Cheshire Vacations from $293

Book a Hotel + Flight or Car together to unlock savings

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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.
Graduate by Hilton New Haven

Graduate by Hilton New Haven

4 out of 5
Downtown New Haven
Price was $373, price is now $293 per person
$293
per person
Nov 16 - Nov 18
found 23 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to New Haven (HVN)
9.2/10 Wonderful! (877 reviews)
Really creative and thoughtful design with themed tiles, artwork, etc. makes this hotel a lot of fun as well as convenient and comfortable. The high ceilings, large bathroom for a old (remodeled) buildings, and other nice touches were pleasant surprises. It's very close to Yale and plenty of restaurants.

Reviewed on Oct 9, 2025

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
Save 100% on your flight
Price was $1,503, price is now $862 per person
$862
per person
Dec 10 - Dec 13
found 17 hours ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
No reviews
Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

2.5 out of 5
Price was $673, price is now $486 per person
$486
per person
Dec 23 - Dec 30
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
8.8/10 Excellent! (1,092 reviews)
Nice but aged. Back parking lot always seemed to have people hanging out in/around their vehicles and back door stated it was secure 24 hrs but was always propped open or unlocked when we entered over span of 4 days, even at night

Reviewed on Oct 9, 2025

Residence Inn by Marriott Southington

Residence Inn by Marriott Southington

3 out of 5
Price was $712, price is now $527 per person
$527
per person
Dec 23 - Dec 30
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
8.6/10 Excellent! (570 reviews)
It was a perfect place to stay for a wedding weekend. Great family and dog friendly accommodations.

Reviewed on Sep 30, 2025

Days Inn by Wyndham Ridgefield

Days Inn by Wyndham Ridgefield

2 out of 5
Price was $691, price is now $545 per person
$545
per person
Nov 24 - Dec 1
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
5.8/10 (875 reviews)
The room was pretty shabby- with wood peeking through the carpet. No shampoos or other standard conveniences.

Reviewed on Sep 22, 2025

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Discover the most popular places to visit in Cheshire

Cheshire Hollow Farm

Enjoy a stop at Cheshire Hollow Farm, an entertaining place to visit in Cheshire. Take in the theater scene in this romantic area.

Cheshire Hollow Farm

Barker Character, Comic and Cartoon Museum

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.

Barker Character, Comic and Cartoon Museum

Cheshire Golf Course

Enjoy a round of golf in Cheshire at Cheshire Golf Course. Experience the entertainment venues and theater scene in this romantic area.

Cheshire Golf Course

Cheshire Hotel Deals

Cheshire Welcome Inn

Cheshire Welcome Inn

2.5 out of 5
1106 S Main St., Cheshire, CT
$89 nightly
The price is $102 total per night from Oct 13 to Oct 14
$102 total
Oct 13 - Oct 14
Total with taxes and fees
8.4/10 Very Good! (739 reviews)
"We paid $124 for the night for a small, somewhat shabby, basement (downstairs) room with a king sized bed. When we stepped inside the room, there was a concrete step in the doorway which my wife tripped on. Normally, I would expect a room of this quality to cost $75-80. The bed was comfortable enough. ..."

Reviewed on Oct 4, 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
$103 nightly
The price is $118 total per night from Oct 12 to Oct 13
$118 total
Oct 12 - Oct 13
Total with taxes and fees
7.4/10 Good! (1,011 reviews)
"Friendly staff!"

Reviewed on Oct 7, 2025

The Capitol Hotel
Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

4 out of 5
155 Temple St, New Haven, CT
Fully refundableReserve now, pay when you stay
$167 nightly
The price is $192 total per night from Oct 26 to Oct 27
$192 total
Oct 26 - Oct 27
Total with taxes and fees
8.4/10 Very Good! (1,005 reviews)
"We have a lovely stay at the Omni New Haven. The room was clean and quiet with a super comfy bed and pillows. The staff were friendly and helpful. If you are visiting Yale, it's right on the campus. Very walkable!"

Reviewed on Oct 6, 2025

Omni New Haven Hotel at Yale
See all 1,129 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.

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 $293 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?

  1. 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.
  2. 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.
  3. 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.
  4. 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.
  5. 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.
  6. 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.

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.