Search Deals onCheshire Vacation Packages
Cheshire Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Omni New Haven Hotel at Yale
Price was $690, price is now $566 per person
$566
per person
Nov 6 - Nov 8
found 1 day 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 Schubert Performing Arts Center and Shubert Theater are located nearby.
Beechmont - Perfect for Family Retreat!
Save 100% on your flight
Price was $1,542, price is now $835 per person
$835
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 Svihra Park and Beardsley Zoo are located nearby.
Head of Pond House
Save 100% on your flight
Price was $1,280, price is now $897 per person
$897
per person
Oct 8 - Oct 11
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
Book a stay at this business-friendly B&B in Water Mill. Enjoy free breakfast, free WiFi, and free parking. Popular attractions The Hamptons Beaches and Cooper's Beach are located nearby.
Amazing hidden B&B gem in Watermill NY! Fantastic property. Beautiful home and property! Will definitely be back!
Reviewed on Aug 23, 2026
Landing Apartments New Haven Near Dixwell
Save 100% on your flight
Price was $952, price is now $745 per person
$745
per person
Nov 6 - Nov 8
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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
New Haven Hotel
Save 100% on your flight
Price was $1,011, price is now $791 per person
$791
per person
Oct 22 - Oct 26
found 14 hours ago
Roundtrip flight included
Atlanta (ATL) 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.
Hyatus Luxury Residences City Crossing
Save 100% on your flight
Price was $1,363, price is now $1,074 per person
$1,074
per person
Nov 13 - Nov 15
found 1 day 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.
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
Landing Furnished Apartment Near Yale University
Price was $805, price is now $645 per person
$645
per person
Oct 22 - Oct 26
found 14 hours ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
Stay at this apartment in New Haven. Enjoy free WiFi, a fitness center, and laundry facilities. Popular attractions Schubert Performing Arts Center and Shubert Theater are located nearby.
Was unable to enter the unit as the key was not available in the Lockbox. Landing (the rental company) was unable to locate the key, which was apparently with the cleaning staff, who were unavailable. We ended up having to rent another property for our visit.
Reviewed on Jun 2, 2026
Graduate by Hilton New Haven
Price was $939, price is now $757 per person
$757
per person
Oct 11 - Oct 16
found 17 hours 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.
It’s the most charming property in New Haven - loved it! Fantastic staff!
Reviewed on Sep 2, 2026
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.
Fri, Oct 2 - Sun, Oct 4
MCO
Orlando Intl.
BDL
Bradley Intl.
$110 Roundtrip, found 3 hours ago
$110
Roundtrip
found 3 hours ago
Thu, Dec 3 - Sun, Dec 6
MCO
Orlando Intl.
HVN
Tweed - New Haven Regional
$148 Roundtrip, found 3 days ago
$148
Roundtrip
found 3 days ago
Wed, Oct 14 - Fri, Oct 23
SJU
Luis Munoz Marin Intl.
BDL
Bradley Intl.
$161 Roundtrip, found 3 hours ago
$161
Roundtrip
found 3 hours ago
Thu, Nov 12 - Mon, Nov 16
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$181 Roundtrip, found 2 hours ago
$181
Roundtrip
found 2 hours ago
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