Cheshire Vacations from $475
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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.
The Latest Cheshire vacation packages
Price found within the past 48 hours. Click for updated prices.
Landing Apartments New Haven Near Dixwell
Newhallville
$584
per person
Dec 18 - Dec 21
found 1 day ago
Roundtrip flight included
Atlanta (ATL) 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
Stay near popular Cheshire attractions
Roaring Brook Park
8.4/10 (12 reviews)
Connecticut's tallest single-drop waterfall cascades dramatically 80 feet through lush woodland. Hike the moderate one-mile loop trail in spring for the most impressive water flow after seasonal rains.
Cheshire Hollow Farm
8.4/10 (15 reviews)
This 94-acre working farm invites visitors to interact with pygmy goats, miniature horses, and other friendly animals. Experience nature hikes, scavenger hunts, and seasonal activities like pumpkin picking and hayrides.
Maplecroft Plaza Shopping Center
8.6/10 (14 reviews)
Maplecroft Plaza serves local Cheshire residents with essential retail shops in a convenient setting. Browse the diverse stores during weekday mornings when the atmosphere is most relaxed and parking is plentiful.
Barker Character, Comic and Cartoon Museum
7.0/10 (12 reviews)
Step back in time at this treasure trove of over 80,000 character toys and memorabilia from 1873 to today. Explore meticulously arranged exhibits that evoke nostalgia across generations of American pop culture.
Bartlem Park
8.6/10 (13 reviews)
This vibrant community hub offers sports fields, a playground, and the Cheshire Community Pool for active pursuits. Enjoy a family picnic in the pavilion area or time your visit for the annual Fall Festival in September.
Drazen Orchards
7.8/10 (10 reviews)
This family-owned orchard invites you to pick seasonal fruits straight from the trees since 1951. Savor the harvest experience with weekend wagon rides and farm-fresh treats at their charming stand.
Lock 12 Historical Park
Discover America's canal history at Lock 12 Historical Park, home to the only intact lock from the 1828 Farmington Canal. Walk the heritage trail after exploring the lock-keeper's house and canal artifacts.
Quinnipiac Recreation Area
8.6/10 (14 reviews)
This 59-acre community park offers well-maintained fields for soccer, lacrosse, and in-line skating. Families can enjoy the pavilion's picnic areas while watching local sports events unfold.
Cheshire Hotel Deals
Cheshire Welcome Inn
1106 S Main St. Cheshire CT
Fully refundableReserve now, pay when you stay
$97 nightly
$111 total
Nov 2 - Nov 3
Total with taxes and fees
8.4/10 Very Good! (891 reviews)
"This is a clean, no frills, and inexpensive motel just outside New Haven. Nothing special, but it has a microwave and a fridge, which is nice."
Reviewed on Oct 13, 2026
The Capitol Hotel
440 Asylum St Hartford CT
Fully refundableReserve now, pay when you stay
$96 nightly
$110 total
Nov 16 - Nov 17
Total with taxes and fees
New Haven Hotel
229 George Street New Haven CT
Fully refundableReserve now, pay when you stay
$138 nightly
$159 total
Oct 26 - Oct 27
Total with taxes and fees
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.
Find the Best Cheshire Vacation Packages
Cheshire Essential Information
Language | English |
|---|---|
Currency | U.S dollars |
Closest Airport | Tweed - New Haven Regional Airport (HVN) |
Population | 29,400 |
Max Temp Winter | 35ºF |
Max Temp Summer | 80ºF |
Top Sights | Lake Compounce, Toyota Presents Oakdale Theatre and Powder Ridge Mountain Park and Resort |
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Frequently asked questions
How much does a Cheshire vacation package cost?
You can pick up a vacation package to this top destination from $475 on Expedia. However, how much your vacation to Cheshire costs will depend on factors like your hotel choice, length of stay and season.
What are the cheapest months to go to Cheshire?
If you're looking to score a cheap Cheshire vacation package, consider traveling in November, December and January. You'll typically find lower rates on flights and accommodations during these quieter months — ideal for a budget-friendly break.
How many days is enough for Cheshire?
With about 2 days, you'll have plenty of time to visit popular neighborhoods such as Milldale and Cheshire Historic District during your Cheshire vacation. Remember to also add Cheshire Hollow Farm and Bartlem Park to your sightseeing itinerary. Searching for more adventures? Consider exploring outside of Cheshire on day trips and tours.
Is it worth booking a vacation package to Cheshire?
From top attractions such as Cheshire Golf Course and Cheshire Hollow Farm to its epic hiking, a Cheshire vacation offers a vibrant mix of experiences. With so much to do and see, 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 cinch with Expedia. After you've entered your preferred dates and destination under our "Packages" tab, set your budget range, apply some filters and browse what's available. You can tailor your search by "Amenities," "Property type," "Traveler experience" and more. Sort the results by "Price: low to high" to discover the most economical Cheshire package deals. Want a simple trick to get even more savings? Have some flexibility with your departure dates and consider traveling on a weekday, when prices are generally lower.
Is it cheaper to book a Cheshire vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your flight, hotel and car rental into one great-value price and you could save hundreds of dollars. You'll typically land a better deal than booking each component individually. And you'll still have the freedom to create a personalized Cheshire vacation by choosing your favorite accommodation type, airline and car class.
When to book a vacation package to Cheshire?
Secure incredible bargains by booking your flights in advance with Expedia. If being spontaneous is more your thing, grab one of our last-minute deals for an impromptu Cheshire adventure.
How to plan a trip to Cheshire?
- Choose when to travel: Check your calendar and get packing. Your preferred time of year and the activities on offer will also help you decide when to escape to Cheshire.
- Plan your budget wisely: In addition to the cost of your accommodations, you'll need to consider other expenses too. These include flights, food and transportation. Also, put aside some extra funds for unexpected costs that could arise during your trip to Cheshire.
- Use our trip planning tool to explore Cheshire: Research every part of your trip to Cheshire with this comprehensive planner. Invite your family and friends to collaborate on a group trip, search for stays or things to do and make bookings.
- Decide how many days away: Start by compiling a list of the sights and activities you'd like to get to in Cheshire. Then, estimate how long you'll need at each, as well as any travel time.
- Combine your hotel and flights: Epic destination, check. Length of stay, check. All that's left is to choose a Cheshire vacation package that brings all your bookings together.
- Add on excursions and experiences: Read our dedicated travel guide to find some awesome things to do in Cheshire. Book tickets or make reservations before you go to save time and skip the hassle of searching for activities once you arrive.
Does Expedia offer Book Now, Pay Later Cheshire vacation packages?
If you're like us, you love discovering new places but don't love the big price tag that can sometimes come with it. That's why we offer Book Now, Pay Later vacations. With help from online lender Affirm, you can spread the total cost of your Cheshire vacation over 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can secure cheap vacation packages with payment plans as soon as you see them.
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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.
