Winsted Vacations from $640

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to $2,000 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.
Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

4 out of 5
Downtown New Haven
Price was $757, price is now $640 per person
$640
per person
Dec 22 - Dec 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
8.6/10 Excellent! (1,105 reviews)

Landing Apartments New Haven Near Dixwell

Landing Apartments New Haven Near Dixwell

3 out of 5
Newhallville
Price was $939, price is now $786 per person
$786
per person
Dec 22 - Dec 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
2/10 (1 review)
The parking situation is very unclear. There is a small sign far from the lot that warns of towing but nothing in the area where you park. No significant warnings in communications with host.

Reviewed on May 25, 2026

Landing Furnished Apartment Near Yale University

Landing Furnished Apartment Near Yale University

3 out of 5
Downtown New Haven
Price was $777, price is now $672 per person
$672
per person
Dec 22 - Dec 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
2/10 (2 reviews)

Hyatus Luxury Residences City Crossing

Hyatus Luxury Residences City Crossing

4 out of 5
The Hill
Price was $1,095, price is now $950 per person
$950
per person
Dec 22 - Dec 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
9.2/10 Wonderful! (35 reviews)
Bed had no mattress cover but was very comfortable. Only one working lamp. Vents could use a good cleaning. I would recommend it and would stay again.

Reviewed on Oct 25, 2026

Luxury Furnished Apartments by Hyatus Downtown at Yale

Luxury Furnished Apartments by Hyatus Downtown at Yale

3.5 out of 5
The Hill
Price was $1,017, price is now $892 per person
$892
per person
Dec 22 - Dec 26
found 1 day ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
9.6/10 Exceptional! (91 reviews)
We stayed for a week and had a great trip, apartment was clean and cozy and the bathroom was very big. When we come back we will consider staying here again

Reviewed on Oct 26, 2026

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

Stay near popular Winsted attractions

Highland Lake

Highland Lake's crystal-clear waters span 445 acres across three bays, perfect for boating and fishing enthusiasts. Enjoy smallmouth bass fishing or kayak along Connecticut's scenic shoreline.
See properties

Winsted Hotel Deals

Enjoy a restful stay with fast internet, smart TV and the company of your pet.

Enjoy a restful stay with fast internet, smart TV and the company of your pet.

winsted CT
$179 nightly
The price is $204 total per night from Nov 3 to Nov 4
$204 total
Nov 3 - Nov 4
Total with taxes and fees
Enjoy a restful stay with fast internet, smart TV and the company of your pet.
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
$120 nightly
The price is $138 total per night from Nov 29 to Nov 30
$138 total
Nov 29 - Nov 30
Total with taxes and fees
DoubleTree by Hilton Hartford - Bradley Airport
Sheraton Hartford Hotel at Bradley Airport

Sheraton Hartford Hotel at Bradley Airport

3.5 out of 5
1 Bradley International Airport Windsor Locks CT
$212 nightly
The price is $243 total per night from Nov 8 to Nov 9
$243 total
Nov 8 - Nov 9
Total with taxes and fees
Sheraton Hartford Hotel at Bradley Airport
See all 840 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 $640 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.