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.
Pier Blue Inn Old Saybrook - Essex

Pier Blue Inn Old Saybrook - Essex

2 out of 5
Saybrook Manor
Price was CA $893, price is now CA $741 per person
CA $741
per person
Sep 4 - Sep 7
found 1 day ago
Roundtrip flight included
Toronto (YTO) to New Haven (HVN)
8/10 Very good! (1,001 reviews)
Still the same wonderful little place as the last time I stayed here!

Reviewed on Jul 11, 2026

Hyatus Luxury Residences City Crossing

Hyatus Luxury Residences City Crossing

4 out of 5
The Hill
Price was CA $1,924, price is now CA $1,595 per person
CA $1,595
per person
Aug 13 - Aug 17
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New Haven (HVN)
9.2/10 Wonderful! (31 reviews)
the room and amenities are well maintained, clean and convenient, the customer service is awesome , answering requests fast and responsive.

Reviewed on Jul 5, 2026

Landing Furnished Apartment Near Yale University

Landing Furnished Apartment Near Yale University

3 out of 5
Downtown New Haven
Price was CA $1,123, price is now CA $934 per person
CA $934
per person
Aug 13 - Aug 17
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New Haven (HVN)
2/10 (1 review)
Was unable to enter the unit as the key was not available in the Lockbox. Landing (the rental company) was unable to locate the key, which was apparently with the cleaning staff, who were unavailable. We ended up having to rent another property for our visit.

Reviewed on Jun 2, 2026

Graduate by Hilton New Haven

Graduate by Hilton New Haven

4 out of 5
Downtown New Haven
Price was CA $1,063, price is now CA $902 per person
CA $902
per person
Aug 13 - Aug 17
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New Haven (HVN)
9.2/10 Wonderful! (1,005 reviews)
N/A

Reviewed on Jul 12, 2026

Luxury Furnished Apartments by Hyatus Downtown at Yale

Luxury Furnished Apartments by Hyatus Downtown at Yale

3.5 out of 5
The Hill
Price was CA $1,773, price is now CA $1,627 per person
CA $1,627
per person
Aug 13 - Aug 17
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New Haven (HVN)
9.6/10 Exceptional! (84 reviews)
I had an amazing stay at the Hyatus. The property was exceptionally clean and well maintained, which made me feel comfortable from the moment I arrived. The location was perfect—convenient to everything I needed while still being quiet and peaceful, making it easy to relax after a busy week. Overall, it was a wonderful experience, and I would absolutely stay here again. Highly recommend!

Reviewed on Jul 6, 2026

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 $126 per night from Jul 26 to Jul 27
CA $126
CA $145 total
Jul 26 - Jul 27
includes taxes & fees
8.4/10 Very good! (843 reviews)
"We used the motel to break up our drive to Maine and to see family in the area. Great location with a nice bed for a good night's sleep. Room was dominated by the bed so not much room for anything else. It served it's purpose. Would stay again."

Reviewed on Jul 13, 2026

Cheshire Welcome Inn
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 $183 per night from Jul 26 to Jul 27
CA $183
CA $210 total
Jul 26 - Jul 27
includes taxes & fees
9.2/10 Wonderful! (2,226 reviews)
"The balcony view was good...the breeze and the flying seagulls were a great way to start my morning. Breakfast was available for purchase, but I did not buy anything."

Reviewed on Jul 14, 2026

New Haven 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 $146 per night from Jul 29 to Jul 30
CA $146
CA $168 total
Jul 29 - Jul 30
includes taxes & fees
8/10 Very good! (1,721 reviews)
"Everything was great !! except the internet as my stay included me working from the hotel most the day."

Reviewed on Jul 13, 2026

Best Western Executive Hotel Of New Haven - West Haven
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.
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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 $741 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.