Winsted Vacation Packages

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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.

Top Winsted Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Hartford North/Bradley Int'l Airport

Hilton Garden Inn Hartford North/Bradley Int'l Airport

3 out of 5
per person
Oct 24 - Oct 27
found 11 hours ago
Roundtrip flight included
Toronto (YTO) to New Haven (HVN)
8.8/10 Excellent! (1,009 reviews)
NICE STAFF, GREEN HOTEL, GREAT BAR AND RESTAURANT.

Reviewed on Aug. 1, 2025

Microtel Inn & Suites by Wyndham Uncasville Casino Area

Microtel Inn & Suites by Wyndham Uncasville Casino Area

2.5 out of 5
per person
Oct 24 - Oct 27
found 11 hours ago
Roundtrip flight included
Toronto (YTO) to New Haven (HVN)
8.8/10 Excellent! (1,735 reviews)
Quick , easy fairly clean ( room smelled a little musty ) but wverything else was clean and comfortable

Reviewed on Aug. 5, 2025

Residence Inn by Marriott New Haven Hamden

Residence Inn by Marriott New Haven Hamden

3 out of 5
per person
Sep 8 - Sep 14
found 10 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to New Haven (HVN)
9.4/10 Exceptional! (369 reviews)
It’s always pleasant when I stay here.

Reviewed on Jul. 8, 2025

Graduate by Hilton New Haven

Graduate by Hilton New Haven

4 out of 5
Downtown New Haven
per person
Sep 8 - Sep 14
found 10 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to New Haven (HVN)
9.2/10 Wonderful! (851 reviews)
Great location and was able to park right out front on a Sunday.

Reviewed on Jul. 25, 2025

La Quinta Inn & Suites by Wyndham New Haven

La Quinta Inn & Suites by Wyndham New Haven

3 out of 5
Long Wharf
per person
Sep 8 - Sep 14
found 10 hours ago
Roundtrip non-stop flight included
Edmonton (YEG) to New Haven (HVN)
6/10 (1,057 reviews)
The room was drab but comfortable. The hotel is showing its age and is being refreshed, so the lobby was torn up under construction. The breakfast was the typical cheap minimum.

Reviewed on Aug. 4, 2025

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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
The price is CA $163 per night from Aug 25 to Aug 26
CA $163
CA $187 total
Aug 25 - Aug 26
includes taxes & fees
8.8/10 Excellent! (1,108 reviews)
Basketball HOF
"Because of the rain cable was in and out and telephone didn’t work in the room."

Reviewed on Aug. 3, 2025

Holiday Inn Express & Suites Bradley Airport by IHG
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
The price is CA $186 per night from Aug 15 to Aug 16
CA $186
CA $214 total
Aug 15 - Aug 16
includes taxes & fees
8/10 Very Good! (1,000 reviews)
"Great customer service!"

Reviewed on Aug. 2, 2025

DoubleTree by Hilton Hartford - Bradley Airport
The Farmington Inn & Suites

The Farmington Inn & Suites

3 out of 5
827 Farmington Ave, Farmington, CT
Fully refundableReserve now, pay when you stay
The price is CA $156 per night from Aug 14 to Aug 15
CA $156
CA $204 total
Aug 14 - Aug 15
includes taxes & fees
8.6/10 Excellent! (1,005 reviews)
"The staff was very friendly and helpful. This was a very convenient location for the wedding and reception that we were attending."

Reviewed on Aug. 3, 2025

The Farmington Inn & Suites
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.
All Inclusive Vacations
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Frequently asked questions

How much does a Winsted vacation package cost?
Offering great value package deals from CA $598 on Expedia, you'll be pleasantly surprised at how much a vacation to Winsted costs! Our packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Winsted?
Travel in the off-season and you're likely to score cheap Winsted vacation packages. Bear in mind that public holidays and major festivals and events can impact prices, so do your research before you go.
How many days is enough for Winsted?
We recommend booking a Winsted vacation for at least 3 days. This will give you enough time to visit top sights such as Laurel Lanes and Platt Hill State Park, and check out neighbourhoods like Winchester and West Hill Lake. You could even slot in a day trip outside of Winsted.
Is it worth booking a vacation package to Winsted?
During your Winsted vacation, you can look forward to enjoying some top-notch nature and culture. Leave enough room in your itinerary to explore leading attractions like Highland Lake and Laurel Lanes.
How to find the best Winsted package deals?
Use Expedia's handy filters to help you find some terrific 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 want to save, plan your trip for midweek, or browse for Winsted package deals in the off-peak season. Switch up your travel dates and you may score even better discounts. As a rule of thumb, it's typically best to book your vacation package as soon as possible.
Is it cheaper to book a Winsted vacation as a package?
Expedia vacation packages are designed to help you keep more money in your pocket. Bundle your hotel, car rental and flight into one great-value price and you could save hundreds of dollars. You'll usually land a better deal than booking each component individually. And you'll still have the freedom to create a tailored Winsted vacation by choosing your preferred accommodation type, airline and car class.
When to book a vacation package to Winsted?
If you have your Winsted travel dates finalized, book as soon as you can to grab some terrific deals. With Expedia, you can typically reserve some flights up to a year in advance. Prefer spontaneous getaways? Our last-minute deals are ideal for impromptu escapes.
How to plan a trip to Winsted?

  1. Choose when to go: Check your schedule and get packing. Your favourite time of year and the available activities will also help you decide when to escape to Winsted.
  2. Plan your budget wisely: Besides the price of your accommodations, you should factor in other expenses too. These include food, flights and transportation. Also, set aside a little extra for unexpected costs that could crop up during your trip to Winsted.
  3. Decide your trip length: Think about how much time you want to spend discovering Winsted. Plan your itinerary so you can get to all the attractions and experiences you're interested in at a leisurely pace.
  4. Bundle your hotel and flights: Awesome destination, check. Length of stay, check. All that's left is to find a Winsted vacation package that brings all your bookings together.

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