Deals on vacations and trips to Cheshire
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Cheshire flight + hotel vacation packages
Price found within the past 48 hours. Click for updated prices.
Motel 6 Milford, CT
Price was $469, price is now $441 per person
$441
per person
Dec 19 - Dec 22
found 1 day ago
Roundtrip flight included
Raleigh (RDU) to New Haven (HVN)
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. Business travelers can take advantage of the business center. A snack bar/deli, express check-out, and laundry facilities are also on offer.
Hampton Inn Milford
Price was $512, price is now $454 per person
$454
per person
Dec 19 - Dec 22
found 1 day ago
Roundtrip flight included
Raleigh (RDU) to New Haven (HVN)
A restaurant and a gym are featured at this hotel. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like on-the-go breakfast and free self parking.
Madison Beach Hotel
Madison Center
Price was $730, price is now $659 per person
$659
per person
Nov 20 - Nov 22
found 12 hours ago
Roundtrip flight included
Washington (IAD) to New Haven (HVN)
This hotel features a private beach, a full-service spa, and a restaurant. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Enjoy the gym and perks like free WiFi.
Courtyard by Marriott New Haven Orange-Milford
Price was $527, price is now $484 per person
$484
per person
Dec 19 - Dec 22
found 10 hours ago
Roundtrip flight included
Raleigh (RDU) to New Haven (HVN)
This hotel features a restaurant, an outdoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the 24-hour gym and perks like free self parking.
Hyatt Place Uncasville - Casino Area
Price was $500, price is now $473 per person
$473
per person
Nov 20 - Nov 22
found 12 hours ago
Roundtrip flight included
Washington (IAD) to New Haven (HVN)
This hotel features an indoor pool, a 24-hour gym, and a restaurant. Traveling on business? Take advantage of the business center and free WiFi in public areas. Relax with a drink at the bar/lounge and enjoy free perks like buffet breakfast and free self parking.
Top Cheshire hotels deals
Cheshire Welcome Inn
1106 S Main St., Cheshire, CT
$89 nightly
The price is $102 total per night
$102 total
Oct 8 - Oct 9
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
The Capitol Hotel
440 Asylum St, Hartford, CT
Free Cancellation
Reserve now, pay when you stay
$103 nightly
The price is $118 total per night
$118 total
Oct 8 - Oct 9
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free full breakfast and free WiFi. Traveling on business? Take advantage of the 2 conference rooms, business center, and express check-out. Enjoy the 24-hour gym and conveniences like a 24-hour front desk and laundry facilities.
Breakfast included
Pet friendly
Omni New Haven Hotel at Yale
155 Temple St, New Haven, CT
Free Cancellation
Reserve now, pay when you stay
$167 nightly
The price is $192 total per night
$192 total
Oct 21 - Oct 22
Total with taxes and fees
This smoke-free hotel features 2 restaurants, a bar/lounge, and a 24-hour gym. 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
Holiday Inn Express Southington by IHG
120 Laning St, Southington, CT
Free Cancellation
$115 nightly
The price is $132 total per night
$132 total
Nov 2 - Nov 3
Total with taxes and fees
This hotel features a 24-hour gym and a seasonal outdoor pool. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.
Pool
Breakfast 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
$105 nightly
The price is $120 total per night
$120 total
Nov 2 - Nov 3
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
New Haven Hotel
229 George Street, New Haven, CT
$119 nightly
The price is $137 total per night
$137 total
Oct 26 - Oct 27
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
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
Cheshire Hollow Farm
Enjoy a stop at Cheshire Hollow Farm, an entertaining place to visit in Cheshire. Take in the theater scene in this romantic area.
Barker Character, Comic and Cartoon Museum
You can take time to visit Barker Character, Comic and Cartoon Museum during your travels to Cheshire. Experience the entertainment venues and theater scene in this romantic area.
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.
Frequently asked questions
Photos of local treasures
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