Middlesex Vacations from $538

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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.

The Latest Middlesex vacation packages

Price found within the past 48 hours. Click for updated prices.
Hotel Canandaigua, Tapestry Collection by Hilton

Hotel Canandaigua, Tapestry Collection by Hilton

3.5 out of 5
Price was $765, price is now $538 per person
$538
per person
Nov 6 - Nov 9
found 15 hours ago
Roundtrip non-stop flight included
San Antonio (SAT) to Rochester (ROC)
9/10 Wonderful! (250 reviews)
This property was gorgeous, overlooking the lake. Loved waking up to that view! Great walking trail along water and park next to property.

Reviewed on Sep 24, 2025

The Lake House on Canandaigua

The Lake House on Canandaigua

4.5 out of 5
Price was $856, price is now $677 per person
$677
per person
Nov 6 - Nov 9
found 15 hours ago
Roundtrip non-stop flight included
San Antonio (SAT) to Rochester (ROC)
9.4/10 Exceptional! (388 reviews)
Property and staff were amazing. The place has a lot to offer. Unfortunately the rooms are not sound proof at all. Maybe because there are no carpets, but we could hear our neighbors from next door and above us. Chairs being slid on floors, dogs barking, people talking loud and walking with hard steps above us. Not a good sleeping experience at all. I mentioned this in a survey by the resort and they didn’t even respond. Go there for the day but don’t stay the night.

Reviewed on Sep 16, 2025

Hilton Garden Inn Rochester/Pittsford

Hilton Garden Inn Rochester/Pittsford

3 out of 5
Price was $775, price is now $621 per person
$621
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
San Antonio (SAT) to Rochester (ROC)
8.6/10 Excellent! (1,001 reviews)
Quiet property. Nice areas for our Dog

Reviewed on Sep 9, 2025

Hampton Inn & Suites Rochester Downtown

Hampton Inn & Suites Rochester Downtown

2.5 out of 5
Downtown Rochester
Price was $755, price is now $606 per person
$606
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
San Antonio (SAT) to Rochester (ROC)
9.6/10 Exceptional! (493 reviews)
Very convenient to the Strong Musem of Play

Reviewed on Sep 28, 2025

Hilton Garden Inn Rochester/University & Medical Center

Hilton Garden Inn Rochester/University & Medical Center

3 out of 5
Price was $733, price is now $590 per person
$590
per person
Nov 6 - Nov 9
found 1 day ago
Roundtrip non-stop flight included
San Antonio (SAT) to Rochester (ROC)
9.2/10 Wonderful! (957 reviews)
Great location in Rochester! Rooms were clean and spacious

Reviewed on Sep 29, 2025

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Discover the most popular places to visit in Middlesex

Cascade at Clark's Gully #Localsecrets #Mybackyard

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.

Clarks Gully

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
$123 nightly
The price is $139 total per night from Oct 19 to Oct 20
$139 total
Oct 19 - Oct 20
Total with taxes and fees
8.2/10 Very Good! (1,045 reviews)
"Great location and staff"

Reviewed on Sep 22, 2025

41 Lakefront Hotel, Trademark Collection By Wyndham
Hotel Canandaigua, Tapestry Collection by Hilton

Hotel Canandaigua, Tapestry Collection by Hilton

3.5 out of 5
205 Lakeshore Drive, Canandaigua, NY
Fully refundableReserve now, pay when you stay
$179 nightly
The price is $203 total per night from Oct 19 to Oct 20
$203 total
Oct 19 - Oct 20
Total with taxes and fees
8.8/10 Excellent! (255 reviews)
"This property was gorgeous, overlooking the lake. Loved waking up to that view! Great walking trail along water and park next to property."

Reviewed on Sep 24, 2025

Hotel Canandaigua, Tapestry Collection by Hilton
The Lake House on Canandaigua

The Lake House on Canandaigua

4.5 out of 5
770 South Main Street, Canandaigua, NY
$407 nightly
The price is $462 total per night from Oct 7 to Oct 8
$462 total
Oct 7 - Oct 8
Total with taxes and fees
9.2/10 Wonderful! (392 reviews)
Fabulous
"Fantastic in every way. Very highly recommend"

Reviewed on Sep 24, 2025

The Lake House on Canandaigua
See all 1,432 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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Frequently asked questions

How much does a Middlesex vacation package cost?
You can pick up a vacation package to this top destination from $538 on Expedia. However, how much your vacation to Middlesex costs will depend on the length of stay, season and hotel choice.
What are the cheapest months to go to Middlesex?
If you'd like to score a cheap Middlesex vacation package, consider traveling in October, November and December. You'll usually find lower prices on flights and hotels during these quieter months — perfect for budget-conscious travelers.
How many days is enough for Middlesex?
Generally, a handful of days is enough to check out the major sights during your Middlesex vacation. However, if you prefer to have more time to rest or go on day tours, think about extending your trip.
How to find the best Middlesex package deals?
Start your search for a Middlesex package deal by entering your destination and travel dates under our "Packages" tab. Then select a few filters, like "Property type" and "Amenities," to tailor the results to your exact style. You can also sort by "Package discount" and browse offers that come with big savings. If you don't find the perfect Middlesex 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 Middlesex escape underway.
Is it cheaper to book a Middlesex vacation as a package?
Expedia vacation packages are designed to make your money go further. Bundle your hotel, flight and car rental into one great-value price and you could save hundreds of dollars. You'll typically get a better deal than booking each component separately. And you'll still get the flexibility to create a personalized Middlesex vacation by choosing your favorite accommodation type, airline and car class.
When to book a vacation package to Middlesex?
Secure amazing discounts by reserving your flights in advance with Expedia. If spontaneity is more your thing, take advantage of our last-minute deals for a spur-of-the-moment Middlesex escape.
Does Expedia offer Book Now, Pay Later Middlesex vacation packages?
If you're like us, you love jet-setting around the world but don't love the big price tag that can sometimes come with it. That's why we offer Book Now, Pay Later vacations. With the help of online lender Affirm, you can break down the overall cost of your Middlesex vacation across 3, 6 or 12 months. There are also no hidden or late payment fees, so you can secure great vacation packages with payment plans as soon as you see them.

Explore a world of travel with Expedia

Explore a world of travel with Expedia

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