Cheshire Vacations

Book a Hotel + Flight together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to SARĀ 5,400 when you book a flight and hotel together*

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    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Find the Best Cheshire Vacation Packages

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
The price is SARĀ 335 per night from Jul 30 to Jul 31
SARĀ 335
SARĀ 385 total
30 Jul - 31 Jul
includes taxes & fees
8.4/10 Very Good! (846 reviews)
"Just stayed the night passing through on a roadtrip, property was dated, front desk was rude on checkin when I arrived late. Room was clean enough."

Reviewed on 17 July 2026

Cheshire Welcome Inn
New Haven Hotel

New Haven Hotel

3.5 out of 5
229 George Street New Haven CT
Fully refundableReserve now, pay when you stay
The price is SARĀ 486 per night from Aug 9 to Aug 10
SARĀ 486
SARĀ 558 total
9 Aug - 10 Aug
includes taxes & fees
9.2/10 Wonderful! (2,211 reviews)
"Hotel was a pleasure to stay at. Staff particularly helpful and friendly."

Reviewed on 16 July 2026

New Haven Hotel
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 SARĀ 484 per night from Jul 19 to Jul 20
SARĀ 484
SARĀ 557 total
19 Jul - 20 Jul
includes taxes & fees
Best Western Executive Hotel Of New Haven - West Haven
See all 1,282 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.

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

Frequently asked questions

How much does a Cheshire vacation package cost?
You'll find cheap prices on Expedia for your Cheshire break. However, a range of factors like your choice of hotel, the season and length of stay will determine how much your vacation to Cheshire costs.
What are the cheapest months to go to Cheshire?
If you're looking to book a cheap Cheshire vacation package, consider visiting in December, January and February. You'll typically find lower rates on airfares and hotels during these quieter months ā€” ideal for budget-conscious travelers.
How to find the best Cheshire package deals?
Landing a cheap Cheshire package deal is a breeze with Expedia. After you've entered your preferred dates and destination under our "Packages" tab, set your maximum budget, apply a couple of filters and browse what's available. You can personalize your search by "Property class," "Number of bedrooms," "Traveler experience" and more. Sort the results by "Price: low to high" to view the most wallet-friendly Cheshire package deals. Want a simple trick to get the biggest savings? Be flexible with your departure dates and consider going away on a weekday, when prices are typically lower.
Is it cheaper to book a Cheshire vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your hotel, flight and car rental into one great-value price and enjoy significant savings. You'll usually get a better deal than booking each component separately. And you'll still get the flexibility to create a customized Cheshire vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Cheshire?
Land amazing discounts by booking your flights in advance with Expedia. If spontaneity is more your thing, take advantage of our last-minute deals for an impromptu Cheshire getaway.
How to plan a trip to Cheshire?

  1. Pick your dates: The things you plan to do in Cheshire and your preferred season will help you decide when to travel.
  2. Set a budget: Factor in expenses such as flights, transportation and food when calculating how much to save for your trip to Cheshire. Then, pick a hotel that works with your budget, whether that's an economical option or a more luxurious getaway.
  3. Set the duration of your trip: Start by compiling a list of the attractions you'd like to experience in Cheshire. Then, estimate how long you'll need for each, including any travel time.
  4. Combine your flights and hotel: Awesome destination, check. Length of stay, check. All that's left now is to pick a Cheshire vacation package that brings all your bookings together.