Search Deals onCheshire Vacation Packages
Cheshire Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Mayflower Motel Milford
Price was $542, price is now $489 per person
$489
per person
Dec 20 - Dec 23
found 23 hours 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.
Omni New Haven Hotel at Yale
Price was $886, price is now $726 per person
$726
per person
Jan 3 - Jan 8
found 1 hour ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
Book a stay at this business-friendly hotel in New Haven. Enjoy breakfast (surcharge), room service, and a 24-hour fitness center. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Shubert Theater and New Haven Green are located nearby.
Perfect place to stay when visiting Yale! Just adjacent to the heart of campus and you feel so very well supported!!
Reviewed on Nov 8, 2026
Hyatus Luxury Residences City Crossing
Price was $947, price is now $778 per person
$778
per person
Jan 3 - Jan 8
found 1 hour ago
Roundtrip flight included
Atlanta (ATL) 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
Price was $891, price is now $755 per person
$755
per person
Jan 3 - Jan 8
found 1 hour ago
Roundtrip flight included
Atlanta (ATL) 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.
Best Western Executive Hotel Of New Haven - West Haven
Price was $667, price is now $590 per person
$590
per person
Jan 3 - Jan 8
found 1 hour 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.
Beechmont - Perfect for Family Retreat!
Price was $1,681, price is now $1,497 per person
$1,497
per person
Dec 24 - Dec 27
found 11 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.
Hyatt Place Milford / New Haven
Price was $615, price is now $562 per person
$562
per person
Dec 20 - Dec 23
found 23 hours ago
Roundtrip flight included
Atlanta (ATL) 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.
Cheshire Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.
Cheshire 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, Dec 3 - Mon, Dec 7
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$148 Roundtrip, found 3 hours ago
$148
Roundtrip
found 3 hours ago
Wed, Dec 2 - Mon, Dec 14
MCO
Orlando Intl.
BDL
Bradley Intl.
$172 Roundtrip, found 1 hour ago
$172
Roundtrip
found 1 hour ago
Fri, Dec 11 - Sun, Dec 13
TPA
Tampa Intl.
HVN
Tweed - New Haven Regional
$179 Roundtrip, found 1 day ago
$179
Roundtrip
found 1 day ago
Fri, Dec 25 - Thu, Dec 31
FLL
Fort Lauderdale - Hollywood Intl.
HVN
Tweed - New Haven Regional
$183 Roundtrip, found 2 hours ago
$183
Roundtrip
found 2 hours ago
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