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.
Microtel Inn & Suites by Wyndham Uncasville Casino Area

Microtel Inn & Suites by Wyndham Uncasville Casino Area

2.5 out of 5
per person
Oct 13 - Oct 16
found 11 hours ago
Roundtrip flight included
Toronto (YYZ) to New Haven (HVN)
8.8/10 Excellent! (1,703 reviews)
It's a decent place to stay, not far from the casino.

Reviewed on Jul. 24, 2025

Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

4 out of 5
Downtown New Haven
per person
Oct 13 - Oct 16
found 11 hours ago
Roundtrip flight included
Toronto (YYZ) to New Haven (HVN)
8.4/10 Very Good! (1,015 reviews)
I love the hotel and the service. Top Notch.

Reviewed on Jul. 24, 2025

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 13 - Oct 16
found 11 hours ago
Roundtrip flight included
Toronto (YYZ) to New Haven (HVN)
8.8/10 Excellent! (1,002 reviews)
I had made reservation after midnight while tired on the road, needing a place to sleep, the night manager fixed my reservation so I could get a room immediately. Super helpful and much appreciated.

Reviewed on Jul. 23, 2025

Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

3.5 out of 5
Old Saybrook Center
per person
Oct 13 - Oct 16
found 11 hours ago
Roundtrip flight included
Toronto (YYZ) to New Haven (HVN)
9.4/10 Exceptional! (1,003 reviews)
Rooms were large and spacious but quite dark. The Choo Choo lounge and the outside bar were very pleasant. The onsite dining restaurant was disappointing, food was below expectations and did not live up to their rating. Staff were all very pleasant. Parking was a difficult but it is high season.

Reviewed on Jul. 21, 2025

Graduate by Hilton New Haven

Graduate by Hilton New Haven

4 out of 5
Downtown New Haven
per person
Oct 13 - Oct 16
found 11 hours ago
Roundtrip flight included
Toronto (YYZ) to New Haven (HVN)
9.2/10 Wonderful! (831 reviews)
I love this hotel! I've stayed in several other hotels in NH but this one is my favorite. Love the collegiate decor and the Yale theme throughout. The staff is helpful, the rooms are small but cozy and nicely decorated. The location is ideal and love having a cafe in the lobby to grab coffee in the AM.

Reviewed on Jul. 22, 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 $167 per night from Jul 27 to Jul 28
CA $167
CA $192 total
Jul 27 - Jul 28
includes taxes & fees
8.8/10 Excellent! (1,096 reviews)
Oh baby!!!
"Enjoyed it, solid visit!!"

Reviewed on Jul. 22, 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
The price is CA $174 per night from Aug 3 to Aug 4
CA $174
CA $224 total
Aug 3 - Aug 4
includes taxes & fees
8.6/10 Excellent! (999 reviews)
"The best"

Reviewed on Jul. 19, 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
The price is CA $184 per night from Aug 8 to Aug 9
CA $184
CA $212 total
Aug 8 - Aug 9
includes taxes & fees
8/10 Very Good! (1,004 reviews)
"People made the difference in a very good way."

Reviewed on Jul. 15, 2025

DoubleTree by Hilton Hartford - Bradley Airport
See all 815 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?
Offering great value package deals from CA $450 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.