Search Deals on
Winsted Vacation Packages

Build your package with 2 more options

Winsted 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 $457, price is now $410 per person
$410
per person
Dec 17 - Dec 20
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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.
Clean room

Reviewed on Nov 8, 2026

Hyatus Luxury Residences City Crossing

Hyatus Luxury Residences City Crossing

4 out of 5
Price was $1,168, price is now $980 per person
$980
per person
Dec 24 - Dec 28
just found
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.
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

Graduate by Hilton New Haven

Graduate by Hilton New Haven

4 out of 5
Price was $834, price is now $727 per person
$727
per person
Dec 24 - Dec 28
just found
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.

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
Price was $1,681, price is now $1,497 per person
$1,497
per person
Dec 24 - Dec 27
found 2 hours ago
Roundtrip flight included
Tampa (TPA) 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.

New Haven Hotel

New Haven Hotel

3.5 out of 5
Price was $746, price is now $672 per person
$672
per person
Dec 24 - Dec 28
just found
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 White Space Gallery are located nearby.

Mayflower Motel Milford

Mayflower Motel Milford

2 out of 5
Price was $721, price is now $650 per person
$650
per person
Dec 22 - Dec 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
Stay at this motel in Milford. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff in our reviews. Popular attractions Westfield Connecticut Post Mall and Bowlero Milford are located nearby.

Luxury Furnished Apartments by Hyatus Downtown at Yale

Luxury Furnished Apartments by Hyatus Downtown at Yale

3.5 out of 5
Price was $1,057, price is now $960 per person
$960
per person
Dec 24 - Dec 28
just found
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
Stay at this aparthotel in New Haven. Enjoy free WiFi, free parking, and a rooftop terrace. Popular attractions Shubert Theater and White Space Gallery are located nearby.
Great location if visiting Yale. Felt very safe.

Reviewed on Nov 8, 2026

Winsted 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 $834, price is now $727 per person
$727
per person
Dec 24 - Dec 28
just found
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
Hyatus Luxury Residences City Crossing

Hyatus Luxury Residences City Crossing

4 out of 5
The Hill
Price was $1,168, price is now $980 per person
$980
per person
Dec 24 - Dec 28
just found
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
North End
Price was $1,681, price is now $1,497 per person
$1,497
per person
Dec 24 - Dec 27
found 2 hours ago
Roundtrip flight included
Tampa (TPA) to New Haven (HVN)

Top Flight Deals

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

Breeze Airways
Wed, Dec 2 - Mon, Dec 14
MCO
Orlando Intl.
BDL
Bradley Intl.
$172 Roundtrip, found 2 hours ago
$172
Roundtrip
found 2 hours ago
Select Breeze Airways flight, departing Wed, Dec 2 from Orlando Intl. to Bradley Intl., returning Mon, Dec 14, priced at $172 found 2 hours ago
Breeze Airways
Wed, Jan 27 - Tue, Feb 2
TPA
Tampa Intl.
BDL
Bradley Intl.
$192 Roundtrip, found 10 hours ago
$192
Roundtrip
found 10 hours ago
Select Breeze Airways flight, departing Wed, Jan 27 from Tampa Intl. to Bradley Intl., returning Tue, Feb 2, priced at $192 found 10 hours ago
Bargain Flight
Wed, Jan 13 - Sat, Jan 23
CLT
Charlotte-Douglas Intl.
BDL
Bradley Intl.
$209 Roundtrip, found 20 hours ago
$209
Roundtrip
found 20 hours ago
Select Bargain Flight flight, departing Wed, Jan 13 from Charlotte-Douglas Intl. to Bradley Intl., returning Sat, Jan 23, priced at $209 found 20 hours ago
Frontier Airlines
Wed, Feb 24 - Sat, Feb 27
ATL
Hartsfield-Jackson Atlanta Intl.
BDL
Bradley Intl.
$210 Roundtrip, found 2 hours ago
$210
Roundtrip
found 2 hours ago
Select Frontier Airlines flight, departing Wed, Feb 24 from Hartsfield-Jackson Atlanta Intl. to Bradley Intl., returning Sat, Feb 27, priced at $210 found 2 hours ago