Middlesex Holidays
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Top hotels in Middlesex
41 Lakefront Hotel, Trademark Collection By Wyndham
41 Lake Front Blvd Geneva NY
Fully refundableReserve now, pay when you stay
S$182
7 Sept - 8 Sept
includes taxes & fees
8.2/10 Very good! (1,181 reviews)
"I was very disappointed with our stay...there was seagull feathers and poop everywhere. Our room was not good, the bed was hard, the base of the bed was torn and tattered,the bathroom was handicap accessible and the seat was moldy, tile was moldy and the shower was hand held and sprayed all over ..."
Reviewed on 12 Aug, 2026
The Lake House on Canandaigua
770 South Main Street Canandaigua NY
Fully refundableReserve now, pay when you stay
S$519
13 Sept - 14 Sept
includes taxes & fees
9.4/10 Exceptional! (544 reviews)
"The viewing areas to the lake were wonderful. The food was fantastic."
Reviewed on 11 Aug, 2026
Microtel by Wyndham Penn Yan Finger Lakes Region
124 Elm St Penn Yan NY
Fully refundableReserve now, pay when you stay
S$175
31 Aug - 1 Sept
includes taxes & fees
8.8/10 Excellent! (1,002 reviews)
"Hotel rooms are clean but could use updating"
Reviewed on 12 Aug, 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.
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.
Frequently asked questions
How much does a Middlesex holiday package cost?
You can pick up a holiday package to this top destination on Expedia. However, how much your holiday to Middlesex costs will depend on the length of stay, season and hotel choice.
What are the cheapest months to go to Middlesex?
You can generally find reduced prices and greater availability in January, February and March. Browse our cheap Middlesex holiday packages and you could land some great off-season deals.
How many days is enough for Middlesex?
Usually, a handful of days is enough to tick off the major sights during your Middlesex holiday. But if you want to have more time to unwind or take day trips, 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 holiday as a package?
Expedia holiday 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 personalised Middlesex holiday by choosing your favourite accommodation type, airline and car class.
When to book a holiday 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.
How to plan a trip to Middlesex?
- Choose when to go: Check your schedule and pack your bags. Your favourite season and the type of activities available will also help you decide when to visit Middlesex.
- Set a budget: Factor in expenses like flights, food and transportation when working out how much to set aside for your trip to Middlesex. Then, pick a property that suits your budget, whether that's a low-cost option or a deluxe getaway.
- Work out your trip length: Consider how long you want to spend discovering Middlesex. Plan your days so you can get to all the attractions and activities you're interested in without rushing.
- Bundle your bookings: With your travel dates in order, you can combine your flights, car rental, hotels and more into a customised Middlesex holiday package.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.
