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.
Holiday Inn Express Southington, an IHG Hotel

Holiday Inn Express Southington, an IHG Hotel

2.5 out of 5
per person
Aug 2 - Aug 4
found 10 hours ago
Roundtrip non-stop flight included
Houston (IAH) to New Haven (HVN)
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.
Hilton Garden Inn Hartford North/Bradley Int'l Airport

Hilton Garden Inn Hartford North/Bradley Int'l Airport

3 out of 5
per person
Aug 2 - Aug 4
found 10 hours ago
Roundtrip non-stop flight included
Houston (IAH) to New Haven (HVN)
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Enjoy free perks like free self parking and an area shuttle.
Simsbury Inn

Simsbury Inn

3.5 out of 5
Simsbury Center
per person
Aug 2 - Aug 4
found 10 hours ago
Roundtrip non-stop flight included
Houston (IAH) to New Haven (HVN)
This smoke-free hotel includes 3 restaurants, an indoor pool, and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the sauna and free perks like continental breakfast and free self parking.
HYATT house Hartford North/Windsor

HYATT house Hartford North/Windsor

3 out of 5
per person
Aug 2 - Aug 4
found 10 hours ago
Roundtrip non-stop flight included
Houston (IAH) to New Haven (HVN)
This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the gym and free perks like buffet breakfast and free self parking.
Residence Inn by Marriott Hartford/Windsor

Residence Inn by Marriott Hartford/Windsor

3 out of 5
per person
Aug 2 - Aug 4
found 10 hours ago
Roundtrip non-stop flight included
Houston (IAH) to New Haven (HVN)
This hotel features a gym and a seasonal outdoor pool. Traveling on business? Take advantage of the business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and parking.

Top Cheshire hotels deals

Holiday Inn Cheshire - Southington, an IHG Hotel

Holiday Inn Cheshire - Southington, an IHG Hotel

3 out of 5
64 Knotter Dr, Cheshire, CT
Free Cancellation
The price is $130 per night
$130
per night
Jun 30 - Jul 1
This hotel features an indoor pool, a 24-hour gym, and a restaurant. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Relax with a drink at the bar/lounge and enjoy perks like free self parking.
Cheshire Welcome Inn

Cheshire Welcome Inn

2.5 out of 5
1106 S Main St., Cheshire, CT
The price is $79 per night
$79
per night
Jun 25 - Jun 26
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

New Haven Hotel

3.5 out of 5
229 George Street, New Haven, CT
Free Cancellation
Reserve now, pay when you stay
The price is $149 per night
$149
per night
Jun 23 - Jun 24
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
Best Western Hartford Hotel & Suites

Best Western Hartford Hotel & Suites

2.5 out of 5
185 Brainard Rd, Hartford, CT
Free Cancellation
Reserve now, pay when you stay
The price is $88 per night
$88
per night
Jun 30 - Jul 1
This hotel features a gym and a seasonal outdoor pool. There's no skimping on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. A 24-hour business center, a terrace, and a garden are also on offer.
Pool
Breakfast included
Courtyard by Marriott Waterbury Downtown

Courtyard by Marriott Waterbury Downtown

3 out of 5
63 Grand St, Waterbury, CT
Free Cancellation
Reserve now, pay when you stay
The price is $109 per night
$109
per night
Jun 18 - Jun 19
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. WiFi in public areas is free. Self parking, a 24-hour business center, and a coffee shop are also offered.
Hilton Garden Inn Shelton

Hilton Garden Inn Shelton

3 out of 5
25 Old Stratford Rd, Shelton, CT
Free Cancellation
Reserve now, pay when you stay
The price is $110 per night
$110
per night
Jul 1 - Jul 2
This hotel features a restaurant, an indoor 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.
Pool
Pet friendly
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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

Image for Cheshire Hollow Farm

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.

Cheshire Hollow Farm
Image for Cheshire Golf Course

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.

Cheshire Golf Course
Image for Quinnipiac Recreation Area

Quinnipiac Recreation Area

Explore the great outdoors at Quinnipiac Recreation Area, a lovely green space in Cheshire. Experience the entertainment venues and theater scene in this romantic area.

Quinnipiac Recreation Area

Photos of local treasures

Browse Cheshire vacation photos for more inspiration

Photo by Tai Bui
Photo by Tai Bui

Frequently asked questions

How much are vacation packages to Cheshire?
Starting from as little as $418, hotel and flight packages are a fabulous way to make your vacation budget stretch further. Watch out Cheshire — here you come!
How long should my Cheshire vacation be?
Your Cheshire escape can be as short or as long as you’d like it to be, but most people stay roughly 2 nights. In the mood to hop off the beaten path and uncover some lesser-known attractions? Book a few more nights and see a different side of this destination.
Where can I get the best vacation package deals for Cheshire?
Travelocity is here to help you lock in a terrific Cheshire package deal. With 400 air carriers and 1,000,000 properties across the globe, we’re sure you’ll find one that works for you.
Why should I purchase my Cheshire vacation package with Travelocity?
We offer round-the-clock support, high-quality service and a Price Match Guarantee. Travel is all about the journey — and we have alluring destinations for you to journey to all across the globe. Travel with us and make your hip pocket happy.
Can I save money on my Cheshire car rental if I bundle it with a hotel or flight?
With a Cheshire vacation package, you can combine your flight, hotel and car bookings and save a whole lot. If you’re eager to uncover the best of this awesome area, why not check out Times Square? This top attraction is 75 mi from Cheshire. With your own set of wheels, you’ll be there in the blink of an eye.
What is the best time of year to go to Cheshire?
If you’re eager to avoid costly airfares, tourist masses and sold-out hotels, plan your escape outside of May, June and August. The quietest time to visit Cheshire is November, December and January. You’ll find the highest hotel prices in and the most affordable in .
Which airport is best for Cheshire?
Many fly into Bradley Intl. Airport (BDL), 30 mi north of downtown Cheshire. Others prefer Westchester County Airport (HPN) (50 mi away from central Cheshire) or MacArthur Airport (ISP) (50 mi away from central Cheshire).
What is there to do in Cheshire?
Cheshire has plenty of places to explore, such as Cheshire Golf Course and Cheshire Hollow Farm. These two fantastic attractions are on most visitors’ travel schedules.
Where should I stay when visiting Cheshire?
The Holiday Inn Cheshire - Southington, an IHG Hotel is the number one choice of many travelers. Book soon to avoid missing out.