Search Deals onCheshire Vacation Packages
Cheshire Flight + Hotel Packages
Price found within the past 48 hours. Click for updated prices.
Pier Blue Inn Old Saybrook - Essex
Price was $458, price is now $398 per person
$398
per person
Dec 11 - Dec 14
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
Stay at this hotel in Old Saybrook. Enjoy free WiFi, free parking, and a picnic area. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Chalker Beach and Crystal Lake Town Park are located nearby.
Worn furnishings but room was clean and staff was helpful, accommodated my check in after midnight.
Reviewed on Oct 17, 2026
Beechmont - Perfect for Family Retreat!
Price was $1,728, price is now $1,130 per person
$1,130
per person
Nov 20 - Nov 22
found 12 hours ago
Roundtrip non-stop flight included
Fort Lauderdale (FLL) to New Haven (HVN)
Book a stay at this luxury vacation home in Bridgeport. Enjoy free WiFi, free parking, and a garden. Popular attractions Beardsley Zoo and Lafayette Park are located nearby.
Las Flores Villa
Save 100% on your flight
Price was $5,569, price is now $4,122 per person
$4,122
per person
Nov 24 - Nov 27
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
Book a stay at this luxury vacation home in New Preston. Enjoy free WiFi, free parking, and private pools. Popular attractions Hopkins Vineyard and Lake Waramaug are located nearby.
Omni New Haven Hotel at Yale
Price was $547, price is now $462 per person
$462
per person
Dec 11 - Dec 14
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.
Very comfortable beds. Great food and views from the restaurant.
Reviewed on Oct 16, 2026
Landing Apartments New Haven Near Dixwell
Price was $654, price is now $558 per person
$558
per person
Dec 11 - Dec 14
found 2 hours 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 Peabody Museum of Natural History and Grove Street Cemetery 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
Graduate by Hilton New Haven
Price was $605, price is now $526 per person
$526
per person
Dec 11 - Dec 14
found 1 day 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 Harkness Tower and Schubert Performing Arts Center are located nearby.
Hyatus Luxury Residences City Crossing
Price was $728, price is now $639 per person
$639
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 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.
Fast and effective check-in, great amenities in the building. Kitchen well furnished.
Overall great experience.
Reviewed on Oct 11, 2026
Landing Furnished Apartment Near Yale University
Price was $580, price is now $512 per person
$512
per person
Dec 17 - Dec 20
found 1 day 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.
Check in automated, but the key box was broken and it took me 30 on the phone with IT to get the keys. When I entered the apartment a water leak in the city had destroyed a chunk of the ceiling and there was a mess of drywall and dirty water on the floor. The firm tried to relocate me an hour away before promising to clean up and repair the problem while I was out, but maintenance never arrived. We had to book a hotel nearby. These people are incompetent
Reviewed on Sep 14, 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, Nov 13 - Wed, Dec 2
SJU
Luis Munoz Marin Intl.
BDL
Bradley Intl.
$115 Roundtrip, found 11 hours ago
$115
Roundtrip
found 11 hours ago
Thu, Dec 24 - Thu, Jan 7
TPA
Tampa Intl.
HVN
Tweed - New Haven Regional
$169 Roundtrip, found 14 hours ago
$169
Roundtrip
found 14 hours ago
Thu, Nov 12 - Mon, Nov 16
FLL
Fort Lauderdale - Hollywood Intl.
BDL
Bradley Intl.
$174 Roundtrip, found 5 hours ago
$174
Roundtrip
found 5 hours ago
Fri, Nov 13 - Sun, Nov 15
FLL
Fort Lauderdale - Hollywood Intl.
HVN
Tweed - New Haven Regional
$177 Roundtrip, just found
$177
Roundtrip
just found
Discover Other Travel Deals
- Cheshire Hollow Farm Vacations
- Cheshire Golf Course Vacations
- Roaring Brook Park Vacations
- Maplecroft Plaza Shopping Center Vacations
- Barker Character Vacations
- Bartlem Park Vacations
- Drazen Orchards Vacations
- Quinnipiac Recreation Area Vacations
- Yale University Vacations
- PeoplesBank Arena Vacations
- Quinnipiac University Vacations
- Yale-New Haven Hospital Vacations
- Las Vegas Vacations
- Cancun Vacations
- Miami Vacations
- Corona Vacations
- Cabo San Lucas Vacations
- Disneyland Park Vacations
- New York Vacations
- Honolulu Vacations
- Los Angeles Vacations
- Maui Vacations
- Orlando Vacations
- New Orleans Vacations
- Canada Vacations
- Tulum Vacations
- Bali Vacations
- Maldives Vacations
- Clearwater Beach Vacations
- Denver Vacations
- South Beach Vacations
- Key West Vacations
