Winchester Vacations from $443

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Your Winchester Vacation

The best way to experience this unique city is with a tailor-made Winchester vacation package. Base yourself in the neighborhood of New Hartford, which is good for nature, history and skiing or choose someplace else — our package deals are all about you. Make your trip to Winchester even more enjoyable by going sightseeing. Highland Lake, Laurel Lanes and Winchester Historical Society are some of the leading attractions you'll want to explore. Whatever your travel plans or budget, organizing your ultimate tailored Winchester vacation is easy with Expedia.

The Latest Winchester vacation packages

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

2.5 out of 5
Save 100% on your flight
Price was $618, price is now $443 per person
$443
per person
Dec 7 - Dec 14
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to New Haven (HVN)
8.8/10 Excellent! (1,092 reviews)
excellent hotel,room clean and excellent service.

Reviewed on Sep 28, 2025

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
Save 100% on your flight
Price was $1,753, price is now $1,020 per person
$1,020
per person
Dec 12 - Dec 15
found 11 hours ago
Roundtrip flight included
Tampa (TPA) to New Haven (HVN)
No reviews
Hilton Garden Inn Hartford North/Bradley Int'l Airport

Hilton Garden Inn Hartford North/Bradley Int'l Airport

3 out of 5
Save 100% on your flight
Price was $772, price is now $551 per person
$551
per person
Dec 7 - Dec 14
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to New Haven (HVN)
8.8/10 Excellent! (1,005 reviews)
Convenient to airport. Stayed overnight for a flight. Hotel is as expected. Staff at check in was a bit difficult to understand with hearing issues. One slight issue with our room key not working but otherwise would stay again in the future for airport closeness.

Reviewed on Sep 22, 2025

Residence Inn by Marriott Southington

Residence Inn by Marriott Southington

3 out of 5
Save 100% on your flight
Price was $880, price is now $672 per person
$672
per person
Dec 7 - Dec 14
found 1 day ago
Roundtrip non-stop flight included
Orlando (MCO) to New Haven (HVN)
8.6/10 Excellent! (570 reviews)
It was a perfect place to stay for a wedding weekend. Great family and dog friendly accommodations.

Reviewed on Sep 30, 2025

Madison Beach Hotel

Madison Beach Hotel

4 out of 5
Madison Center
Price was $1,029, price is now $831 per person
$831
per person
Dec 10 - Dec 13
found 5 hours ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
9.4/10 Exceptional! (316 reviews)
the staff was exceptional and our dinner was very good

Reviewed on Sep 17, 2025

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Discover the most popular places to visit in Winchester

Winchester Historical Society

You can spend an afternoon exploring the galleries in Winchester Historical Society during your trip to Winchester. Take in the live music in this relaxing area.

Winchester Historical Society

Winchester Hotel Deals

Extended Stay America Suites Hartford Farmington

Extended Stay America Suites Hartford Farmington

2.5 out of 5
1 Batterson Park Rd, Farmington, CT
Fully refundableReserve now, pay when you stay
$107 nightly
The price is $123 total per night from Oct 12 to Oct 13
$123 total
Oct 12 - Oct 13
Total with taxes and fees
7.8/10 Good! (1,013 reviews)
"Ac made noise in the middle of the night, i shut it off."

Reviewed on Sep 24, 2025

Extended Stay America Suites Hartford Farmington
Avon Old Farms Hotel

Avon Old Farms Hotel

3.5 out of 5
279 Avon Mountain Rd, Avon, CT
Fully refundableReserve now, pay when you stay
$149 nightly
The price is $171 total per night from Oct 13 to Oct 14
$171 total
Oct 13 - Oct 14
Total with taxes and fees
8.2/10 Very Good! (1,000 reviews)
Disappointed
"Stay was good until my boyfriend fell due to a long tablecloth draped on the floor about 6 inches and hitting his head on another table. Minimum aid given and no offer for compensation of any sort. Our prior stay back in May had been wonderful."

Reviewed on Sep 8, 2025

Avon Old Farms Hotel
The Farmington Inn & Suites

The Farmington Inn & Suites

3 out of 5
827 Farmington Ave, Farmington, CT
Fully refundableReserve now, pay when you stay
$144 nightly
The price is $166 total per night from Oct 2 to Oct 3
$166 total
Oct 2 - Oct 3
Total with taxes and fees
8.6/10 Excellent! (1,002 reviews)
"Great staff, very helpful. Good location."

Reviewed on Sep 25, 2025

The Farmington Inn & Suites
See all 675 properties in Winchester
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 Winchester vacation package cost?
You'll find cheap prices from $443 on Expedia for your Winchester escape. However, factors like the hotel choice, length of stay and season will determine how much your vacation to Winchester costs.
What are the cheapest months to go to Winchester?
November, December and January are the best times to search for cheap Winchester vacation packages. Traveling in less busy months means you can typically find lower prices on accommodations and flights.
How many days is enough for Winchester?
The ideal duration for your Winchester vacation depends on what you'd like to do. Generally, a handful of days to a week will give you enough time to go to all the main attractions and explore some hidden gems along the way.
How to find the best Winchester package deals?
Use Expedia's filters to help you find some great Winchester package deals. When you begin your search, just set your maximum budget and then order the results by "Price: low to high." If you're looking to save, plan your adventure for midweek, or look for Winchester package deals in the off-season. Play around with your travel dates and you may land even bigger discounts. As a rule of thumb, it's usually best to book your vacation package well in advance.
Is it cheaper to book a Winchester 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 enjoy significant savings. You'll generally score a better deal than booking each component separately. And you'll still have the freedom to create a customized Winchester vacation by choosing your favorite airline, accommodation type and car class.
When to book a vacation package to Winchester?
If you've got your Winchester travel dates locked in, book as early as you can to bag some terrific deals. With Expedia, you can often reserve some flights up to one year in advance. Prefer spur-of-the-moment adventures? Our last-minute deals are great for quick escapes.
Does Expedia offer Book Now, Pay Later Winchester vacation packages?
Your Winchester getaway should be a relaxing escape from your daily routine, not a reason for money-related stress. So to allow you more flexibility, we've joined up with online lender Affirm to bring you our Book Now, Pay Later vacations. Choose one of our vacation packages with payment plans and spread the total cost over 3, 6 or 12 months. Plus, there are no late payment fees or hidden costs to worry about.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.