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.
Woodcliff Hotel and Spa

Woodcliff Hotel and Spa

4 out of 5
per person
Sep 11 - Sep 18
found 21 hours ago
Roundtrip flight included
Toronto (YYZ) to Rochester (ROC)
8.4/10 Very Good! (1,001 reviews)
Nice and quiet. Liked their breakfast a lot

Reviewed on Jun. 30, 2025

The Strathallan Rochester Hotel & Spa - DoubleTree by Hilton

The Strathallan Rochester Hotel & Spa - DoubleTree by Hilton

4 out of 5
Downtown Rochester
per person
Aug 19 - Aug 26
found 4 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to Rochester (ROC)
8.8/10 Excellent! (815 reviews)
The property was covenient to the downtown. The renovated gym was excellent. The staff were friendly.

Reviewed on Jul. 2, 2025

DoubleTree by Hilton Rochester

DoubleTree by Hilton Rochester

4 out of 5
per person
Aug 19 - Aug 26
found 4 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to Rochester (ROC)
8/10 Very Good! (1,002 reviews)
In addition to no AC in lobby, elevators didn’t work

Reviewed on Jun. 24, 2025

Hilton Garden Inn Rochester Downtown, NY

Hilton Garden Inn Rochester Downtown, NY

3 out of 5
Downtown Rochester
per person
Sep 11 - Sep 18
found 21 hours ago
Roundtrip flight included
Toronto (YYZ) to Rochester (ROC)
8.4/10 Very Good! (786 reviews)
I was first one on the line . But last one check it. They say offer my free breakfast but they never did . I don’t care about breakfast anyway ，just Since you said it and didn't do it, just did it perfunctorily.

Reviewed on Jun. 1, 2025

Inn on Broadway

Inn on Broadway

3.5 out of 5
Downtown Rochester
per person
Aug 19 - Aug 26
found 4 hours ago
Roundtrip non-stop flight included
Ottawa (YOW) to Rochester (ROC)
9/10 Wonderful! (682 reviews)
Was there for a friend’s wedding (best man). When a last minute transportation problem developed, the desk clerk (Liz) drove me to the wedding. All the staff were personable and professional. The room was immaculate and comfortable.

Reviewed on Jul. 3, 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 $191 per night from Aug 3 to Aug 4
CA $191
CA $217 total
Aug 3 - Aug 4
includes taxes & fees
8.2/10 Very Good! (1,004 reviews)
"Room was great. Pool is green. Elevator still doesn’t work."

Reviewed on Jun. 30, 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
Fully refundableReserve now, pay when you stay
The price is CA $466 per night from Jul 14 to Jul 15
CA $466
CA $587 total
Jul 14 - Jul 15
includes taxes & fees
9.2/10 Wonderful! (333 reviews)
"Absolutely beautiful property!"

Reviewed on Jul. 1, 2025

The Lake House on Canandaigua
Days Inn by Wyndham Geneva/Finger Lakes
Days Inn by Wyndham Geneva/Finger Lakes
2 out of 5
485 Hamilton St, Geneva, NY
Fully refundableReserve now, pay when you stay
The price is CA $104 per night from Aug 4 to Aug 5
CA $104
CA $115 total
Aug 4 - Aug 5
includes taxes & fees
7.2/10 Good! (1,016 reviews)
Needs to Upgrade Linen and Towels
"The room and hotel seemed to be clean enough overall. Continental breakfast was all right, but a little skimpy on choices. The only problem we could see was the sheets, bedspread and towels need to be replaced. The sheets on our bed were paper thin with weird stains dried into them. We left the sheet ..."

Reviewed on Jun. 30, 2025

Days Inn by Wyndham Geneva/Finger Lakes
See all 1,423 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

Beach Vacations

Family Vacations

Family Vacations

Frequently asked questions

How much does a Middlesex vacation package cost?
Offering excellent value package deals from CA $1,401 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.