A pier with a red lighthouse at dusk, reflecting on calm water.

Middlesex Vacations from $465

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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

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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.

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    Middlesex Hotel Deals

    Hampton Inn Penn Yan

    An outdoor patio with tables and chairs, overlooking a lake.
    • Address: 110 Mace Street, Penn Yan, NY, 14527, US
    • Location: 11.5 mi from Middlesex
    • Star rating: 2.5/5
    • Guest rating: 9.4/10 (Exceptional, 1002 reviews)
    • Price: $81 nightly, $90 total, Dec 6 - Dec 7, Total with taxes and fees
    • Review: Room couch smelled like urine Checked out a day earlier with no credit.

    Best Western Plus Vineyard Inn & Suites

    A Best Western Plus hotel with a covered entrance, multiple windows, and a brick facade.
    • Address: 142 Lake St, Penn Yan, NY, 14527, US
    • Location: 11.7 mi from Middlesex
    • Star rating: 2.5/5
    • Guest rating: 9.6/10 (Exceptional, 1007 reviews)
    • Price: $85 nightly, $95 total, Dec 7 - Dec 8, Total with taxes and fees

    Microtel by Wyndham Penn Yan Finger Lakes Region

    A hotel entrance with a covered walkway, brick pillars, and a central entrance with glass doors.
    • Address: 124 Elm St, Penn Yan, NY, 14527, US
    • Location: 11.6 mi from Middlesex
    • Star rating: 3/5
    • Guest rating: 8.8/10 (Excellent, 1005 reviews)
    • Price: $79 nightly, $89 total, Dec 6 - Dec 7, Total with taxes and fees

    The Mansion at Keuka Lake

    A large building with a grand entrance, multiple balconies, and a flagpole with an American flag.
    • Address: 3456 New York 54A, Keuka Park, NY, 14478, US
    • Location: 10.4 mi from Middlesex
    • Star rating: 3.5/5
    • Guest rating: 9.6/10 (Exceptional, 34 reviews)
    • Price: $83 nightly, $93 total, Nov 15 - Nov 16, Total with taxes and fees
    • Review: We had a lovely stay!

    Holiday Inn Express Canandaigua - Finger Lakes by IHG

    A modern living room with a stone fireplace, a glass coffee table, and two sofas.
    • Address: 330 Eastern Blvd., Canandaigua, NY, 14424, US
    • Location: 12 mi from Middlesex
    • Star rating: 2.5/5
    • Guest rating: 8.6/10 (Excellent, 1000 reviews)
    • Price: $125 nightly, $138 total, Nov 18 - Nov 19, Total with taxes and fees
    • Review: Good

    Fairfield Inn & Suites by Marriott Geneva Finger Lakes

    A modern living room with a stone fireplace, a sofa, a coffee table, and a TV area.
    • Address: 383 Hamilton St, Geneva, NY, 14456, US
    • Location: 17.6 mi from Middlesex
    • Star rating: 3/5
    • Guest rating: 9.2/10 (Wonderful, 699 reviews)
    • Price: $107 nightly, $122 total, Nov 22 - Nov 23, Total with taxes and fees
    • Review: Great hotel with a great breakfast and staff. Clean and spacious rooms with all the comfort.

    Hotel Canandaigua, Tapestry Collection by Hilton

    A grassy area with two Adirondack chairs, a picnic table, and a view of a lake with boats and a distant shoreline.
    • Address: 205 Lakeshore Drive, Canandaigua, NY, 14424, US
    • Location: 11.7 mi from Middlesex
    • Star rating: 3.5/5
    • Guest rating: 9/10 (Wonderful, 501 reviews)
    • Price: $143 nightly, $162 total, Nov 22 - Nov 23, Total with taxes and fees

    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 $465 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.