Winsted Vacations from $257

Book a Hotel + Flight or Car together to unlock savings

Photo by Kim Knox Beckius

  • Plan, book, travel with confidence

  • Better together

    Save up to $1,045 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

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.
Residence Inn by Marriott Southington

Residence Inn by Marriott Southington

3 out of 5
Price was $329, price is now $257 per person
$257
per person
Jan 16 - Jan 18
found 3 hours ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
17.2/10 Exceptional! (581 reviews)
A awesome place to stay whether just traveling through or staying in the area. Easy on and off the Interstate with lots of parking. A great staff from front desk to breakfast servers. Everyone made us feel at home. The rooms are spacious and feels like you are home not a hotel/motel/suite. Will definitely stay here again in the near future and recommend anyone traveling through to stop in and stay the night.

Reviewed on Nov 17, 2025

Residence Inn by Marriott Hartford/Windsor

Residence Inn by Marriott Hartford/Windsor

3 out of 5
Price was $369, price is now $295 per person
$295
per person
Feb 13 - Feb 16
found 3 hours ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
16.4/10 Exceptional! (656 reviews)
Clean, spacious room. Excellent service. Good breakfast

Reviewed on Nov 19, 2025

Hilton Garden Inn Hartford North/Bradley Int'l Airport

Hilton Garden Inn Hartford North/Bradley Int'l Airport

3 out of 5
Price was $399, price is now $321 per person
$321
per person
Feb 13 - Feb 16
found 3 hours ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
17.6/10 Exceptional! (1,004 reviews)
This hotel was clean which was great because I booked the wrong hotel I thought this was the one I stayed at before but it was the Marriott across from it. I was glad that it ended up being clean or I probably would’ve asked to cancel my reservation because this is the second Hilton. I’ve stayed in and they are so dated. It’s sad like spend some money and fix them up because you would think you’re booking at a Hilton and it should be nice and literally they’re old and rundown and it’s very sad. The only reason why I gave a four star for cleanliness was because it was clean. If you are looking for a nice bougie hotel room and hotel, this is not the place book across the street at the Marriott or the Hyatt.

Reviewed on Nov 24, 2025

Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

2.5 out of 5
Price was $445, price is now $358 per person
$358
per person
Jan 31 - Feb 3
found 1 day ago
Roundtrip non-stop flight included
San Juan (SJU) to New Haven (HVN)
17.2/10 Exceptional! (1,149 reviews)
The rooms are nice and the staff is accommodating. The fitness center could use an upgrade

Reviewed on Nov 22, 2025

Cambria Hotel Manchester South Windsor

Cambria Hotel Manchester South Windsor

3 out of 5
Price was $483, price is now $398 per person
$398
per person
Feb 13 - Feb 16
found 3 hours ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
18.4/10 Exceptional! (828 reviews)
Everything was great

Reviewed on Nov 17, 2025

Don't see what you're looking for?
See all available trips from Columbus to Winsted
View all trips

Black Friday Sale

Limited-time deals: Save up to 50% on select hotels.
Book now

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
$95 nightly
The price is $109 total per night from Dec 5 to Dec 6
$109 total
Dec 5 - Dec 6
Total with taxes and fees
7.8/10 Good! (999 reviews)
Staff was very courteous. Room was very clean. Loved it. Will definitely be back.

Reviewed on Nov 15, 2025

Extended Stay America Suites Hartford Farmington
Sheraton Hartford Hotel at Bradley Airport

Sheraton Hartford Hotel at Bradley Airport

3.5 out of 5
1 Bradley International Airport Windsor Locks CT
Fully refundableReserve now, pay when you stay
$229 nightly
The price is $263 total per night from Dec 12 to Dec 13
$263 total
Dec 12 - Dec 13
Total with taxes and fees
9/10 Wonderful! (1,008 reviews)
Ordered room service and it came very quickly. Hotel is under renovation and is very nice. Will say that walls are not well insulated because you can hear a lot of what’s going on in other rooms.

Reviewed on Nov 19, 2025

Sheraton Hartford Hotel at 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
$103 nightly
The price is $119 total per night from Dec 18 to Dec 19
$119 total
Dec 18 - Dec 19
Total with taxes and fees
8.8/10 Excellent! (1,150 reviews)
Great

Reviewed on Nov 19, 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.

Find the Best Winsted Vacation Packages

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

More vacations you might like

All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Kid Friendly Vacations
Kid Friendly Vacations

Frequently asked questions

How much does a Winsted vacation package cost?
You can snap up a vacation package to this top destination from $257 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.