Middlesex Vacations from $760

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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.
Hyatt Regency Rochester

Hyatt Regency Rochester

3.5 out of 5
Downtown Rochester
Price was $906, price is now $760 per person
$760
per person
May 15 - May 17
found 8 hours ago
Roundtrip flight included
Boston (BOS) to Rochester (ROC)
7.4/10 Good! (1,001 reviews)
Pool closed, one morning of no hot water, room above us was moving furniture all night long and due to the floor we heard everything.

Reviewed on Mar 29, 2026

Holiday Inn Express Rochester - Greece by IHG

Holiday Inn Express Rochester - Greece by IHG

2.5 out of 5
Price was $1,459, price is now $1,192 per person
$1,192
per person
Jun 21 - Jun 28
found 23 hours ago
Roundtrip non-stop flight included
Daytona Beach (DAB) to Rochester (ROC)
8.2/10 Very Good! (1,006 reviews)
Breakfast was ok. Not great but good. Biscuits and gravy was awesome, sausage good, omelette awful. OJ good. Lord of choices around hotel for food as well.

Reviewed on Mar 30, 2026

DoubleTree by Hilton Rochester

DoubleTree by Hilton Rochester

4 out of 5
Price was $1,479, price is now $1,210 per person
$1,210
per person
Jun 21 - Jun 28
found 23 hours ago
Roundtrip non-stop flight included
Daytona Beach (DAB) to Rochester (ROC)
7.8/10 Good! (1,009 reviews)
Literally 1 high chair for the whole property is crazy

Reviewed on Mar 29, 2026

Woodcliff Hotel and Spa

Woodcliff Hotel and Spa

4 out of 5
Price was $1,532, price is now $1,278 per person
$1,278
per person
Jun 21 - Jun 28
found 23 hours ago
Roundtrip non-stop flight included
Daytona Beach (DAB) to Rochester (ROC)
8.4/10 Very Good! (1,008 reviews)
Grounds are awesome, nice views & staff!

Reviewed on Mar 26, 2026

Holiday Inn Express Rochester - University Area by IHG

Holiday Inn Express Rochester - University Area by IHG

2.5 out of 5
Brighton
Price was $1,400, price is now $1,180 per person
$1,180
per person
Jun 21 - Jun 28
found 23 hours ago
Roundtrip non-stop flight included
Daytona Beach (DAB) to Rochester (ROC)
7.6/10 Good! (1,011 reviews)
It wasn't the worst hotel, so the things I say were not a deal breaker, just a small annoyance for me that was easily fixed. The toilet paper was low and there was no back up roll, so we had to ask for another. There was no body wash in the bottle, but we had soap with us. The hand soap ran out after a day of hand washing. There was only two of us. Staff in front office were nice and helpful. The cleaning staff was loud. Ample parking and area felt safe.

Reviewed on Mar 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
$308 nightly
The price is $350 total per night from Apr 9 to Apr 10
$350 total
Apr 9 - Apr 10
Total with taxes and fees
9.4/10 Exceptional! (463 reviews)
This was the second time we stayed overnight and have been to property for dinner separately too. This small resort is just the most quaint little spot in the finger lakes. We are local and love coming here for a little weekend relaxation and to celebrate 50th bdays. We were able to check in a little ...

Reviewed on Mar 23, 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 Apr 1 to Apr 2
$101 total
Apr 1 - Apr 2
Total with taxes and fees
8.2/10 Very Good! (1,086 reviews)
I had stayed here a few years back of course it was a little newer. they were working on the pool so we were not able to swim but the gym was awesome and clean We stopped at the restaurant in the morning to have breakfast staff was amazing the food was fresh and amazing I guess they make a lot of ...

Reviewed on Mar 24, 2026

41 Lakefront Hotel, Trademark Collection By Wyndham
Holiday Inn Express Canandaigua - Finger Lakes by IHG

Holiday Inn Express Canandaigua - Finger Lakes by IHG

2.5 out of 5
330 Eastern Blvd. Canandaigua NY
Fully refundable
$93 nightly
The price is $103 total per night from Apr 19 to Apr 20
$103 total
Apr 19 - Apr 20
Total with taxes and fees
8.6/10 Excellent! (1,004 reviews)
Comfortable, clean, quiet hotel.

Reviewed on Mar 26, 2026

Holiday Inn Express Canandaigua - Finger Lakes by IHG
See all 1,436 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 $760 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.