Cheshire Vacation Packages

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Your Cheshire Vacation

There's plenty to love about Cheshire, from its rich history to its spectacular views and beyond. When you're ready to say hello to this lively city, our Cheshire vacation packages will be just the ticket. Any trip to Cheshire needs a well-crafted itinerary. Fill yours with leading attractions like Toyota Oakdale Theatre, Choate Rosemary Hall and Mount Southington Ski Area. Expedia will help you escape your daily routine. Tailor your vacation to Cheshire to suit your style of travel, whatever that may look like.

Top Cheshire Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Cheshire Welcome Inn

Cheshire Welcome Inn

2.5 out of 5
Price was CA $1,033, price is now CA $947 per person
CA $947
per person
Jan 1 - Jan 4
found 24 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to New Haven (HVN)
8.4/10 Very good! (895 reviews)
This inn has a lot of potential but unfortunately it was extremely dirty. The room smelled so bad that I could hardly breathe and there was a thick layer of dirt on the walls and baseboards. The bed made a loud creaking noise with any subtle move. I felt so dirty when I left there. We were supposed to leave at 10am and I made my husband get up and drive home at 6am because I couldn't stand to be there any longer. I should have done more research about the property before I stayed but I used to live in Cheshire and it is such a nice town that it really just didn't cross my mind that a place so dirty would be there. The lady who checked me in was very nice and friendly but besides that I have nothing positive to say about my stay.

Reviewed on Nov 13, 2026

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
North End
Price was CA $2,068, price is now CA $1,588 per person
CA $1,588
per person
Dec 20 - Dec 23
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New Haven (HVN)
No reviews

Water's Edge Resort & Spa

Water's Edge Resort & Spa

3.5 out of 5
Westbrook Center
Price was CA $1,276, price is now CA $1,095 per person
CA $1,095
per person
Jan 1 - Jan 4
found 24 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to New Haven (HVN)
8.8/10 Excellent! (1,000 reviews)

Graduate by Hilton New Haven

Graduate by Hilton New Haven

4 out of 5
Downtown New Haven
Price was CA $1,256, price is now CA $1,101 per person
CA $1,101
per person
Jan 1 - Jan 4
found 24 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to New Haven (HVN)
9.2/10 Wonderful! (1,002 reviews)

Landing Apartments New Haven Near Dixwell

Landing Apartments New Haven Near Dixwell

3 out of 5
Newhallville
Price was CA $1,368, price is now CA $1,263 per person
CA $1,263
per person
Dec 24 - Dec 26
found 24 hours ago
Roundtrip non-stop flight included
Halifax (YHZ) to New Haven (HVN)
2/10 (1 review)
The parking situation is very unclear. There is a small sign far from the lot that warns of towing but nothing in the area where you park. No significant warnings in communications with host.

Reviewed on May 25, 2026

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Cheshire Hotel Deals

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 CA $117 per night from Nov 18 to Nov 19
CA $117
CA $135 total
Nov 18 - Nov 19
includes taxes & fees
8.4/10 Very good! (909 reviews)
"This inn has a lot of potential but unfortunately it was extremely dirty. The room smelled so bad that I could hardly breathe and there was a thick layer of dirt on the walls and baseboards. The bed made a loud creaking noise with any subtle move. I felt so dirty when I left there. We were supposed ..."

Reviewed on Nov 13, 2026

Cheshire 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 CA $134 per night from Dec 15 to Dec 16
CA $134
CA $155 total
Dec 15 - Dec 16
includes taxes & fees
The 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 CA $174 per night from Nov 25 to Nov 26
CA $174
CA $200 total
Nov 25 - Nov 26
includes taxes & fees
New Haven Hotel
See all 1,299 properties in Cheshire
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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Stay near popular Cheshire attractions

Roaring Brook Park

8.4/10 (12 reviews)
Explore the great outdoors at Roaring Brook Park, a lovely green space in Cheshire. Experience the area's entertainment venues and theater scene.
See properties

Frequently asked questions

How much does a Cheshire vacation package cost?
You'll find cheap prices from CA $947 on Expedia for your Cheshire break. However, a range of factors like your choice of hotel, the season and length of stay will determine how much your vacation to Cheshire costs.
What are the cheapest months to go to Cheshire?
If you're looking to book a cheap Cheshire vacation package, consider visiting in December, January and February. You'll typically find lower rates on airfares and hotels during these quieter months — ideal for budget-conscious travellers.
How many days is enough for Cheshire?
We'd recommend booking a Cheshire vacation for at least 2 days. This gives you plenty of time to tick off popular sights such as Mount Carmel and Mount Southington Ski Area, as well as explore neighbourhoods like Milldale and Cheshire Historic District. You might even be able to slot in a day trip or two outside of Cheshire.
Is it worth booking a vacation package to Cheshire?
From top attractions such as Cheshire Golf Course and Cheshire Hollow Farm to its excellent hiking, a Cheshire vacation is sure to exceed your expectations. With so much to see and do, it's time to find out for yourself why Cheshire is such a good vacation destination.
How to find the best Cheshire package deals?
Landing a cheap Cheshire package deal is a breeze with Expedia. After you've entered your preferred dates and destination under our "Packages" tab, set your maximum budget, apply a couple of filters and browse what's available. You can personalize your search by "Property class," "Number of bedrooms," "Traveller experience" and more. Sort the results by "Price: low to high" to view the most wallet-friendly Cheshire package deals. Want a simple trick to get the biggest savings? Be flexible with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book a Cheshire vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your hotel, flight and car rental into one great-value price and enjoy significant savings. You'll usually get a better deal than booking each component separately. And you'll still get the flexibility to create a customized Cheshire vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Cheshire?
Land amazing discounts by booking your flights in advance with Expedia. If spontaneity is more your thing, take advantage of our last-minute deals for an impromptu Cheshire getaway.
How to plan a trip to Cheshire?

  1. Pick your dates: The things you plan to do in Cheshire and your preferred season will help you decide when to travel.
  2. Set a budget: Factor in expenses such as flights, transportation and food when calculating how much to save for your trip to Cheshire. Then, pick a hotel that works with your budget, whether that's an economical option or a more luxurious getaway.
  3. Set the duration of your trip: Start by compiling a list of the attractions you'd like to experience in Cheshire. Then, estimate how long you'll need for each, including any travel time.
  4. Combine your flights and hotel: Awesome destination, check. Length of stay, check. All that's left now is to pick a Cheshire vacation package that brings all your bookings together.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.