Winsted Vacations from $160

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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.
Motel 6 New Haven - Branford, CT

Motel 6 New Haven - Branford, CT

2 out of 5
Price was $199, price is now $160 per person
$160
per person
Feb 26 - Mar 1
found 23 hours ago
Roundtrip flight included
Miami (MIA) to New Haven (HVN)
7/10 Good! (1,001 reviews)
The man the helped check me in was super nice. I picked this place because i had an 8am flight & it was very close to the airport. Also the rate was reasonable. The room next door had loud music playing, so i called the front desk. Within 10 - 15 min they turned it down.

Reviewed on Dec 2, 2025

Landing Modern 2bd, Gym

3 out of 5
West New Haven
Save 100% on your flight
Price was $522, price is now $377 per person
$377
per person
Feb 26 - Mar 1
found 23 hours ago
Roundtrip flight included
Miami (MIA) to New Haven (HVN)
No reviews
Madison Beach Hotel

Madison Beach Hotel

4 out of 5
Madison Center
Save 100% on your flight
Price was $728, price is now $536 per person
$536
per person
Feb 26 - Mar 1
found 23 hours ago
Roundtrip flight included
Miami (MIA) to New Haven (HVN)
9.4/10 Exceptional! (336 reviews)
beautiful room and views

Reviewed on Dec 13, 2025

Cambria Hotel New Haven University Area

Cambria Hotel New Haven University Area

3 out of 5
West River
Save 100% on your flight
Price was $278, price is now $208 per person
$208
per person
Feb 26 - Mar 1
found 23 hours ago
Roundtrip flight included
Miami (MIA) to New Haven (HVN)
8.8/10 Excellent! (966 reviews)
The room was nice and the staff seemed friendly.

Reviewed on Jan 8, 2026

Heritage Hotel, Golf, Spa & Conference Center, BW Premier Collection

Heritage Hotel, Golf, Spa & Conference Center, BW Premier Collection

3.5 out of 5
Price was $287, price is now $237 per person
$237
per person
Feb 26 - Mar 1
found 23 hours ago
Roundtrip flight included
Miami (MIA) to New Haven (HVN)
8.4/10 Very Good! (1,004 reviews)
Very nice, staff were excellent.

Reviewed on Jan 8, 2026

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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

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 Jan 30 to Jan 31
$263 total
Jan 30 - Jan 31
Total with taxes and fees
9/10 Wonderful! (1,013 reviews)
I arrived at 2 am and front desk was able to get me into a room at a great rate so I could get a few hours of sleep. Thank you!

Reviewed on Jan 4, 2026

Sheraton Hartford Hotel at Bradley Airport
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
$80 nightly
The price is $92 total per night from Feb 2 to Feb 3
$92 total
Feb 2 - Feb 3
Total with taxes and fees
7.8/10 Good! (999 reviews)
Great place.

Reviewed on Jan 2, 2026

Extended Stay America Suites Hartford Farmington
The Farmington Inn & Suites

The Farmington Inn & Suites

3 out of 5
827 Farmington Ave Farmington CT
Fully refundableReserve now, pay when you stay
$105 nightly
The price is $121 total per night from Jan 11 to Jan 12
$121 total
Jan 11 - Jan 12
Total with taxes and fees
8.8/10 Excellent! (1,000 reviews)
Always cozy with lovely staff. The pet-friendly rooms are great. Love the breakfast and the afternoon cookies/tea!

Reviewed on Jan 2, 2026

The Farmington Inn & Suites
See all 812 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

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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 $160 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.