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Winsted Vacation Packages

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Winsted Flight + Hotel Packages

Price found within the past 48 hours. Click for updated prices.
The Best Way Inn

The Best Way Inn

2 out of 5
Price was $362, price is now $302 per person
$302
per person
Nov 20 - Nov 24
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
Stay at this motel in New Haven. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions West Rock Ridge State Park and Yale Golf Course are located nearby.
Luxury Apartments by Hyatus at Pierpont

Luxury Apartments by Hyatus at Pierpont

4 out of 5
Save 100% on your flight
Price was $2,229, price is now $1,619 per person
$1,619
per person
Nov 20 - Nov 24
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
Stay at this 4-star aparthotel in New Haven. Enjoy free WiFi, free parking, and an outdoor pool. Popular attractions Shubert Theater and White Space Gallery are located nearby.
New Haven Hotel

New Haven Hotel

3.5 out of 5
Save 100% on your flight
Price was $1,182, price is now $942 per person
$942
per person
Nov 20 - Nov 24
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
Stay at this 3.5-star business-friendly hotel in New Haven. Enjoy free WiFi, a fitness center, and parking (surcharge). Our guests praise the helpful staff and the convenient parking in our reviews. Popular attractions Shubert Theater and White Space Gallery are located nearby.
Hampton Inn Milford

Hampton Inn Milford

2.5 out of 5
Price was $520, price is now $417 per person
$417
per person
Nov 20 - Nov 24
found 1 day 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 Milford Green and Port Milford are located nearby.
Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
Price was $1,665, price is now $1,341 per person
$1,341
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
Orlando (MCO) 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 New Haven University Area

Cambria Hotel New Haven University Area

3 out of 5
Save 100% on your flight
Price was $1,231, price is now $1,019 per person
$1,019
per person
Nov 20 - Nov 24
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 WiFi, breakfast (surcharge), and a fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Yale University Art Gallery and Yale Repertory Theater are located nearby.
Homewood Suites by Hilton Stratford

Homewood Suites by Hilton Stratford

3 out of 5
Price was $583, price is now $487 per person
$487
per person
Nov 20 - Nov 24
found 1 day ago
Roundtrip flight included
Orlando (MCO) 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.
Red Roof Inn PLUS+ & Suites Guilford

Red Roof Inn PLUS+ & Suites Guilford

2.5 out of 5
Price was $604, price is now $508 per person
$508
per person
Nov 20 - Nov 24
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
Book a stay at this business-friendly hotel in Guilford. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Bill Miller’s Castle and Bishops Orchard and Winery are located nearby.

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 $994, price is now $788 per person
$788
per person
Oct 9 - Oct 12
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
Luxury Apartments by Hyatus at Pierpont

Luxury Apartments by Hyatus at Pierpont

4 out of 5
The Hill
Save 100% on your flight
Price was $2,229, price is now $1,619 per person
$1,619
per person
Nov 20 - Nov 24
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
Luxury Furnished Apartments by Hyatus Downtown at Yale

Luxury Furnished Apartments by Hyatus Downtown at Yale

3.5 out of 5
The Hill
Save 100% on your flight
Price was $1,723, price is now $1,333 per person
$1,333
per person
Nov 20 - Nov 24
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
New Haven Hotel

New Haven Hotel

3.5 out of 5
Downtown New Haven
Save 100% on your flight
Price was $1,182, price is now $942 per person
$942
per person
Nov 20 - Nov 24
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)

Winsted Vacation Packages 5-7 Night Stays

Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Hartford North/Bradley Int'l Airport

Hilton Garden Inn Hartford North/Bradley Int'l Airport

3 out of 5
Price was $745, price is now $597 per person
$597
per person
Oct 28 - Nov 2
found 1 day ago
Roundtrip flight included
San Juan (SJU) to New Haven (HVN)
Courtyard by Marriott Southington

Courtyard by Marriott Southington

3 out of 5
Price was $968, price is now $738 per person
$738
per person
Oct 9 - Oct 14
found 7 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to New Haven (HVN)
Graduate by Hilton New Haven

Graduate by Hilton New Haven

4 out of 5
Downtown New Haven
Price was $1,209, price is now $950 per person
$950
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
Price was $2,671, price is now $2,125 per person
$2,125
per person
Oct 9 - Oct 14
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)

Top Flight Deals

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

Spirit Airlines
Fri, Sep 12 - Mon, Sep 15
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$87 Roundtrip, found 4 days ago
$87
Roundtrip
found 4 days ago
Select Spirit Airlines flight, departing Fri, Sep 12 from Fort Lauderdale - Hollywood Intl. to Bradley Intl., returning Mon, Sep 15, priced at $87 found 4 days ago
Breeze Airways
Fri, Sep 26 - Mon, Sep 29
MCO
Orlando Intl.
BDL
Bradley Intl.
$121 Roundtrip, found 4 days ago
$121
Roundtrip
found 4 days ago
Select Breeze Airways flight, departing Fri, Sep 26 from Orlando Intl. to Bradley Intl., returning Mon, Sep 29, priced at $121 found 4 days ago
JetBlue Airways
Sat, Sep 27 - Wed, Oct 1
TPA
Tampa Intl.
BDL
Bradley Intl.
$127 Roundtrip, found 4 days ago
$127
Roundtrip
found 4 days ago
Select JetBlue Airways flight, departing Sat, Sep 27 from Tampa Intl. to Bradley Intl., returning Wed, Oct 1, priced at $127 found 4 days ago
American Airlines
Tue, Oct 21 - Sat, Oct 25
CLT
Charlotte-Douglas Intl.
BDL
Bradley Intl.
$142 Roundtrip, found 2 days ago
$142
Roundtrip
found 2 days ago
Select American Airlines flight, departing Tue, Oct 21 from Charlotte-Douglas Intl. to Bradley Intl., returning Sat, Oct 25, priced at $142 found 2 days ago