Cheshire Holiday Packages

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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

Cheshire Welcome Inn

Cheshire Welcome Inn

2.5 out of 5
1106 S Main St. Cheshire CT
Fully refundableReserve now, pay when you stay
The price is NZ$185 per night from 11 Nov to 12 Nov
NZ$185
11 Nov - 12 Nov
includes taxes & fees
Stay at this motel in Cheshire. Enjoy free Wi-Fi, free parking and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in their reviews. ...
"The only negative I had was that my particular hotel room did not have hot water in the shower only very hot water in the sink. It didn’t matter how long you ran it for. It was a little chilly experience."

Reviewed on 9 Nov 2026

Opens in a new windowCheshire Welcome Inn
The Capitol Hotel

The Capitol Hotel

3 out of 5
440 Asylum St Hartford CT
Fully refundableReserve now, pay when you stay
The price is NZ$200 per night from 17 Nov to 18 Nov
NZ$200
17 Nov - 18 Nov
includes taxes & fees
Stay at this business-friendly hotel in Hartford. Enjoy free breakfast, free Wi-Fi and a 24-hour fitness centre. Our guests praise the breakfast and the helpful ...
"King room wasn’t vacuumed, table tops and bathroom countertops not wiped down, hair in the tub and the shower walls, toilet didn’t completely flush, zero hot water in the morning so showering was not an option, and one of the bath towels looked like it was used to clean up a serious mess and was ..."

Reviewed on 10 Nov 2026

Opens in a new windowThe Capitol Hotel
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$248 per night from 25 Nov to 26 Nov
NZ$248
25 Nov - 26 Nov
includes taxes & fees
Stay at this business-friendly hotel in New Haven. Enjoy free Wi-Fi, breakfast (surcharge) and a fitness centre. Our guests praise the helpful staff and the ...
Opens in a new windowNew Haven Hotel
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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.

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