Cheshire Historic District Vacations from $391

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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.
Cambria Hotel New Haven University Area

Cambria Hotel New Haven University Area

3 out of 5
West River
Save 100% on your flight
per person
Sep 23 - Sep 27
found 1 day ago
Roundtrip flight included
Tampa (TPA) to New Haven (HVN)
8.8/10 Excellent! (838 reviews)
First time staying at this hotel and I am happy to announce.The hotel was phenomenal.Great service very clean outside was bright and clear.Access to the hotel was wonderful. My hotel room was awesome.It was clean.The bathroom was clean.The bed was fresh.The countertops were sparkling and shiny.The towels were very soft and plush, there was. Nothing that I needed.I did not get. It was a pleasure for me to stay at this hotel and giving the opportunity for me to spend time with my family and friends.I will visit this hotel again and again.During my future stays in new haven.

Reviewed on Aug 11, 2025

Graduate by Hilton New Haven

Graduate by Hilton New Haven

4 out of 5
Downtown New Haven
Save 100% on your flight
per person
Sep 23 - Sep 27
found 1 day ago
Roundtrip flight included
Tampa (TPA) to New Haven (HVN)
9.2/10 Wonderful! (851 reviews)
Great hotel in the niddle of town. A block from the Museum of Art. Park around thr corner..no parking on site.

Reviewed on Aug 11, 2025

Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

2.5 out of 5
per person
Sep 19 - Sep 26
found 1 day ago
Roundtrip flight included
San Juan (SJU) to New Haven (HVN)
8.8/10 Excellent! (1,052 reviews)
The convenience of the shopping mall with restaurants. There was plenty of parking without having to walk much to far from the hotel.

Reviewed on Aug 11, 2025

Luxury Apartments by Hyatus at Pierpont

Luxury Apartments by Hyatus at Pierpont

4 out of 5
The Hill
Save 100% on your flight
per person
Sep 23 - Sep 27
found 1 day ago
Roundtrip flight included
Tampa (TPA) to New Haven (HVN)
9.4/10 Exceptional! (19 reviews)
Excellent location downtown and close to yale. A lot of complimentary amenities and activities. Very nice size rooms. A nice residential feel for a weeks stay.

Reviewed on Jun 27, 2025

Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

4 out of 5
Downtown New Haven
Save 100% on your flight
per person
Sep 23 - Sep 27
found 1 day ago
Roundtrip flight included
Tampa (TPA) to New Haven (HVN)
8.4/10 Very Good! (1,011 reviews)
Amazing stay, great view and comfortable accommodations. Only complaint is lower floors are subject to street noise which is out of the hotel’s control. Would 100% stay here again when returning to New Haven

Reviewed on Aug 12, 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

Cambria Hotel New Haven University Area

Cambria Hotel New Haven University Area

3 out of 5
20 Dwight Street, New Haven, CT
Fully refundableReserve now, pay when you stay
$135 nightly
The price is $155 total per night from Aug 26 to Aug 27
$155 total
Aug 26 - Aug 27
Total includes taxes and fees
8.6/10 Excellent! (844 reviews)
"Loved staying here - staff was super nice. My daughter and I had a great time."

Reviewed on Aug 9, 2025

Cambria Hotel New Haven University Area
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
$105 nightly
The price is $120 total per night from Aug 18 to Aug 19
$120 total
Aug 18 - Aug 19
Total includes taxes and fees
7.8/10 Good! (1,266 reviews)
"Check in was slow as the room would not be ready until 2 pm. At least that what i was told Location is good. Easy access to everything"

Reviewed on Aug 12, 2025

Best Western Executive Hotel Of New Haven - West Haven
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
$151 nightly
The price is $174 total per night from Aug 26 to Aug 27
$174 total
Aug 26 - Aug 27
Total includes taxes and fees
8.2/10 Very Good! (1,006 reviews)
"Great hotel near Yale with friendly staff"

Reviewed on Aug 10, 2025

Omni New Haven Hotel at Yale
See all 784 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.

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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 $391 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.