Middlesex Vacations from $549
Book a Hotel + Flight or Car together to unlock savings
- Plan, book, travel with confidence
- Better togetherSave up to $2,000 when you book a flight and hotel together*
- Find the right fitWith over 300,000 hotels worldwide, it's easy to create a perfect package
- Rest easyPlan, 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.
Hyatt Regency Rochester
Downtown Rochester
$613
per person
Dec 18 - Dec 24
found 15 hours ago
Roundtrip flight included
New York (NYC) to Rochester (ROC)
7.4/10 Good! (1,005 reviews)
Room surfaces were small. Ice was inconveniently located. The fitness room equipment was poor. Parking was convenient. Staff was helpful. Overall a mixed bag.
Reviewed on Sep 28, 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
$143 nightly
$162 total
Oct 26 - Oct 27
Total with taxes and fees
The Lake House on Canandaigua
770 South Main Street Canandaigua NY
$314 nightly
$356 total
Oct 27 - Oct 28
Total with taxes and fees
Microtel by Wyndham Penn Yan Finger Lakes Region
124 Elm St Penn Yan NY
$101 nightly
$113 total
Oct 29 - Oct 30
Total with taxes and fees
8.8/10 Excellent! (1,000 reviews)
"Breakfast was great. Staff was very polite and professional."
Reviewed on Sep 29, 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 |
More vacations you might like
Frequently asked questions
How much does a Middlesex vacation package cost?
You can pick up a vacation package to this top destination from $549 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
- Marriott Hotels & Resorts Hotels in Canandaigua
- Guesthouses in Middlesex
- Hotels in Keuka Park
- Independent Hotels in Bristol Harbour Village
- Lake in Canandaigua
- Motels in Middlesex
- Hotels in Middlesex
- Hotels in Penn Yan
- Apartments in Canandaigua
- Budget in Canandaigua
- Cabins in Naples
- 5 Star Hotels in Penn Yan
- Hotels in Canandaigua
- 4 Star Hotels in Middlesex
- Hotels in Naples
- Flights to Canandaigua
- Flights to Finger Lakes Region
- Delta Air Lines Atlanta (ATL) to Rochester (ROC) flights
- Flights to Naples
- Flights to Keuka Park
- Flights from Boston (BOS) to Rochester (ROC)
- Flights to Geneva
- Flights to Penn Yan
- Flights from Jamaica (JFK) to Rochester (ROC)
- JetBlue Airways Jamaica (JFK) to Rochester (ROC) flights
- Visit Canandaigua
- Finger Lakes Region All Inclusive Vacation Packages
- Where to stay in Fairport
- Where to stay in Canandaigua
- Visit Honeoye
- Visit Penn Yan
- Bristol Mountain Ski Resort
- Seneca Lake
- Finger Lakes Region All Inclusive Vacation Packages
- Finger Lakes Region All Inclusive Vacation Packages
- Where to stay in Rochester
- Finger Lakes Region All Inclusive Vacation Packages
- Where to stay in Finger Lakes Region
- Palmyra Vacations
- Manchester Vacations
- Visit Branchport
- Finger Lakes Region All Inclusive Vacation Packages
- Brighton Vacations
- Finger Lakes Region All Inclusive Vacation Packages
- Finger Lakes Region All Inclusive Vacation Packages
- Visit Naples
- Where to stay in Penn Yan
- Naples Vacations
- Visit Finger Lakes Region
- Where to stay in Hornell
- Hector Vacations
- Rochester Vacations
- Where to stay in Victor
- Canandaigua Vacations
- Finger Lakes Region All Inclusive Vacation Packages
- Keuka Lake State Park
- The Windmill Farm
- Finger Lakes Region All Inclusive Vacation Packages
- Where to stay in Geneva
- Visit Seneca Falls
- Where to stay in Ovid
- Corning Vacations
- Visit Farmington
- Visit Himrod
- Finger Lakes Region All Inclusive Vacation Packages
- Victor Vacations
- Where to stay in Waterloo
- Visit Geneva
- Watkins Glen Vacations
- Car rentals in Canandaigua
- Car rentals in Keuka Park
- Hertz Rental Cars in Penn Yan
- Car rentals in Prattsburgh
- Luxury Car Rentals in Canandaigua
- Van Car Rentals in Penn Yan
- Car rentals in Middlesex
- Enterprise Rental Cars in Canandaigua
- Car rentals in Naples
- Car rentals in Penn Yan
- Avis Rental Cars in Canandaigua
- Pickup Car Rentals in Penn Yan
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
