Middlesex Vacations from $710
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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.
Sutherland House Victorian Bed & Breakfast
$710
per person
Sep 26 - Sep 28
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Rochester (ROC)
9.8/10 Exceptional! (169 reviews)
My husband and I had a wonderful time there. We had a room with a whirlpool bath, which is very pleasant. The room was very clean and the bed very comfortable. The property is very well maintained and very pretty. We really appreciated the attention to detail in the different parts of the house that we passed through. The breakfast was delicious and served with great kindness. I thank the owners for the quality of the stay we spent and highly recommend this beautiful property.
Reviewed on Aug 13, 2026
School 31 Lofts at Colors Studios
Downtown Rochester
$1,089
per person
Sep 23 - Sep 30
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to Rochester (ROC)
8.8/10 Excellent! (586 reviews)
Room was nice, old details are whimsical. Bathroom was open to the room, but OK if you know each other!
Reviewed on Aug 14, 2026
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.
Middlesex Hotel Deals
41 Lakefront Hotel, Trademark Collection By Wyndham
41 Lake Front Blvd Geneva NY
$125 nightly
$142 total
Sep 7 - Sep 8
Total with taxes and fees
The Lake House on Canandaigua
770 South Main Street Canandaigua NY
$350 nightly
$397 total
Sep 14 - Sep 15
Total with taxes and fees
9.4/10 Exceptional! (547 reviews)
"Everyone & everything was amazing! Keep doing what you are doing."
Reviewed on Aug 15, 2026
Microtel by Wyndham Penn Yan Finger Lakes Region
124 Elm St Penn Yan NY
Fully refundableReserve now, pay when you stay
$122 nightly
$137 total
Aug 23 - Aug 24
Total with taxes and fees
8.8/10 Excellent! (1,006 reviews)
"They need to hire a person to handle the breakfast times. Instead of having the front desk staff do it"
Reviewed on Aug 15, 2026
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 $710 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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- Lacey Magruder Winery
- Bristol Mountain Ski Resort
- Majestic Hills Golf Course
- Sonnenberg Gardens and Mansion State Historic Park
- Naples Vacations
- Vintage Tracks Museum
- Oliver House Museum
- Sandy Bottom Park
- Torrey Ridge Winery
- Hobart and William Smith Colleges
- Visit Middlesex
- The Windmill Farm & Craft Market
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- Heron Hill Winery Tasting Room at Bristol
- Fox Run Vineyards
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- Roseland Waterpark
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- Keuka College
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- Visit Seneca Falls
- Mcgregor Vineyard
- Keuka Lake State Park
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
