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.
Quality Suites Stratford

Quality Suites Stratford

2.5 out of 5
Price was CA $602, price is now CA $592 per person
CA $592
per person
Dec 11 - Dec 13
found 19 hours ago
Roundtrip non-stop flight included
Montreal (YUL) to New Haven (HVN)
8.2/10 Very good! (1,000 reviews)
I had a pleasant stay. Breakfast was decent and fully stocked.Beds are very comfortable here and the rooms are well maintained. The walls are thin between rooms. I heard my neighbor snoring as if we were in the same room. My husband snores so it didn’t keep me awake. But that is my only negative feedback. I would stay here again.

Reviewed on Oct 25, 2026

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
North End
Price was CA $2,608, price is now CA $2,269 per person
CA $2,269
per person
Dec 30 - Jan 3
found 2 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to New Haven (HVN)
No reviews

The Surfside Hotel

The Surfside Hotel

2 out of 5
Lordship
Price was CA $934, price is now CA $886 per person
CA $886
per person
Dec 20 - Dec 24
found 16 hours ago
Roundtrip flight included
Toronto (YYZ) to New Haven (HVN)
9.2/10 Wonderful! (227 reviews)

Ready to book your vacation to Cheshire?

 

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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 $125 per night from Nov 19 to Nov 20
CA $125
CA $144 total
Nov 19 - Nov 20
includes taxes & fees
8.4/10 Very good! (897 reviews)
"Quaint roadside motel"

Reviewed on Oct 25, 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 $127 per night from Nov 1 to Nov 2
CA $127
CA $146 total
Nov 1 - Nov 2
includes taxes & fees
7.2/10 Good! (1,611 reviews)
"When we checked in, the guy at the desk wasnt too talkative and just kindof seemed like we were a nuisance. We asked a few times about parking and he somewhat shrugged and told us to go on the ramp and it was underground. We figured it out but it took us a few minutes. The underground garage was ..."

Reviewed on Oct 27, 2026

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 $181 per night from Nov 22 to Nov 23
CA $181
CA $208 total
Nov 22 - Nov 23
includes taxes & fees
9.2/10 Wonderful! (2,401 reviews)
"The staff was helpful and professional. Hotel is well maintained and the room was clean and comfortable"

Reviewed on Oct 28, 2026

New Haven Hotel
See all 1,331 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 $592 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.