Winsted Holidays

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Your Winsted Holiday

Book a custom holiday package to Winsted and get ready for your next epic adventure. Consider staying in the neighbourhood of Pleasant Valley, which is great for camping and nature, for a real taste of this unique city. If taking in sights is on the agenda during your trip to Winsted, look around major attractions like Highland Lake, Winchester Historical Society and Jerram Winery. Don't put off visiting this destination any longer. Your ultimate Winsted holiday is a couple of clicks away with Expedia.

Winsted Holiday

Winsted Essential Information

Language
English
Currency
U.S dollars
Closest Airport
Bradley Intl. Airport (BDL)
Population
7,700
Max Temp Winter
-1.11ºC
Max Temp Summer
27ºC
Top Sights
Connecticut Valley Winery, Winchester Historical Society and Jerram Winery

Our pick of the best 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 AU$236 per night from 16 July to 17 July
AU$236
16 July - 17 July
includes taxes & fees
8.8/10 Excellent! (1,075 reviews)
less than great
"I have enjoyed this hotel in the past but this time the service was less than ideal and the condition of the hotel was now dirty and unkept, mostly in the lobby and workout room."

Reviewed on 7 Jul. 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 AU$263 per night from 16 July to 17 July
AU$263
16 July - 17 July
includes taxes & fees
8.6/10 Excellent! (1,001 reviews)
"Hotel was clean but the smell throughout wasn’t particularly pleasant."

Reviewed on 8 Jul. 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 AU$251 per night from 27 July to 28 July
AU$251
27 July - 28 July
includes taxes & fees
8/10 Very Good! (1,000 reviews)
"Stay was ok"

Reviewed on 3 Jul. 2025

DoubleTree by Hilton Hartford - Bradley Airport
See all 805 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 Holidays

All Inclusive Holidays

All Inclusive Holidays
Cheap Holidays

Cheap Holidays

Cheap Holidays
beach holidays

Beach Holidays

Beach Holidays

Frequently asked questions

How much does a Winsted holiday package cost?
You can snap up a holiday package to this top destination on Expedia. However, how much your holiday to Winsted costs will depend on the length of stay, season and hotel choice.
What are the cheapest months to go to Winsted?
The off-season is the best time to travel to Winsted if you're on a budget. Another tip for getting cheap Winsted holiday packages? Try to avoid visiting during public holidays and any major events or festivals.
How many days is enough for Winsted?
To get the most out of a Winsted holiday, we recommend staying for 3 days. Divide your time between discovering Winchester Historical Society, Highland Lake and other top attractions, in addition to exploring neighbourhoods like Winchester and West Hill Lake. If you've got some spare time, add a day trip or tour to your Winsted holiday itinerary.
Is it worth booking a holiday package to Winsted?
During your Winsted holiday, you can count on experiencing some top-notch nature and culture. Leave enough time in your itinerary to discover 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 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 holiday package well in advance.
Is it cheaper to book a Winsted holiday as a package?
Expedia holiday 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 personalised Winsted holiday by choosing your favourite airline, accommodation type and car class.
When to book a holiday 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.
How to plan a trip to Winsted?

  1. Choose when to get away: Check your calendar and get your bags packed. Your preferred time of year and the type of activities available will also help you decide when to escape to Winsted.
  2. Set a budget: Consider costs like flights, meals and transportation when working out how much to set aside for your trip to Winsted. Then, select a hotel that works with your budget, whether that's an affordable option or a high-end getaway.
  3. Set the duration of your trip: Start by making a list of all the attractions you'd like to experience in Winsted. Then, estimate how long you'll need at each, including any travel time.
  4. Bundle your flights and hotel: Epic destination, check. Length of stay, check. Now all that's left is to choose a Winsted holiday 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.