Middlesex Vacation Packages

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Your Middlesex Vacation

With everything organized before you set off, our Middlesex vacation packages mean you can simply focus on vacationing! One neighborhood to base yourself in this fascinating city is Bristol Hills, which is great for camping and hiking. Eager to see the sights? Spend your days enjoying top attractions like Clarks Gully during your trip to Middlesex. Browse Expedia's extensive range of travel options and book your ultimate vacation to Middlesex today.

Top Middlesex Vacation Deals

Price found within the past 48 hours. Click for updated prices.
RIT Inn & Conference Center

RIT Inn & Conference Center

3.5 out of 5
Price was CA $942, price is now CA $822 per person
CA $822
per person
Oct 2 - Oct 4
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Rochester (ROC)
8.4/10 Very good! (1,003 reviews)
Beds were comfy, pool area was lovely, was very quiet and relaxing

Reviewed on Jul 7, 2026

Hyatt Regency Rochester

Hyatt Regency Rochester

3.5 out of 5
Downtown Rochester
Price was CA $1,083, price is now CA $883 per person
CA $883
per person
Oct 2 - Oct 4
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Rochester (ROC)
7.4/10 Good! (1,000 reviews)
👍

Reviewed on Jul 12, 2026

Woodcliff Hotel and Spa

Woodcliff Hotel and Spa

4 out of 5
Price was CA $1,022, price is now CA $927 per person
CA $927
per person
Oct 2 - Oct 4
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Rochester (ROC)
8.4/10 Very good! (1,008 reviews)
Swimming pool was closed while we were there but everything else is great.

Reviewed on Jul 12, 2026

Hampton Inn Rochester Penfield

Hampton Inn Rochester Penfield

2.5 out of 5
Price was CA $1,243, price is now CA $1,131 per person
CA $1,131
per person
Oct 2 - Oct 4
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Rochester (ROC)
9/10 Wonderful! (1,006 reviews)
Great location to stay super clean rooms, friendly staff and everything is nearby within walking distance super quiet couldn’t ask for a better place to stay

Reviewed on Jul 13, 2026

School 31 Lofts at Colors Studios

School 31 Lofts at Colors Studios

2.5 out of 5
Downtown Rochester
Price was CA $1,138, price is now CA $1,041 per person
CA $1,041
per person
Oct 2 - Oct 4
found 1 day ago
Roundtrip non-stop flight included
Vancouver (YVR) to Rochester (ROC)
8.8/10 Excellent! (570 reviews)
We were very dissatisfied with our room. It would have been fine for one person, but even after 55 years of marriage, we like to have some privacy while using the toilet and shower. I would suggest that you remove the huge bathtub in Loft 215 and enclose the area where the toilet and shower are. Also, the shower had no shelf for shampoo, conditioner and bath gel. There was also no coffee pot in our room. I could understand this if the hotel provided coffee elsewhere in the hotel. A very helpful real person named David provided us with coffee supplies and even a little table to put it on. Again, if the bathtub was removed there would be room for a coffee station. Finally, the doorknob was falling off the door to the balcony, which was really dirty.

Reviewed on Jul 12, 2026

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Middlesex Hotel Deals

41 Lakefront Hotel, Trademark Collection By Wyndham

41 Lakefront Hotel, Trademark Collection By Wyndham

3 out of 5
41 Lake Front Blvd Geneva NY
Fully refundableReserve now, pay when you stay
The price is CA $203 per night from Jul 15 to Jul 16
CA $203
CA $230 total
Jul 15 - Jul 16
includes taxes & fees
8.2/10 Very good! (1,148 reviews)
"Great location. Convenient to downtown Geneva. Pool was out of order which would have been nice to know before booking. No a/c in many of the hallways."

Reviewed on Jul 14, 2026

41 Lakefront Hotel, Trademark Collection By Wyndham
The Lake House on Canandaigua

The Lake House on Canandaigua

4.5 out of 5
770 South Main Street Canandaigua NY
The price is CA $566 per night from Jul 22 to Jul 23
CA $566
CA $703 total
Jul 22 - Jul 23
includes taxes & fees
9.4/10 Exceptional! (525 reviews)
"The staff was top notch. Everyone was super accommodating."

Reviewed on Jul 13, 2026

The Lake House on Canandaigua
Microtel by Wyndham Penn Yan Finger Lakes Region

Microtel by Wyndham Penn Yan Finger Lakes Region

3 out of 5
124 Elm St Penn Yan NY
Fully refundableReserve now, pay when you stay
The price is CA $158 per night from Jul 15 to Jul 16
CA $158
CA $182 total
Jul 15 - Jul 16
includes taxes & fees
8.8/10 Excellent! (1,000 reviews)
"The rooms were clean. Staff was good but a smile on the face would make the customer feel welcome. Same breakfast was served everyday. they can do a variety. Ample parking."

Reviewed on Jul 13, 2026

Microtel by Wyndham Penn Yan Finger Lakes Region
See all 1,487 properties in Middlesex
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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Stay near popular Middlesex attractions

Clarks Gully

Commune with nature and explore the great outdoors at Clarks Gully during your travels in Middlesex. Stroll along this relaxing area's lakeside, or simply enjoy its wineries.
See properties

Frequently asked questions

How much does a Middlesex vacation package cost?
Offering excellent value package deals from CA $822 on Expedia, you'll be thrilled with how little a vacation to Middlesex costs! Expedia's packages make travel planning easier and your savings go further.
What are the cheapest months to go to Middlesex?
January, February and March are great times to look for cheap Middlesex vacation packages. Choosing to travel in quieter months means you can typically find reduced prices on flights and accommodations.
How many days is enough for Middlesex?
With a well-planned itinerary, you can easily tick off the most popular Middlesex attractions in a few days. But if you want to explore off the beaten track or go on day tours, consider booking your Middlesex vacation for longer.
How to find the best Middlesex package deals?
Use Expedia's filters to help you find some terrific Middlesex package deals. When you begin your search, simply set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your trip for midweek, or browse for Middlesex package deals in the low season. Switch up your travel dates and you may land even better discounts. As a rule of thumb, it's usually best to book your vacation package as soon as possible.
Is it cheaper to book a Middlesex vacation as a package?
You can enjoy significant savings on your Middlesex escape by booking a tailored vacation package. Click on the "Package" heading, then select your destination and travel dates to see some great flight and hotel prices. Bundle everything into a great-value package and you can save hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a vacation package to Middlesex?
If you're planning a spur-of-the-moment Middlesex vacation, browse our last-minute deals that can be booked up to a week before you go. Don't want to leave things to the last minute? You can find amazing deals on your flights and hotels by booking ahead.
How to plan a trip to Middlesex?

  1. Pick your travel dates: The things you plan to do in Middlesex and your favourite season can help you decide when to go.
  2. Budget wisely: In addition to the price of your accommodations, you'll need to factor in other expenses too. These include transportation, food and flights. Also, put aside some extra funds for unexpected costs that could crop up during your trip to Middlesex.
  3. Set the duration of your trip: Start by making a list of all the sights and activities you want to get to in Middlesex. Then, estimate how long you'll need at each, as well as any travel time.
  4. Combine your flights and hotel: Awesome destination, check. Length of stay, check. All that's left is to pick a Middlesex vacation package that brings all your bookings together.

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