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

CA $770
per person
Oct 29 - Nov 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New Haven (HVN)
8.2/10 Very good! (1,011 reviews)
Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

North End
Save 100% on your flight
CA $1,397
per person
Dec 4 - Dec 6
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New Haven (HVN)
No reviews
The Surfside Hotel

The Surfside Hotel

Lordship
CA $943
per person
Oct 29 - Nov 1
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New Haven (HVN)
9.2/10 Wonderful! (219 reviews)
Beautiful ocean front location. Private Sandy Beach. Clean and well maintained. Great onsite pub and restaurant. We enjoyed our stay so much!

Reviewed on Sep 16, 2026

Ready to book your vacation to Cheshire?

Choose your dates

Cheshire Hotel Deals

Cheshire Welcome Inn

Cheshire Welcome Inn

1106 S Main St. Cheshire CT
Fully refundableReserve now, pay when you stay
CA $126
CA $144 total
Sep 28 - Sep 29
includes taxes & fees
8.4/10 Very good! (880 reviews)
"Room needs tlc. Bed was broken and shower had no hot water."

Reviewed on Sep 20, 2026

Cheshire Welcome Inn
The Capitol Hotel

The Capitol Hotel

440 Asylum St Hartford CT
Fully refundableReserve now, pay when you stay
CA $143
CA $164 total
Sep 27 - Sep 28
includes taxes & fees
7.4/10 Good! (1,541 reviews)
"Couldn't even visit. Wanted to get a refund to book for another date. I booked the hotel for my aunt's funeral but it got pushed forward. The staff and manager had no sympathy and refused to give me a refund. Almost $300 wasted for nothing."

Reviewed on Sep 24, 2026

The Capitol Hotel
New Haven Hotel

New Haven Hotel

229 George Street New Haven CT
Fully refundableReserve now, pay when you stay
CA $184
CA $212 total
Sep 27 - Sep 28
includes taxes & fees
New Haven Hotel
See all 1,282 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
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Ski Vacations
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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.
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Cheshire Hollow Farm

8.4/10 (15 reviews)
Enjoy a stop at Cheshire Hollow Farm, an entertaining place to visit in Cheshire. Take in the theater scene in this romantic area.
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Barker Character, Comic and Cartoon Museum

7.0/10 (12 reviews)
You can take time to visit Barker Character, Comic and Cartoon Museum during your travels to Cheshire. Experience the entertainment venues and theater scene in this romantic area.
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Maplecroft Plaza Shopping Center

8.6/10 (14 reviews)
You can search for that perfect souvenir at Maplecroft Plaza Shopping Center during your visit to Cheshire. Experience the area's entertainment venues and theater scene.
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Lock 12 Historical Park

Explore the great outdoors at Lock 12 Historical Park, a lovely green space in Cheshire. While in this family-friendly area, you can enjoy the restaurants.
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Drazen Orchards

7.8/10 (10 reviews)
Explore the great outdoors at Drazen Orchards, a lovely green space in Cheshire. Experience the area's entertainment venues and theater scene.
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Bartlem Park

8.6/10 (13 reviews)
Explore the great outdoors at Bartlem Park, a lovely green space in Cheshire. Experience the area's entertainment venues and theater scene.
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Quinnipiac Recreation Area

8.6/10 (14 reviews)
Explore the great outdoors at Quinnipiac Recreation Area, a lovely green space in Cheshire. Experience the entertainment venues and theater scene in this romantic area.
See properties

Frequently asked questions

How much does a Cheshire vacation package cost?
You'll find cheap prices from CA $770 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.

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