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.
Motel 6 Southington, CT - Hartford

Motel 6 Southington, CT - Hartford

2 out of 5
Price was CA $1,030, price is now CA $929 per person
CA $929
per person
Sep 25 - Oct 1
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to New Haven (HVN)
6.2/10 (1,002 reviews)
The room i was in had an adjacent door to another room. They people in other room were loud and noisy at 1:30am. There should be a way to sound proof door when both rooms are occupied

Reviewed on Jul. 15, 2025

Hilton Garden Inn Hartford North/Bradley Int'l Airport

Hilton Garden Inn Hartford North/Bradley Int'l Airport

3 out of 5
Price was CA $1,499, price is now CA $1,191 per person
CA $1,191
per person
Sep 25 - Oct 1
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to New Haven (HVN)
8.8/10 Excellent! (1,004 reviews)
It would’ve been better that you had posted that the pool was closed since 2020. My Wife wasn’t too happy about that.

Reviewed on Aug. 18, 2025

Comfort Inn & Suites East Hartford - Hartford

Comfort Inn & Suites East Hartford - Hartford

2.5 out of 5
Price was CA $1,394, price is now CA $1,218 per person
CA $1,218
per person
Sep 25 - Oct 1
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to New Haven (HVN)
7.6/10 Good! (1,001 reviews)
Staff friendly and helpful, great breakfast option

Reviewed on Aug. 16, 2025

Residence Inn by Marriott Southington

Residence Inn by Marriott Southington

3 out of 5
Price was CA $1,398, price is now CA $1,236 per person
CA $1,236
per person
Sep 25 - Oct 1
found 1 day ago
Roundtrip flight included
Vancouver (YVR) to New Haven (HVN)
8.6/10 Excellent! (557 reviews)
Room was excellent. Easy check in. No sugar with the coffee maker. Traffic is noisy all night long.

Reviewed on Aug. 17, 2025

Ready to book your vacation to Cheshire?

 

Choose your dates

Cheshire Hotel Deals

Cheshire Welcome Inn

Cheshire Welcome Inn

2.5 out of 5
1106 S Main St., Cheshire, CT
The price is CA $136 per night from Aug 24 to Aug 25
CA $136
CA $156 total
Aug 24 - Aug 25
includes taxes & fees
8.4/10 Very Good! (716 reviews)
"Comfortable, clean and convenient"

Reviewed on Aug. 7, 2025

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 $117 per night from Aug 24 to Aug 25
CA $117
CA $134 total
Aug 24 - Aug 25
includes taxes & fees
7.6/10 Good! (1,018 reviews)
"Good location. Close to train station and downtown. Also across from the train station and across from Bushnell Park"

Reviewed on Aug. 18, 2025

The Capitol Hotel
Best Western Executive Hotel Of New Haven - West Haven

Best Western Executive Hotel Of New Haven - West Haven

2.5 out of 5
490 Saw Mill Rd, West Haven, CT
Fully refundableReserve now, pay when you stay
The price is CA $145 per night from Aug 24 to Aug 25
CA $145
CA $167 total
Aug 24 - Aug 25
includes taxes & fees
7.8/10 Good! (1,285 reviews)
"Great location with multiple food options nearby."

Reviewed on Aug. 18, 2025

Best Western Executive Hotel Of New Haven - West Haven
See all 1,147 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Cheshire vacation package cost?
You'll find cheap prices from CA $929 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.

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