Cheshire Vacations from $570

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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.
Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

4 out of 5
Downtown New Haven
Price was $712, price is now $570 per person
$570
per person
Jan 5 - Jan 9
found 1 day ago
Roundtrip flight included
Tampa (TPA) to New Haven (HVN)
8.6/10 Excellent! (1,105 reviews)

Graduate by Hilton New Haven

Graduate by Hilton New Haven

4 out of 5
Downtown New Haven
Price was $720, price is now $601 per person
$601
per person
Jan 5 - Jan 9
found 1 day ago
Roundtrip flight included
Tampa (TPA) to New Haven (HVN)
9.2/10 Wonderful! (1,002 reviews)

Landing Apartments New Haven Near Dixwell

Landing Apartments New Haven Near Dixwell

3 out of 5
Newhallville
Price was $939, price is now $786 per person
$786
per person
Dec 22 - Dec 26
found 21 hours 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

Landing Furnished Apartment Near Yale University

Landing Furnished Apartment Near Yale University

3 out of 5
Downtown New Haven
Price was $777, price is now $672 per person
$672
per person
Dec 22 - Dec 26
found 21 hours ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
2/10 (2 reviews)

Hyatus Luxury Residences City Crossing

Hyatus Luxury Residences City Crossing

4 out of 5
The Hill
Price was $1,095, price is now $950 per person
$950
per person
Dec 22 - Dec 26
found 21 hours ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
9.2/10 Wonderful! (35 reviews)
Bed had no mattress cover but was very comfortable. Only one working lamp. Vents could use a good cleaning. I would recommend it and would stay again.

Reviewed on Oct 25, 2026

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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.
See properties

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
$97 nightly
The price is $111 total per night from Nov 2 to Nov 3
$111 total
Nov 2 - Nov 3
Total with taxes and fees
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
$109 nightly
The price is $125 total per night from Nov 2 to Nov 3
$125 total
Nov 2 - Nov 3
Total with taxes and fees
The Capitol Hotel
New Haven Hotel

New Haven Hotel

3.5 out of 5
229 George Street New Haven CT
$132 nightly
The price is $152 total per night from Nov 27 to Nov 28
$152 total
Nov 27 - Nov 28
Total with taxes and fees
New Haven Hotel
See all 1,329 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.

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 $570 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.

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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.