Cheshire Historic District Vacations from $220

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Your Cheshire Historic District Vacation

When you organize a vacation package to Cheshire Historic District, you can relax and enjoy your escape knowing that all your travel plans are under control. Uncover the wonders of this amazing city while based in a neighborhood like Prospect Hill, which is good for history. If a sightseeing tour is on the to-do list during your trip to Cheshire Historic District, look around leading attractions like Cheshire Golf Course, Cheshire Hollow Farm and Barker Character, Comic and Cartoon Museum. Don't delay your visit to this city any longer. Your dream Cheshire Historic District vacation is a couple of clicks away with Expedia.

The Latest Cheshire Historic District vacation packages

Price found within the past 48 hours. Click for updated prices.
Motel 6 Niantic, CT - New London

Motel 6 Niantic, CT - New London

2 out of 5
Price was $264, price is now $220 per person
$220
per person
Nov 21 - Nov 24
found 4 hours ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
7/10 Good! (1,002 reviews)
Ample parking, easily accessible off the highway, friendly staff

Reviewed on Sep 27, 2025

Madison Beach Hotel

Madison Beach Hotel

4 out of 5
Madison Center
Save 100% on your flight
Price was $1,869, price is now $1,349 per person
$1,349
per person
Dec 22 - Dec 28
found 4 hours ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
9.4/10 Exceptional! (316 reviews)
the staff was exceptional and our dinner was very good

Reviewed on Sep 17, 2025

Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

2.5 out of 5
Price was $556, price is now $446 per person
$446
per person
Nov 19 - Nov 23
found 20 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to New Haven (HVN)
8.8/10 Excellent! (1,092 reviews)
This hotel was convenient for us because it is located close to family. The room was clean, and the front desk staff were very helpful. During our stay, on a Friday night, tnere was a lot of loud noise from a nearby room. We called the front desk, and they handled the matter. The free breakfast was good.

Reviewed on Oct 2, 2025

Hilton Garden Inn Hartford North/Bradley Int'l Airport

Hilton Garden Inn Hartford North/Bradley Int'l Airport

3 out of 5
Price was $611, price is now $494 per person
$494
per person
Nov 19 - Nov 23
found 20 hours ago
Roundtrip non-stop flight included
Atlanta (ATL) to New Haven (HVN)
8.8/10 Excellent! (1,005 reviews)
Yes it was very nice

Reviewed on Oct 3, 2025

Hampton Inn Milford

Hampton Inn Milford

2.5 out of 5
Price was $383, price is now $314 per person
$314
per person
Nov 21 - Nov 24
found 4 hours ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
8/10 Very Good! (1,006 reviews)
Room is clean and everything ran smoothly

Reviewed on Oct 4, 2025

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Discover the most popular places to visit in Cheshire Historic District

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 Historic District Hotel Deals

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 19 to Oct 20
$192 total
Oct 19 - Oct 20
Total with taxes and fees
8.4/10 Very Good! (1,016 reviews)
"Charged for WiFi. Hotel crowded with uncourteous group members in packs - made elevators slow."

Reviewed on Sep 29, 2025

Omni New Haven Hotel at Yale
New Haven Hotel

New Haven Hotel

3.5 out of 5
229 George Street, New Haven, CT
Fully refundableReserve now, pay when you stay
$119 nightly
The price is $137 total per night from Oct 26 to Oct 27
$137 total
Oct 26 - Oct 27
Total with taxes and fees
9/10 Wonderful! (1,804 reviews)
"Let me start off by saying that I first came during Christmas and New Years of 2024 and it was solely because of my experience with interacting with Diahema or Dlahema. The lady at the front desk was super sweet, friendly and very inviting. Being introduced to the hotel from her made me want to come ..."

Reviewed on Oct 1, 2025

New Haven Hotel
Red Roof Inn Meriden

Red Roof Inn Meriden

2 out of 5
10 Bee St, Meriden, CT
Fully refundableReserve now, pay when you stay
$99 nightly
The price is $114 total per night from Oct 5 to Oct 6
$114 total
Oct 5 - Oct 6
Total with taxes and fees
7.4/10 Good! (1,000 reviews)
"Clean rooms"

Reviewed on Sep 28, 2025

Red Roof Inn Meriden
See all 798 properties in Cheshire Historic District
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 Historic District Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Tweed - New Haven Regional Airport (HVN)
Max Temp Winter
35ºF
Max Temp Summer
80ºF
Top Sights
Barker Museum, Cheshire Golf Course and Cheshire Hollow Farm

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Frequently asked questions

How much does a Cheshire Historic District vacation package cost?
You can pick up a vacation package to this top destination from $220 on Expedia. But how much your vacation to Cheshire Historic District costs will depend on factors like the season, length of stay and hotel choice.
What are the cheapest months to go to Cheshire Historic District?
You can usually find lower rates and greater availability in December, January and February. Take a look at our cheap Cheshire Historic District vacation packages and you could get some excellent off-season deals.
How many days is enough for Cheshire Historic District?
Usually, a handful of days is enough to tick off the major attractions during your Cheshire Historic District vacation. However, if you prefer to have more time to relax or take day trips, think about extending your itinerary.
How to find the best Cheshire Historic District package deals?
Use Expedia's handy filters to find some of the best Cheshire Historic District package deals. When you begin your search, just set your maximum budget and then order the results by "Price: low to high." If you want to save, plan your break for midweek, or search for Cheshire Historic District package deals in the off-peak season. Play around with your travel dates and you may score even better discounts. As a rule of thumb, it's typically best to book your vacation package as early as possible.
Is it cheaper to book a Cheshire Historic District vacation as a package?
An Expedia vacation package could save you hundreds of dollars when compared to arranging flights and hotels individually. Better still, you can personalize your Cheshire Historic District escape to match your exact style. Choose your preferred flight time, select the hotel type and add a car rental. Browse our bundle deals and find out how much you can save.
When to book a vacation package to Cheshire Historic District?
Enjoy fantastic discounts by reserving your flights ahead of time with Expedia. If being spontaneous is more your style, snap up one of our last-minute deals for a spur-of-the-moment Cheshire Historic District trip.
Does Expedia offer Book Now, Pay Later Cheshire Historic District vacation packages?
If you're anything like us, you love exploring new places but don't love the big price tag that can come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can spread the overall cost of your Cheshire Historic District vacation over 3, 6 or 12 months. There are also no late payment fees or hidden costs, so you can snap up great vacation packages with payment plans as soon as you spot them.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.