Deals on vacations and trips to Cheshire

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Cheshire flight + hotel vacation packages

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Cambria Hotel New Haven University Area

Cambria Hotel New Haven University Area

3 out of 5
West River
per person
Aug 29 - Sep 1
found 23 hours ago
Roundtrip flight included
Tampa (TPA) to New Haven (HVN)
This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the business center and free WiFi in public areas. Self parking, a lobby fireplace, and a computer station are also offered.
Graduate by Hilton New Haven

Graduate by Hilton New Haven

4 out of 5
Downtown New Haven
Save 100% on your flight
per person
Aug 29 - Sep 1
found 23 hours ago
Roundtrip flight included
Tampa (TPA) to New Haven (HVN)
A restaurant and a bar/lounge are featured at this hotel. WiFi in public areas is free. A coffee shop and luggage storage are also provided.
Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

4 out of 5
Downtown New Haven
Save 100% on your flight
per person
Aug 29 - Sep 1
found 23 hours ago
Roundtrip flight included
Tampa (TPA) to New Haven (HVN)
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.
Luxury Apartments by Hyatus at Pierpont

Luxury Apartments by Hyatus at Pierpont

4 out of 5
The Hill
Save 100% on your flight
per person
Aug 29 - Sep 1
found 23 hours ago
Roundtrip flight included
Tampa (TPA) to New Haven (HVN)
This aparthotel features a 24-hour gym and a seasonal outdoor pool. Enjoy the a rooftop terrace and perks like free self parking and a free area shuttle. Free WiFi in public areas, a garden, and a lobby fireplace are also on offer.
Hilton Garden Inn Milford

Hilton Garden Inn Milford

3 out of 5
Save 100% on your flight
per person
Aug 29 - Sep 1
found 23 hours ago
Roundtrip flight included
Tampa (TPA) to New Haven (HVN)
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.

Top Cheshire hotels deals

Cheshire Welcome Inn

Cheshire Welcome Inn

2.5 out of 5
1106 S Main St., Cheshire, CT
Get rates
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
Holiday Inn Cheshire - Southington by IHG

Holiday Inn Cheshire - Southington by IHG

3 out of 5
64 Knotter Dr, Cheshire, CT
Free Cancellation
Get rates
This hotel features an indoor pool, a gym, and a restaurant. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the in-room fitness and perks like free self parking.
Pool
Parking included
The Capitol Hotel

The Capitol Hotel

3 out of 5
440 Asylum St, Hartford, CT
Free Cancellation
Reserve now, pay when you stay
Get rates
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
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
Get rates
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
Hyatt Place Milford / New Haven

Hyatt Place Milford / New Haven

3 out of 5
190 Old Gate Lane, Milford, CT
Free Cancellation
Reserve now, pay when you stay
Get rates
This hotel features a restaurant, a 24-hour gym, and a bar/lounge. 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.
Breakfast included
Pet friendly
La Quinta Inn & Suites by Wyndham New Haven

La Quinta Inn & Suites by Wyndham New Haven

3 out of 5
400 Sargent Dr, New Haven, CT
Free Cancellation
Reserve now, pay when you stay
Get rates
A restaurant and a bar/lounge 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 continental breakfast and free self parking.
Breakfast included
Pet friendly
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See all available properties in Cheshire
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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

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

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.

Barker Character, Comic and Cartoon Museum

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.

Roaring Brook Park

Frequently asked questions

How much are vacation packages to Cheshire?
You'll find an amazing hotel + flight bundle for as little as $269. With one of our Travelocity vacation packages, a stay in Cheshire has never looked more irresistible! Save both time and money and then get a start on packing those bags.
How long should my Cheshire vacation be?
There are no firm rules when it comes to how long you should spend in Cheshire, but most people stay around 3 nights. Got some wiggle room in your departure date? Consider treating yourself to an extra night or two. Then you'll have enough time to check out the area's hidden treasures as well.
Where can I get the best vacation package deals for Cheshire?
For an amazing package deal to Cheshire, nothing compares to Travelocity. Pick from as many as 400 partner airlines and 1,000,000 properties worldwide to create the ultimate escape --- it couldn't be easier than that.
Why should I book my Cheshire vacation bundle with Travelocity?
We offer experiences to suit every type of globetrotter, top-quality service and 24/7 customer support. And to top all that off, we'll match any better price you find with our Price Match Guarantee.
Can I save on my Cheshire car rental if I combine it with a hotel or flight?
With a Cheshire vacation package, you can bundle your car, flight and hotel bookings and save a ton. If you'd love to explore the best of this wonderful location, why not check out Times Square? This popular sight is 75 mi from Cheshire. With your own wheels, you'll be there in the blink of an eye.
Which airport is best for Cheshire?
Many visitors choose to fly into Bradley Intl. Airport (BDL), 30 mi north of downtown Cheshire. Others prefer MacArthur Airport (ISP) (50 mi away from central Cheshire) or Tweed - New Haven Regional Airport (HVN) (17 mi away from central Cheshire).
What is there to do in Cheshire?
Cheshire is overflowing with things to see and do, including Cheshire Golf Course and Cheshire Hollow Farm. These two popular attractions are at the top of most tourists' must-see lists.
Where should I stay when visiting Cheshire?
Many travelers spend their nights at the Holiday Inn Cheshire - Southington, an IHG Hotel. It's a great base for your Cheshire escape.

Photos of local treasures

Browse Cheshire vacation photos for more inspiration

Photo by Tai Bui
Photo by Tai Bui