Middlesex Vacations from $466

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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 $579, price is now $466 per person
$466
per person
Mar 19 - Mar 22
found 1 day ago
Roundtrip flight included
Newark Liberty Intl. Airport (EWR) to Rochester (ROC)
9/10 Wonderful! (284 reviews)
Everything was great

Reviewed on Feb 5, 2026

The Strathallan Rochester Hotel & Spa - DoubleTree by Hilton

The Strathallan Rochester Hotel & Spa - DoubleTree by Hilton

4 out of 5
Downtown Rochester
Price was $988, price is now $730 per person
$730
per person
May 7 - May 10
found 12 hours ago
Roundtrip flight included
New York (NYC) to Rochester (ROC)
8.8/10 Excellent! (901 reviews)
There was construction on several floors including the main lobby . The room was new and was amazing . Other than that was a good stay

Reviewed on Jan 21, 2026

Hyatt Regency Rochester

Hyatt Regency Rochester

3.5 out of 5
Downtown Rochester
Price was $757, price is now $562 per person
$562
per person
May 7 - May 10
found 12 hours ago
Roundtrip flight included
New York (NYC) to Rochester (ROC)
7.4/10 Good! (1,005 reviews)
Room was in great condition. Restaurants and coffee shop are awful .

Reviewed on Feb 10, 2026

Hampton Inn & Suites Rochester/Victor

Hampton Inn & Suites Rochester/Victor

2.5 out of 5
Price was $710, price is now $594 per person
$594
per person
May 7 - May 10
found 12 hours ago
Roundtrip flight included
New York (NYC) to Rochester (ROC)
9/10 Wonderful! (1,001 reviews)
The first room was too hot from a faulty thermostat, but they were able to get me another room without issue. The 2nd room had a good amount of wear and tear. Some of the furniture is dated as well. Overall, the stay was clean and a good value for the price.

Reviewed on Feb 6, 2026

The Lake House on Canandaigua

The Lake House on Canandaigua

4.5 out of 5
Price was $945, price is now $796 per person
$796
per person
May 7 - May 10
found 12 hours ago
Roundtrip flight included
New York (NYC) to Rochester (ROC)
9.4/10 Exceptional! (422 reviews)
The staff was friendly and it was a unique and cozy place to stay. 4 stars because sadly one of the main things we came for was the advertised all year round outdoor headed pool. The pool was not heated as advertised and it had a cover on it. Bummer as I thought that was a unique offering but aside from that we enjoyed our stay and the amenities.

Reviewed on Jan 30, 2026

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Discover the most popular places to visit in Middlesex

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

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
$273 nightly
The price is $310 total per night from Feb 26 to Feb 27
$310 total
Feb 26 - Feb 27
Total with taxes and fees
9.2/10 Wonderful! (452 reviews)
Everything was amazing!

Reviewed on Feb 2, 2026

The Lake House on Canandaigua
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
$89 nightly
The price is $101 total per night from Feb 15 to Feb 16
$101 total
Feb 15 - Feb 16
Total with taxes and fees
8.2/10 Very Good! (1,076 reviews)
Clean room and great mattress!

Reviewed on Feb 9, 2026

41 Lakefront Hotel, Trademark Collection By Wyndham
Microtel Inn & Suites by Wyndham Geneva

Microtel Inn & Suites by Wyndham Geneva

2 out of 5
550 Hamilton St Geneva NY
Fully refundableReserve now, pay when you stay
$77 nightly
The price is $85 total per night from Feb 17 to Feb 18
$85 total
Feb 17 - Feb 18
Total with taxes and fees
8.4/10 Very Good! (1,003 reviews)
Friendly staff,clean room

Reviewed on Jan 30, 2026

Microtel Inn & Suites by Wyndham Geneva
See all 1,425 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.

Find the Best Middlesex Vacation Packages

Middlesex Essential Information

Language
English
Currency
U.S dollars
Top Sights
Keuka Lake State Park, Hunt Country Vineyards and Clarks Gully

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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 $466 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.

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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.