Search Deals onChester Vacation Packages
Chester Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.

Hamden Hotel and Suites – Hamden New Haven
Price was $397, price is now $329 per person
$329
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 hotel in Hamden. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast in our reviews. Popular attractions Cinemark North Haven and People's United Center are located nearby.
The staff went above and beyond made sure I was well accommodated. Breakfast was okay it was eatable: I will definitely go back. Cleaning and kitchen staff especially Luz was so welcoming and sweet. She made me feel welcome and at home.
Reviewed on Sep 2, 2026

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 $1,263, price is now $891 per person
$891
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 20 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.
Stayed on a Friday night. We couldn't sleep, the commission and the noise from outside drunk young people’s party goers was making it impossible. They’re lunatics, screaming, fighting, and vandalizing. It’s a disaster. NHP should really clean the streets. One of the main reasons for us to reconsider Yale.
Reviewed on Sep 4, 2026

Landing Furnished Apartment Near Yale University
Price was $805, price is now $645 per person
$645
per person
Oct 22 - Oct 26
found 20 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 23 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

Omni New Haven Hotel at Yale
Price was $679, price is now $558 per person
$558
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.
Chester Vacation Packages 3-4 Night Stays
Price found within the past 48 hours. Click for updated prices.



Chester 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, Dec 25 - Thu, Dec 31
FLL
Fort Lauderdale - Hollywood Intl.
HVN
Tweed - New Haven Regional
$251 Roundtrip, found 4 hours ago
$251
Roundtrip
found 4 hours ago

Wed, Sep 9 - Fri, Sep 11
MYR
Myrtle Beach Intl.
HVN
Tweed - New Haven Regional
$260 Roundtrip, found 9 hours ago
$260
Roundtrip
found 9 hours ago

Sun, Oct 4 - Wed, Oct 7
TTN
Mercer
HVN
Tweed - New Haven Regional
$740 Roundtrip, just found
$740
Roundtrip
just found

Mon, Sep 7 - Thu, Sep 10
GSP
Greenville-Spartanburg Intl.
HVN
Tweed - New Haven Regional
$897 Roundtrip, found 2 days ago
$897
Roundtrip
found 2 days ago
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