Deals on vacations and trips to Cheshire
Save when you book Cheshire package deals
Cheshire flight + hotel vacation packages
Price found within the past 48 hours. Click for updated prices.
New Haven Hotel
Downtown New Haven
Price was $552, price is now $427 per person
$427
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Jacksonville (JAX) to New Haven (HVN)
A gym, self parking, and laundry facilities are featured at this hotel. WiFi in public areas is free. Traveling on business? Take advantage of the 2 conference rooms, along with dry cleaning/laundry services.
Landing Apartments New Haven Near Dixwell
Newhallville
Save 100% on your flight
Price was $911, price is now $710 per person
$710
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Jacksonville (JAX) to New Haven (HVN)
This apartment includes free WiFi in public areas and a virtual front desk.
Landing Furnished Apartments near YSM
Downtown New Haven
Price was $713, price is now $579 per person
$579
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Jacksonville (JAX) to New Haven (HVN)
A gym is featured at this apartment, along with free WiFi in public areas and a virtual front desk.
Landing Furnished Apartment Near Yale University
Downtown New Haven
Price was $638, price is now $518 per person
$518
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Jacksonville (JAX) to New Haven (HVN)
A gym is featured at this apartment, along with free WiFi in public areas and laundry facilities. A virtual front desk are provided for your convenience.
Luxury Furnished Apartments by Hyatus Downtown at Yale
The Hill
Price was $1,461, price is now $1,189 per person
$1,189
per person
Aug 20 - Aug 23
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
This aparthotel features a gym and a rooftop terrace. Guests will appreciate free perks like free self parking and WiFi in public areas. A garden, express check-out, and dry cleaning are also on offer.
Top Cheshire hotels deals
Cheshire Welcome Inn
1106 S Main St. Cheshire CT
Free Cancellation
Reserve now, pay when you stay
$99 nightly
The price is $114 total per night
$114 total
Jul 1 - Jul 2
Total with taxes and fees
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. The front desk is staffed around-the-clock and laundry facilities are on offer.
Parking included
Free WiFi
New Haven Hotel
229 George Street New Haven CT
Free Cancellation
Reserve now, pay when you stay
$106 nightly
The price is $121 total per night
$121 total
Jul 6 - Jul 7
Total with taxes and fees
A gym, self parking, and laundry facilities are featured at this hotel. WiFi in public areas is free. Traveling on business? Take advantage of the 2 conference rooms, along with dry cleaning/laundry services.
Pet friendly
Free WiFi
Motel 6 Wethersfield, CT - Hartford
1341 Silas Deane Hwy Wethersfield CT
Free Cancellation
Reserve now, pay when you stay
$74 nightly
The price is $85 total per night
$85 total
Jul 1 - Jul 2
Total with taxes and fees
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. The front desk is staffed around-the-clock and laundry facilities are on offer.
Pet friendly
Parking included
Best Western Executive Hotel Of New Haven - West Haven
490 Saw Mill Rd West Haven CT
Free Cancellation
Reserve now, pay when you stay
$103 nightly
The price is $119 total per night
$119 total
Jun 28 - Jun 29
Total with taxes and fees
This hotel features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like full breakfast and free self parking.
Pool
Breakfast included
Hilton Garden Inn Milford
291 Old Gate Lane Milford CT
Free Cancellation
Reserve now, pay when you stay
$115 nightly
The price is $132 total per night
$132 total
Jun 28 - Jun 29
Total with taxes and fees
This hotel features a restaurant, an indoor pool, and a bar/lounge. Enjoy the 24-hour gym and perks like free self parking and free WiFi. A 24-hour business center, a lobby fireplace, and express check-out are also on offer.
Pool
Pet friendly
Omni New Haven Hotel at Yale
155 Temple St New Haven CT
Free Cancellation
Reserve now, pay when you stay
$142 nightly
The price is $163 total per night
$163 total
Jul 23 - Jul 24
Total with taxes and fees
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Self parking, a coffee shop, and limo/town car service are also offered.
Pet friendly
Free WiFi
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Popular places to visit
Roaring Brook Park
Explore the great outdoors at Roaring Brook Park, a lovely green space in Cheshire. Experience the area's entertainment venues and theater scene.
Cheshire Golf Course
Enjoy a round of golf in Cheshire at Cheshire Golf Course. Experience the entertainment venues and theater scene in this romantic area.
Maplecroft Plaza Shopping Center
You can search for that perfect souvenir at Maplecroft Plaza Shopping Center during your visit to Cheshire. Experience the area's entertainment venues and theater scene.
Frequently asked questions
Photos of local treasures
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