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Windsor Vacation Packages

Build your package with 2 more options

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 $778, price is now $637 per person
$637
per person
Feb 11 - Feb 16
found 12 hours ago
Roundtrip flight included
Seattle (SEA) 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 $1,874, price is now $1,305 per person
$1,305
per person
Feb 12 - Feb 15
found 15 hours 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 Glenwood Park and Beardsley Zoo are located nearby.
Water's Edge Resort & Spa

Water's Edge Resort & Spa

3.5 out of 5
Price was $1,176, price is now $1,056 per person
$1,056
per person
Feb 9 - Feb 14
found 20 hours ago
Roundtrip non-stop flight included
Seattle (SEA) 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.

Windsor Vacation Packages 3-4 Night Stays

Price found within the past 48 hours. Click for updated prices.
Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
North End
Price was $1,874, price is now $1,305 per person
$1,305
per person
Feb 12 - Feb 15
found 15 hours ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)

Windsor Vacation Packages 5-7 Night Stays

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

The Surfside Hotel

2 out of 5
Lordship
Price was $778, price is now $637 per person
$637
per person
Feb 11 - Feb 16
found 12 hours ago
Roundtrip flight included
Seattle (SEA) to New Haven (HVN)
Water's Edge Resort & Spa

Water's Edge Resort & Spa

3.5 out of 5
Westbrook Center
Price was $1,176, price is now $1,056 per person
$1,056
per person
Feb 9 - Feb 14
found 20 hours ago
Roundtrip non-stop flight included
Seattle (SEA) 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
Wed, Mar 4 - Mon, Mar 9
MCO
Orlando Intl.
BDL
Bradley Intl.
$68 Roundtrip, just found
$68
Roundtrip
just found
Select Frontier Airlines flight, departing Wed, Mar 4 from Orlando Intl. to Bradley Intl., returning Mon, Mar 9, priced at $68 just found
JetBlue Airways
Wed, Jan 21 - Fri, Jan 23
TPA
Tampa Intl.
BDL
Bradley Intl.
$128 Roundtrip, found 6 days ago
$128
Roundtrip
found 6 days ago
Select JetBlue Airways flight, departing Wed, Jan 21 from Tampa Intl. to Bradley Intl., returning Fri, Jan 23, priced at $128 found 6 days ago
JetBlue Airways
Thu, Mar 5 - Mon, Mar 9
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$139 Roundtrip, just found
$139
Roundtrip
just found
Select JetBlue Airways flight, departing Thu, Mar 5 from Fort Lauderdale - Hollywood Intl. to Bradley Intl., returning Mon, Mar 9, priced at $139 just found
Frontier Airlines
Sat, Jan 24 - Sat, Jan 31
ORD
O'Hare Intl.
BDL
Bradley Intl.
$154 Roundtrip, found 1 day ago
$154
Roundtrip
found 1 day ago
Select Frontier Airlines flight, departing Sat, Jan 24 from O'Hare Intl. to Bradley Intl., returning Sat, Jan 31, priced at $154 found 1 day ago