake Hotel

The Blake Hotel

4 out of 5
Price was $692, price is now $577 per person
$577
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) 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.

Windsor Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

2.5 out of 5
Price was $462, price is now $367 per person
$367
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip non-stop 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 $1,626, price is now $1,057 per person
$1,057
per person
Dec 11 - Dec 14
found 6 hours ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
Graduate by Hilton New Haven

Graduate by Hilton New Haven

4 out of 5
Downtown New Haven
Price was $660, price is now $495 per person
$495
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to New Haven (HVN)
Cambria Hotel New Haven University Area

Cambria Hotel New Haven University Area

3 out of 5
West River
Price was $610, price is now $475 per person
$475
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to New Haven (HVN)

Windsor Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

2.5 out of 5
Price was $643, price is now $529 per person
$529
per person
Dec 24 - Dec 29
found 6 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) 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 $806, price is now $630 per person
$630
per person
Jan 19 - Jan 24
found 24 hours ago
Roundtrip flight included
San Juan (SJU) to New Haven (HVN)
Residence Inn by Marriott Southington

Residence Inn by Marriott Southington

3 out of 5
Price was $678, price is now $553 per person
$553
per person
Dec 24 - Dec 29
found 6 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to New Haven (HVN)
Graduate by Hilton New Haven

Graduate by Hilton New Haven

4 out of 5
Downtown New Haven
Price was $1,121, price is now $932 per person
$932
per person
Dec 7 - Dec 14
found 14 hours ago
Roundtrip non-stop flight included
Tallahassee (TLH) 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
Thu, Dec 25 - Sun, Jan 4
MCO
Orlando Intl.
BDL
Bradley Intl.
$69 Roundtrip, found 4 days ago
$69
Roundtrip
found 4 days ago
Select Frontier Airlines flight, departing Thu, Dec 25 from Orlando Intl. to Bradley Intl., returning Sun, Jan 4, priced at $69 found 4 days ago
Breeze Airways
Fri, Nov 14 - Mon, Nov 17
TPA
Tampa Intl.
BDL
Bradley Intl.
$132 Roundtrip, found 8 hours ago
$132
Roundtrip
found 8 hours ago
Select Breeze Airways flight, departing Fri, Nov 14 from Tampa Intl. to Bradley Intl., returning Mon, Nov 17, priced at $132 found 8 hours ago
Frontier Airlines
Sat, Dec 20 - Thu, Jan 1
SJU
Luis Munoz Marin Intl.
BDL
Bradley Intl.
$136 Roundtrip, found 5 days ago
$136
Roundtrip
found 5 days ago
Select Frontier Airlines flight, departing Sat, Dec 20 from Luis Munoz Marin Intl. to Bradley Intl., returning Thu, Jan 1, priced at $136 found 5 days ago
JetBlue Airways
Wed, Dec 17 - Thu, Jan 1
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$148 Roundtrip, found 6 days ago
$148
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Wed, Dec 17 from Fort Lauderdale - Hollywood Intl. to Bradley Intl., returning Thu, Jan 1, priced at $148 found 6 days ago