Winsted Vacations from $405

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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.
Hilton Garden Inn Hartford North/Bradley Int'l Airport

Hilton Garden Inn Hartford North/Bradley Int'l Airport

3 out of 5
Price was $538, price is now $405 per person
$405
per person
Jan 16 - Jan 19
found 1 day ago
Roundtrip flight included
San Juan (SJU) to New Haven (HVN)
8.8/10 Excellent! (1,018 reviews)
Nice, clean room and friendly staff.

Reviewed on Oct 23, 2025

Madison Beach Hotel

Madison Beach Hotel

4 out of 5
Madison Center
Save 100% on your flight
Price was $1,603, price is now $1,114 per person
$1,114
per person
Nov 23 - Nov 28
found 17 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to New Haven (HVN)
9.4/10 Exceptional! (323 reviews)
Beautiful beach property that gives you such a feeling of luxury all around you. Staff has been great, very clean hallways and entire property. Balcony is beautiful!

Reviewed on Oct 14, 2025

Mayflower Inn & Spa, Auberge Collection

Mayflower Inn & Spa, Auberge Collection

5 out of 5
Save 100% on your flight
Price was $4,404, price is now $3,199 per person
$3,199
per person
Nov 22 - Nov 27
found 16 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to New Haven (HVN)
9.2/10 Wonderful! (53 reviews)
Incredible place - will definitely return.

Reviewed on Aug 19, 2024

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
Price was $1,947, price is now $1,571 per person
$1,571
per person
Dec 15 - Dec 18
found 9 hours ago
Roundtrip flight included
Atlanta (ATL) to New Haven (HVN)
No reviews
Residence Inn by Marriott Southington

Residence Inn by Marriott Southington

3 out of 5
Price was $684, price is now $556 per person
$556
per person
Nov 23 - Nov 28
found 17 hours ago
Roundtrip non-stop flight included
Los Angeles (LAX) to New Haven (HVN)
8.6/10 Excellent! (575 reviews)
Didn't get a chance to enjoy the breakfast or pool as intended, however customer service and cleanliness was outstanding! Plus they gave a small welcome bag with some water and little treats/snacks! Parking was easy, and location even though was by highway, was relatively quiet!

Reviewed on Oct 11, 2025

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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

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
$122 nightly
The price is $141 total per night from Oct 30 to Oct 31
$141 total
Oct 30 - Oct 31
Total with taxes and fees
8/10 Very Good! (1,016 reviews)
The overall property and staff were good. However, I wasn't expecting my double beds to actually be two FULL size beds instead of QUEEN size beds in a Hilton hotel.

Reviewed on Oct 17, 2025

DoubleTree by Hilton Hartford - 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
$101 nightly
The price is $116 total per night from Nov 14 to Nov 15
$116 total
Nov 14 - Nov 15
Total with taxes and fees
7.8/10 Good! (1,019 reviews)
Very reasonably priced with dining options nearby. Staff were very nice. Check-in and checkout were very easy. Unfortunately, I did not know how to adjust the thermostat and made my night uncomfortable.

Reviewed on Oct 16, 2025

Extended Stay America Suites Hartford Farmington
Avon Old Farms Hotel

Avon Old Farms Hotel

3.5 out of 5
279 Avon Mountain Rd, Avon, CT
Fully refundableReserve now, pay when you stay
$149 nightly
The price is $171 total per night from Oct 26 to Oct 27
$171 total
Oct 26 - Oct 27
Total with taxes and fees
8.2/10 Very Good! (1,000 reviews)
The staff was very friendly. The hotel was very warm and inviting. Our room was very clean. The hotel was quiet. The dinner at Seasons was great. The breakfast was good but seating was very limited. My husband and I would definitely go back.

Reviewed on Oct 19, 2025

Avon Old Farms Hotel
See all 806 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 $405 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.