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.
Hyatt Regency Rochester

Hyatt Regency Rochester

3.5 out of 5
Downtown Rochester
Price was CA $1,438, price is now CA $1,247 per person
CA $1,247
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Rochester (ROC)
7.6/10 Good! (1,000 reviews)
As a loyal Hyatt member for over three years, I was extremely disappointed to learn that the shuttle service prioritizes flight crew over paying guests. This experience left me feeling undervalued and frustrated. I hope Hyatt reconsiders this policy to ensure all guests receive equal and fair treatment.

Reviewed on Aug. 18, 2025

Hotel Canandaigua, Tapestry Collection by Hilton

Hotel Canandaigua, Tapestry Collection by Hilton

3.5 out of 5
Price was CA $1,819, price is now CA $1,520 per person
CA $1,520
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Rochester (ROC)
9/10 Wonderful! (227 reviews)
Beautiful setting overlooking the Lake. Staff was courteous and helpful. Indoor & outdoor seating, good food.

Reviewed on Aug. 19, 2025

The Strathallan Rochester Hotel & Spa - DoubleTree by Hilton

The Strathallan Rochester Hotel & Spa - DoubleTree by Hilton

4 out of 5
Downtown Rochester
Price was CA $1,497, price is now CA $1,340 per person
CA $1,340
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Rochester (ROC)
8.8/10 Excellent! (844 reviews)
Nice property in a great area.

Reviewed on Aug. 17, 2025

School 31 Lofts at Colors Studios

School 31 Lofts at Colors Studios

2.5 out of 5
Downtown Rochester
Price was CA $1,393, price is now CA $1,270 per person
CA $1,270
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Rochester (ROC)
8.8/10 Excellent! (492 reviews)
Lovely place to gwt ready for my wedding Walking distance from the venue and great restaurants near by

Reviewed on Aug. 9, 2025

Hilton Garden Inn Rochester Downtown, NY

Hilton Garden Inn Rochester Downtown, NY

3 out of 5
Downtown Rochester
Price was CA $1,543, price is now CA $1,420 per person
CA $1,420
per person
Oct 9 - Oct 13
found 1 day ago
Roundtrip non-stop flight included
Montreal (YUL) to Rochester (ROC)
8.2/10 Very Good! (807 reviews)
It was not the most terrible stay but it wasn’t the most comfortable either. The hotel was understaffed so no room service, dining options are limited if you arrive late.

Reviewed on Aug. 18, 2025

Ready to book your vacation to Middlesex?

 

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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 $161 per night from Sep 1 to Sep 2
CA $161
CA $183 total
Sep 1 - Sep 2
includes taxes & fees
8.2/10 Very Good! (1,010 reviews)
"Wonderful place highly recommend"

Reviewed on Aug. 16, 2025

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 $431 per night from Sep 4 to Sep 5
CA $431
CA $549 total
Sep 4 - Sep 5
includes taxes & fees
9.2/10 Wonderful! (369 reviews)
The old hotel. The facility needs some updating.
"The facility needs to be updated to be a modern first class destination. The rooms are missing some of the basic that are found in most every decent hotel. The shower didn't work properly, no trash can, no hair dryer, only 2 hangers in the closet etc. For the price we will find another first class ..."

Reviewed on Aug. 15, 2025

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 $164 per night from Aug 25 to Aug 26
CA $164
CA $183 total
Aug 25 - Aug 26
includes taxes & fees
8.6/10 Excellent! (1,012 reviews)
"The hotel was conveniently located. Everything was within walking distance. However breakfast wasn’t great; only a few options. When we checked in the room did not have toilet paper which was disappointing however the hotel staff stepped right in to bring some to our room. The bathroom was tiny and ..."

Reviewed on Aug. 16, 2025

Microtel by Wyndham Penn Yan Finger Lakes Region
See all 1,428 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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
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Family Vacations
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Frequently asked questions

How much does a Middlesex vacation package cost?
Offering excellent value package deals from CA $1,247 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.

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