Winsted Vacations from $300

Book a Hotel + Flight or Car together to unlock savings

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.
Motel 6 Niantic, CT - New London

Motel 6 Niantic, CT - New London

2 out of 5
per person
Sep 22 - Sep 27
found 8 hours ago
Roundtrip flight included
Dallas (DFW) to New Haven (HVN)
7/10 Good! (1,000 reviews)
This is a no frills, quiet and clean place to stay.

Reviewed on Aug 1, 2025

Madison Beach Hotel

Madison Beach Hotel

4 out of 5
Madison Center
Save 100% on your flight
per person
Sep 22 - Sep 27
found 8 hours ago
Roundtrip flight included
Dallas (DFW) to New Haven (HVN)
9.4/10 Exceptional! (303 reviews)
The staff here is amazing along with the rooms and the property. This is a very nice and quiet place to stay with the family and they always seem to have some type of entertainment for the guests. Close to town and other points of interest. Only thing missing is a pool, but other than that this is a very nice place to stay.

Reviewed on Jul 12, 2025

Microtel Inn & Suites by Wyndham Uncasville Casino Area

Microtel Inn & Suites by Wyndham Uncasville Casino Area

2.5 out of 5
Save 100% on your flight
per person
Sep 22 - Sep 27
found 8 hours ago
Roundtrip flight included
Dallas (DFW) to New Haven (HVN)
8.8/10 Excellent! (1,735 reviews)
Very close to Mohegan sun. They have a shuttle service to and from the casino

Reviewed on Aug 2, 2025

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
per person
Oct 17 - Oct 21
found 10 hours ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
8.8/10 Excellent! (1,002 reviews)
NICE STAFF, GREEN HOTEL, GREAT BAR AND RESTAURANT.

Reviewed on Aug 1, 2025

Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

2.5 out of 5
per person
Oct 17 - Oct 21
found 3 hours ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
8.8/10 Excellent! (1,047 reviews)
I see lot of bugs in the room

Reviewed on Aug 2, 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

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
$110 nightly
The price is $127 total per night from Aug 25 to Aug 26
$127 total
Aug 25 - Aug 26
Total includes taxes and fees
8.8/10 Excellent! (1,100 reviews)
"Great beds and room for the price. Close to airport. Could have been cleaner."

Reviewed on Jul 28, 2025

Holiday Inn Express & Suites Bradley Airport by IHG
The Farmington Inn & Suites

The Farmington Inn & Suites

3 out of 5
827 Farmington Ave, Farmington, CT
Fully refundableReserve now, pay when you stay
$123 nightly
The price is $142 total per night from Aug 17 to Aug 18
$142 total
Aug 17 - Aug 18
Total includes taxes and fees
8.6/10 Excellent! (1,003 reviews)
"We loved it!"

Reviewed on Aug 1, 2025

The Farmington Inn & Suites
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
$135 nightly
The price is $155 total per night from Aug 15 to Aug 16
$155 total
Aug 15 - Aug 16
Total includes taxes and fees
8/10 Very Good! (1,003 reviews)
"We had a great time at the restaurant. Staff was wonderful, room was clean. But in room 307 the A/C unit sounds like a like a plane was in the room."

Reviewed on Jul 30, 2025

DoubleTree by Hilton Hartford - Bradley Airport
See all 803 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.

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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 $300 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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.