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 $1,349, price is now CA $1,183 per person
CA $1,183
per person
Aug 24 - Aug 28
found 3 hours ago
Roundtrip non-stop flight included
Toronto (YTO) 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 $1,454, price is now CA $1,301 per person
CA $1,301
per person
Aug 24 - Aug 28
found 3 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Rochester (ROC)
7.4/10 Good! (1,000 reviews)
It looks like it hadn’t been cleaned in weeks. The walk from the parking garage to the lobby was sketchy. My wife couldn’t sleep. We left at 5 AM.

Reviewed on Jul 6, 2026

Inn on Broadway

Inn on Broadway

3.5 out of 5
Downtown Rochester
Price was CA $1,628, price is now CA $1,488 per person
CA $1,488
per person
Aug 24 - Aug 28
found 3 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Rochester (ROC)
9/10 Wonderful! (983 reviews)
A/c could have been better but overall a fantastic stay

Reviewed on Jul 2, 2026

Woodcliff Hotel and Spa

Woodcliff Hotel and Spa

4 out of 5
Price was CA $1,444, price is now CA $1,333 per person
CA $1,333
per person
Aug 24 - Aug 28
found 3 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Rochester (ROC)
8.4/10 Very good! (1,008 reviews)
Everything perfect

Reviewed on Jul 7, 2026

Hotel on Monroe, BW Signature Collection

Hotel on Monroe, BW Signature Collection

2.5 out of 5
Brighton
Price was CA $1,443, price is now CA $1,335 per person
CA $1,335
per person
Aug 24 - Aug 28
found 3 hours ago
Roundtrip non-stop flight included
Toronto (YTO) to Rochester (ROC)
8.2/10 Very good! (420 reviews)
To be honest with all of you I don’t know why this area is expensive during the weekend but for over $200 a night with taxes and fees I think this place is expensive. Besides this, the room door never fully locked if you left your room, towels smelled clean but had stains on them and the mini fridge well was too small and did not work. More like a motel than a hotel or inn.

Reviewed on Jun 28, 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 13 to Jul 14
CA $203
CA $230 total
Jul 13 - Jul 14
includes taxes & fees
8.2/10 Very good! (1,137 reviews)
"Good property next to lake. Staff needs to be more accommodating to customers."

Reviewed on Jul 9, 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
Fully refundableReserve now, pay when you stay
The price is CA $536 per night from Jul 26 to Jul 27
CA $536
CA $670 total
Jul 26 - Jul 27
includes taxes & fees
9.4/10 Exceptional! (517 reviews)
"The place was beautiful!!"

Reviewed on Jul 8, 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 $167 per night from Jul 22 to Jul 23
CA $167
CA $192 total
Jul 22 - Jul 23
includes taxes & fees
8.8/10 Excellent! (1,016 reviews)
"Location of the hotel is convenient with lot of eateries at walking distance. Parking is easily available at all times. Staff is supportive. Rooms, including washrooms, are neat & clean. TV should have more channels available. Even the main news channels are missing. Breakfast is just ok, but there ..."

Reviewed on Jul 8, 2026

Microtel by Wyndham Penn Yan Finger Lakes Region
See all 1,492 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
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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 $1,183 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.