Cheshire Historic District Holidays

Book a Hotel + Flight or Car together to unlock savings

Top hotels in Cheshire Historic District

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
The price is 3.543.768 ₫ per night from 24 Aug to 25 Aug
3.543.768 ₫
4.075.334 ₫ total
24 Aug - 25 Aug
includes taxes & fees
8.6/10 Excellent! (841 reviews)
"It was lovely aside from multiple homeless people walking around the halls of the hotel and lingering. Otherwise had a very nice stay."

Reviewed on 6 Aug 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
The price is 2.745.863 ₫ per night from 13 Aug to 14 Aug
2.745.863 ₫
3.157.743 ₫ total
13 Aug - 14 Aug
includes taxes & fees
7.8/10 Good! (1,262 reviews)
"Breakfast was good. Staff was great."

Reviewed on 7 Aug 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
The price is 4.174.383 ₫ per night from 24 Aug to 25 Aug
4.174.383 ₫
4.800.541 ₫ total
24 Aug - 25 Aug
includes taxes & fees
8.2/10 Very Good! (1,005 reviews)
Best deal for luxurious stay
"The rooms felt luxurious, with full bath towels, comfortable bed, and extremely clean. We had an issue with the wifi since it didn’t recognize that we were checked it."

Reviewed on 8 Aug 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.

Popular places to visit

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 theatre 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 theatre scene in this romantic area.

Cheshire Golf Course

Roaring Brook Park

Explore the great outdoors at Roaring Brook Park, a lovely green space in Cheshire. Experience the area's entertainment venues and theatre scene.

Roaring Brook Park

Frequently asked questions

How much does a Cheshire Historic District holiday package cost?
You can pick up a holiday package to this top destination on Expedia. But how much your holiday 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?
If you'd like to book a cheap Cheshire Historic District holiday package, consider planning a trip in January, February and March. You're likely to find better prices on hotels and flights during these months — perfect for travellers wishing to save money.
How many days is enough for Cheshire Historic District?
With a well-planned schedule, you can easily visit the most popular Cheshire Historic District attractions in a handful of days. But if you'd like to discover hidden gems or go on day trips, think about booking your Cheshire Historic District holiday for longer.
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 holiday package as early as possible.
Is it cheaper to book a Cheshire Historic District holiday as a package?
An Expedia holiday package could save you hundreds of dollars when compared to arranging flights and hotels individually. Better still, you can personalise 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 holiday 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.
How to plan a trip to Cheshire Historic District?

  1. Choose when to travel: Check your calendar and get your bags packed. Your preferred season and the activities on offer will also help you decide when to holiday in Cheshire Historic District.
  2. Set your budget: Consider expenses such as flights, meals and transportation when working out how much to set aside for your trip to Cheshire Historic District. Then, choose a property that matches your budget, whether that's an affordable option or a swankier retreat.
  3. Decide how many days away: Start by making a list of all the activities and attractions you'd like to experience in Cheshire Historic District. Then, estimate how long you'll need at each, along with any travel time.
  4. Combine your flights and hotel: Epic destination, check. Length of stay, check. All that's left now is to find a Cheshire Historic District holiday package that brings all your bookings together.