Cheshire Vacation Packages

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Your Cheshire Vacation

When an adventure in the city is calling your name, answer it with a Cheshire vacation package. With all your travel needs taken care of before you go, all you have to do here is focus on enjoying yourself. Like to explore your new surroundings? Mount Greylock, Mount Greylock State Reservation and East Hoosac Quaker Meetinghouse are just a few of the best places to visit during a trip to Cheshire. Don't delay visiting this destination any longer. The ultimate Cheshire vacation is a few quick clicks away with Expedia.

Top Cheshire Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Baymont by Wyndham Latham Albany Airport

Baymont by Wyndham Latham Albany Airport

2.5 out of 5
per person
Aug 22 - Aug 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
6.2/10 (1,368 reviews)
Tough start. Read the reviews about moldy rooms. I get it now. Our first room had a bathroom that required complete renovation or condemnation. Mildew across the entire ceiling. We were given a new room, yay! The bathroom was an upgrade, but still had problems namely a toilet that had been sprayed down with blue cleaner but not wiped up. Room itself was great. It was my third stay there. Before it was just a dilapidated hallway. That was ok To deal with. Bathrooms are not. Still a reasonable place, with the right room, for one person who needs to hold over for 12 or less hours. Not recommended for more than a one night stay.

Reviewed on Jul. 13, 2025

Park Manor Hotel

Park Manor Hotel

4 out of 5
per person
Aug 22 - Aug 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
8.2/10 Very Good! (1,113 reviews)
We have a great time

Reviewed on Jul. 19, 2025

Hilton Garden Inn Albany Airport

Hilton Garden Inn Albany Airport

3 out of 5
per person
Aug 22 - Aug 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
7.8/10 Good! (1,174 reviews)
Can’t beat the convenience to the airport. The staff is always pleasant and helpful. Have stayed here the night before an early flight many times.

Reviewed on Jul. 14, 2025

Hyatt Place Albany/Downtown

Hyatt Place Albany/Downtown

3 out of 5
Downtown Albany
per person
Aug 22 - Aug 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
9/10 Wonderful! (1,007 reviews)
It was clean and room was spacious. Only thing missing was a pool.

Reviewed on Jul. 15, 2025

Hampton Inn Albany-Wolf Road (Airport)

Hampton Inn Albany-Wolf Road (Airport)

2.5 out of 5
per person
Aug 22 - Aug 24
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Albany (ALB)
8.6/10 Excellent! (1,001 reviews)
The staff accommodated my needs when I missed my flight. It was safe and clean in the area.

Reviewed on Jul. 18, 2025

Ready to book your vacation to Cheshire?

 

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Cheshire Hotel Deals

Vacation Village in the Berkshires

Vacation Village in the Berkshires

3 out of 5
276 Brodie Mountain Rd, Williamstown, MA
Fully refundableReserve now, pay when you stay
The price is CA $118 per night from Jul 20 to Jul 21
CA $118
CA $147 total
Jul 20 - Jul 21
includes taxes & fees
8.6/10 Excellent! (1,883 reviews)
"This is a great get away! Beautiful atmosphere and lots of variety of activities"

Reviewed on Jul. 17, 2025

Vacation Village in the Berkshires
The Williams Inn

The Williams Inn

4 out of 5
101 Spring Street, Williamstown, MA
Fully refundableReserve now, pay when you stay
The price is CA $325 per night from Aug 18 to Aug 19
CA $325
CA $364 total
Aug 18 - Aug 19
includes taxes & fees
9.6/10 Exceptional! (469 reviews)
"Hrwat"

Reviewed on Jul. 11, 2025

The Williams Inn
Hotel Downstreet, Ascend Hotel Collection

Hotel Downstreet, Ascend Hotel Collection

3 out of 5
40 Main St, North Adams, MA
Fully refundableReserve now, pay when you stay
The price is CA $221 per night from Aug 18 to Aug 19
CA $221
CA $246 total
Aug 18 - Aug 19
includes taxes & fees
8.6/10 Excellent! (1,000 reviews)
"Great place"

Reviewed on Jul. 16, 2025

Hotel Downstreet, Ascend Hotel Collection
See all 1,009 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.

All Inclusive Vacations

All Inclusive Vacations

Beach Vacations

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Cheshire vacation package cost?
You can grab a vacation package to this popular destination from CA $891 on Expedia. However, how much your vacation to Cheshire costs will depend on the season, hotel choice and length of stay.
What are the cheapest months to go to Cheshire?
The off-season is the best time to head to Cheshire if you're trying to save. Another tip for scoring cheap Cheshire vacation packages? Try to avoid public holidays and any major events or festivals.
How many days is enough for Cheshire?
Generally, a handful of days is enough to go to the main attractions during your Cheshire vacation. But if you want to have more time to rest or go on day trips, think about extending your trip.
How to find the best Cheshire package deals?
Begin your search for a Cheshire package deal by entering your destination and preferred trip dates under our "Packages" tab. Then add a few filters, like "Property type" and "Amenities," to fine-tune the results to your exact style. You can also sort by "Package discount" and browse offers that come with huge savings. If you don't find the ideal Cheshire package deal straight away, just switch up your dates and search again. Remember that deals are only available for a limited time, so book early and get your Cheshire adventure off to a flying start.
Is it cheaper to book a Cheshire vacation as a package?
Expedia vacation packages are designed to help you keep more cash in your pocket. Bundle your flight, car rental and hotel into one great-value price and you could save hundreds of dollars. You'll generally get a better deal than booking each component separately. And you'll still enjoy the freedom to create a personalized Cheshire vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation package to Cheshire?
If you're considering a spur-of-the-moment Cheshire vacation, check out our last-minute deals that can be booked up to one week before you take off. Don't want to leave things to the last minute? You can land sensational deals on your flights and hotels by booking ahead.
How to plan a trip to Cheshire?

  1. Choose your dates: The things you'd like to do in Cheshire and your favourite season can help you decide when to get away.
  2. Figure out your budget: Ensure you have enough money to pay for everything from transportation and dining out to flights and experiences. Your accommodations will probably be the largest expense during your trip to Cheshire.
  3. Work out your trip length: Consider how much time you want to spend exploring Cheshire. Plan your itinerary so you can get to all the attractions and experiences you're interested in without rushing.
  4. Combine your hotel and flights: Awesome destination, check. Length of stay, check. All that's left now is to find a Cheshire vacation package that brings all your bookings together.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.