Search Deals onWinsted Vacation Packages
Winsted Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Heritage Hotel, Golf & Conference Center
Price was $660, price is now $524 per person
$524
per person
Nov 25 - Nov 30
found 23 hours ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
Book a stay at this boutique hotel in Southbury. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Vicinanza Studios & Gallery and Hollow Park are located nearby.
Beechmont - Perfect for Family Retreat!
Save 100% on your flight
Price was $1,617, price is now $929 per person
$929
per person
Nov 6 - Nov 8
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 Beardsley Zoo and Lafayette Park are located nearby.
Landing Apartments New Haven Near Dixwell
Save 100% on your flight
Price was $1,159, price is now $859 per person
$859
per person
Nov 25 - Nov 30
found 22 hours ago
Roundtrip flight included
Orlando (MCO) 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
Hyatus Luxury Residences City Crossing
Save 100% on your flight
Price was $1,377, price is now $1,038 per person
$1,038
per person
Nov 25 - Nov 30
found 21 hours 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
New Haven Hotel
Price was $845, price is now $647 per person
$647
per person
Nov 25 - Nov 30
found 22 hours 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 $759, price is now $615 per person
$615
per person
Nov 25 - Nov 30
found 23 hours 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.
Hyatt Place Milford / New Haven
Price was $837, price is now $687 per person
$687
per person
Nov 25 - Nov 30
found 21 hours 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.
The fire alarm goes off when you take a shower. Seriously. Not acceptable. Hotel is under construction outside and drilling is heard inside. I requested a refund and got the bum’s rush. Buyer beware.
Reviewed on Sep 19, 2026
Best Western Executive Hotel Of New Haven - West Haven
Price was $658, price is now $542 per person
$542
per person
Nov 25 - Nov 30
found 21 hours ago
Roundtrip flight included
Orlando (MCO) 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 Bradley Point Beach are located nearby.
Winsted Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Winsted 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.
Thu, Nov 12 - Thu, Nov 19
MCO
Orlando Intl.
BDL
Bradley Intl.
$155 Roundtrip, found 1 day ago
$155
Roundtrip
found 1 day ago
Mon, Nov 23 - Thu, Nov 26
DCA
Ronald Reagan Washington National
BDL
Bradley Intl.
$177 Roundtrip, found 1 day ago
$177
Roundtrip
found 1 day ago
Thu, Nov 12 - Mon, Nov 16
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$179 Roundtrip, found 1 hour ago
$179
Roundtrip
found 1 hour ago
Fri, Jan 29 - Mon, Feb 1
TPA
Tampa Intl.
BDL
Bradley Intl.
$200 Roundtrip, found 1 day ago
$200
Roundtrip
found 1 day ago
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