Middlesex Vacations from $249

Book a Hotel + Flight or Car together to unlock savings

Photo by Matthew Jay

  • Plan, book, travel with confidence

  • Better together

    Save up to $1,045 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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 $315, price is now $249 per person
$249
per person
Jan 30 - Feb 1
found 1 day ago
Roundtrip flight included
New York (NYC) to Rochester (ROC)
9/10 Wonderful! (284 reviews)
Beds are so comfy and hotel is really upscale - overlooking beautiful Canandaigua Lake.

Reviewed on Dec 16, 2025

Hyatt Regency Rochester

Hyatt Regency Rochester

3.5 out of 5
Downtown Rochester
Price was $627, price is now $452 per person
$452
per person
Mar 5 - Mar 9
found 8 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Rochester (ROC)
7.4/10 Good! (1,005 reviews)
The staff was really nice and helpful. The room was not completely clean upon arrival.

Reviewed on Dec 16, 2025

DoubleTree by Hilton Rochester

DoubleTree by Hilton Rochester

4 out of 5
Price was $532, price is now $394 per person
$394
per person
Mar 5 - Mar 9
found 8 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Rochester (ROC)
7.8/10 Good! (1,002 reviews)
Half of the rooms have direct access to a beautiful six-story atrium garden. Renovations of guest rooms and are underway- definite improvements

Reviewed on Dec 22, 2025

The Strathallan Rochester Hotel & Spa - DoubleTree by Hilton

The Strathallan Rochester Hotel & Spa - DoubleTree by Hilton

4 out of 5
Downtown Rochester
Price was $615, price is now $478 per person
$478
per person
Mar 5 - Mar 9
found 8 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Rochester (ROC)
8.8/10 Excellent! (901 reviews)
We enjoyed our stay. Needed towels, staff brought up immediately after phone to desk. Bar was fun, too. We had dinner there and a few things. The price of the meals are extremely high, ie: pork chop was $46 which included no sides. The pork chop came out very under cooked, however the chef corrected and was very tasty. And the waitress Glacy (who was very fun to banter with!), made it right with a complimentary beer and dessert (which was very good). We would not eat there again onky because of the price, but again Service was excellent and the chef is talented. Overall, 8/10!

Reviewed on Dec 28, 2025

Oakfield Hotel & Suites, an Ascend Collection Hotel

Oakfield Hotel & Suites, an Ascend Collection Hotel

2.5 out of 5
Brighton
Price was $621, price is now $500 per person
$500
per person
Mar 5 - Mar 9
found 8 hours ago
Roundtrip non-stop flight included
San Juan (SJU) to Rochester (ROC)
9.2/10 Wonderful! (126 reviews)
Average stay compared to our 2 previous stays. Our tv glitched the entire time with poor viewing..

Reviewed on Dec 29, 2025

Don't see what you're looking for?
See all available trips from Columbus to Middlesex
View all trips

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

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
$254 nightly
The price is $289 total per night from Jan 22 to Jan 23
$289 total
Jan 22 - Jan 23, 2026
Total with taxes and fees
9.2/10 Wonderful! (435 reviews)
Clean, charming, and comfortable!

Reviewed on Dec 21, 2025

The Lake House on Canandaigua
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
$131 nightly
The price is $149 total per night from Jan 28 to Jan 29
$149 total
Jan 28 - Jan 29, 2026
Total with taxes and fees
8.8/10 Excellent! (301 reviews)
Beds are so comfy and hotel is really upscale - overlooking beautiful Canandaigua Lake.

Reviewed on Dec 16, 2025

Hotel Canandaigua, Tapestry Collection by Hilton
Plum Point Lodge

Plum Point Lodge

3 out of 5
3482 Plum Point Rd. South Himrod NY
$495 nightly
The price is $554 total per night from Jan 1 to Jan 2
$554 total
Jan 1 - Jan 2, 2026
Total with taxes and fees
9.2/10 Wonderful! (420 reviews)
Great location to everything fun. Nice staff. Good price.

Reviewed on Nov 30, 2025

Plum Point Lodge
See all 1,400 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

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Middlesex vacation package cost?
You can pick up a vacation package to this top destination from $249 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

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