Cheshire Holiday Packages

Save when you book Cheshire package deals

Book your Cheshire holiday

Wotif is here to help you save your precious moolah.

Roll your hotels and flights into one tidy package.

See more in Cheshire with the extra funds!

You could even see savings of up to . And with more than 550 partner airlines and 665,000 worldwide properties, it's easy to create the getaway of your dreams.

Wotif boasts some of the most attractive deals anywhere online. Better start packing — right now is the time to hit the skies.

Cheshire Accommodation

Time's ticking. We suggest that you don't leave booking accommodation in Cheshire until the last minute. There are only 6 available properties in the surrounding area, so have a peek on Wotif today to score yourself a top deal.

Craving a taste of life's little luxuries? Thinking of treating yourself while you're away? Book a plush room at The Wallingford Victorian Inn (245 N Main St), and you'll feel like a film star. Go on — you've earned it. Alternatively, take a look at the Americas Best Value Inn Cheshire (1106 S Main St). It's a great option if you want a place that's comfy, cosy and easy on the bank balance.

Car Hire in Cheshire

Collecting some wheels right at Bradley International Airport means that you don't need to waste time with transfers or taxis. Payless is just a quick walk from the terminal building.

Searching for a car rental in the centre of town? Enterprise (209 Maple Ave) is the perfect place! Have a wander around and give their staff a shout if you could do with some help.

Holidays to Cheshire

Before you kiss the cat goodbye and jump in that taxi to the airport, it's good to know a couple of things about where you're headed. Keep reading for a few helpful deets about Cheshire.

Want to visualise where you'll be staying? Cheshire is situated 120 kilometres northeast of the city of New York.

With so many cool activities on offer in the area, it's not hard to see why some 29 000 people call this area of Connecticut home.

Top Cheshire hotels

New Haven Hotel

New Haven Hotel

3.5 out of 5
229 George Street, New Haven, CT
Fully refundableReserve now, pay when you stay
The price is NZ$227 per night from 28 Apr to 29 Apr
NZ$227
includes taxes & fees
28 Apr - 29 Apr
Stay at this 3.5-star business-friendly hotel in New Haven. Enjoy free WiFi, a fitness center, and parking (surcharge). Our guests praise the helpful staff and ...
"Staff was friendly. Our stay was everything we expected."

Reviewed on 19 Apr. 2025

New Haven Hotel
Cheshire Welcome Inn

Cheshire Welcome Inn

2.5 out of 5
1106 S Main St., Cheshire, CT
The price is NZ$153 per night from 23 Apr to 24 Apr
NZ$153
includes taxes & fees
23 Apr - 24 Apr
Stay at this motel in Cheshire. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
"Very clean and very kind staff. They went above and beyond. Comfortable beds as well"

Reviewed on 6 Apr. 2025

Cheshire Welcome Inn
Holiday Inn Cheshire - Southington by IHG

Holiday Inn Cheshire - Southington by IHG

3 out of 5
64 Knotter Dr, Cheshire, CT
Fully refundable
The price is NZ$217 per night from 28 Apr to 29 Apr
NZ$217
includes taxes & fees
28 Apr - 29 Apr
Stay at this 3-star business-friendly hotel in Cheshire. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the ...
"Excellent"

Reviewed on 6 Apr. 2025

Holiday Inn Cheshire - Southington by IHG
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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.