Winsted Vacations from $293

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Your Winsted Vacation

The easiest way to experience this vibrant city is with a customized Winsted vacation package. Stay in the neighborhood of New Hartford, which is great for nature, history and skiing or choose someplace else — our package deals are all about you. If your trip to Winsted includes a little sightseeing, drop by major attractions such as Highland Lake, Jerram Winery and Laurel Lanes. Whoever you're going away with and whatever you plan to spend, your ultimate Winsted vacation is just clicks away with Expedia.

The Latest Winsted vacation packages

Price found within the past 48 hours. Click for updated prices.
Graduate by Hilton New Haven

Graduate by Hilton New Haven

4 out of 5
Downtown New Haven
Price was $373, price is now $293 per person
$293
per person
Nov 16 - Nov 18
found 24 hours ago
Roundtrip non-stop flight included
Tampa (TPA) to New Haven (HVN)
9.2/10 Wonderful! (877 reviews)
Really creative and thoughtful design with themed tiles, artwork, etc. makes this hotel a lot of fun as well as convenient and comfortable. The high ceilings, large bathroom for a old (remodeled) buildings, and other nice touches were pleasant surprises. It's very close to Yale and plenty of restaurants.

Reviewed on Oct 9, 2025

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
Save 100% on your flight
Price was $1,503, price is now $862 per person
$862
per person
Dec 10 - Dec 13
found 18 hours ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
No reviews
Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

2.5 out of 5
Price was $673, price is now $486 per person
$486
per person
Dec 23 - Dec 30
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
8.8/10 Excellent! (1,092 reviews)
Nice but aged. Back parking lot always seemed to have people hanging out in/around their vehicles and back door stated it was secure 24 hrs but was always propped open or unlocked when we entered over span of 4 days, even at night

Reviewed on Oct 9, 2025

Residence Inn by Marriott Southington

Residence Inn by Marriott Southington

3 out of 5
Price was $712, price is now $527 per person
$527
per person
Dec 23 - Dec 30
found 1 day ago
Roundtrip 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

Days Inn by Wyndham Ridgefield

Days Inn by Wyndham Ridgefield

2 out of 5
Price was $691, price is now $545 per person
$545
per person
Nov 24 - Dec 1
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
5.8/10 (875 reviews)
The room was pretty shabby- with wood peeking through the carpet. No shampoos or other standard conveniences.

Reviewed on Sep 22, 2025

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Discover the most popular places to visit in Winsted

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

Winsted 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
$102 nightly
The price is $117 total per night from Nov 2 to Nov 3
$117 total
Nov 2 - Nov 3
Total with taxes and fees
7.8/10 Good! (1,006 reviews)
"I loved my spacious room, kitchen facilities, comfy bed, easy parking. The staff was friendly and helpful, but what I liked best was the feeling of being in my own space, not a hotel."

Reviewed on Oct 6, 2025

Extended Stay America Suites Hartford Farmington
DoubleTree by Hilton Hartford - Bradley Airport

DoubleTree by Hilton Hartford - Bradley Airport

4 out of 5
16 Ella T. Grasso Turnpike, Windsor Locks, CT
Fully refundableReserve now, pay when you stay
$122 nightly
The price is $141 total per night from Oct 19 to Oct 20
$141 total
Oct 19 - Oct 20
Total with taxes and fees
8/10 Very Good! (1,003 reviews)
"Felt like I was in a car lot"

Reviewed on Oct 5, 2025

DoubleTree by Hilton Hartford - Bradley Airport
Holiday Inn Express & Suites Bradley Airport by IHG

Holiday Inn Express & Suites Bradley Airport by IHG

2.5 out of 5
600 Spring St, Windsor Locks, CT
Fully refundable
$105 nightly
The price is $121 total per night from Oct 30 to Oct 31
$121 total
Oct 30 - Oct 31
Total with taxes and fees
8.8/10 Excellent! (1,133 reviews)
Comfortable
"Parking lot was nice and big"

Reviewed on Sep 30, 2025

Holiday Inn Express & Suites Bradley Airport by IHG
See all 809 properties in Winsted
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.

Winsted Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Bradley Intl. Airport (BDL)
Population
7,700
Top Sights
Connecticut Valley Winery, Winchester Historical Society and Jerram Winery

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Frequently asked questions

How much does a Winsted vacation package cost?
You can snap up a vacation package to this top destination from $293 on Expedia. However, how much your vacation to Winsted costs will depend on the length of stay, season and hotel choice.
What are the cheapest months to go to Winsted?
November, December and January are great times to look for cheap Winsted vacation packages. Opting to travel in less busy months means you can usually find lower prices on hotels and flights.
How many days is enough for Winsted?
Allow around 3 days for your Winsted vacation in order to take in all that makes this destination unique. Stroll around popular neighborhoods, including Winchester and West Hill Lake. Then tick off top attractions such as Winchester Historical Society and Highland Lake. With a well-organized itinerary, you can keep busy with room for some relaxation too. Want to go beyond Winsted? Consider fitting in a day trip or two.
Is it worth booking a vacation package to Winsted?
Whether you're planning to visit attractions like Highland Lake and Laurel Lanes, or eager to experience its top-notch nature and culture, a Winsted vacation guarantees an unforgettable adventure. Book your getaway with Expedia and discover why Winsted is such a good vacation destination.
How to find the best Winsted package deals?
Use Expedia's handy filters to help you find some fabulous Winsted package deals. When you start your search, just set your maximum budget and then sort the results by "Price: low to high." If you're looking to save, plan your escape for midweek, or search for Winsted package deals in the off-season. Switch up your travel dates and you may score even bigger discounts. As a rule of thumb, it's typically best to lock in your vacation package well in advance.
Is it cheaper to book a Winsted vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your hotel, flight and car rental into one great-value price and enjoy significant savings. You'll generally get a better deal than booking each component separately. And you'll still get the flexibility to create a personalized Winsted vacation by choosing your favorite airline, accommodation type and car class.
When to book a vacation package to Winsted?
If you have your Winsted travel dates confirmed, book early to score some terrific deals. With Expedia, you can typically reserve some flights up to one year ahead of time. Prefer spur-of-the-moment trips? Our last-minute deals are great for jetting off on a whim.
Does Expedia offer Book Now, Pay Later Winsted vacation packages?
Secure your perfect escape to Winsted with help from our Book Now, Pay Later vacations. There's no need to scrimp and save or wait until your next paycheck — we've joined forces with online lender Affirm to offer you flexibility with your finances. Our vacation packages with payment plans allow you to spread the total cost across 3, 6 or 12 months. With no late payment fees or hidden charges, it's a breeze to stay on budget and snap up travel deals while they last.

Explore a world of travel with Expedia

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.