Book Exclusive Winsted Vacation Packages

Choose one or more items to build your trip:

Winsted flight + hotel packages

Price found within the past 48 hours. Click for updated prices.
Water's Edge Resort & Spa

Water's Edge Resort & Spa

3.5 out of 5
Westbrook Center
Price was CA $1,097, price is now CA $1,033 per person
CA $1,033
per person
Sep 14 - Sep 17
found 1 day ago
Roundtrip flight included
Ottawa (YOW) to New Haven (HVN)
Book a stay at this beach resort in Westbrook. Enjoy free WiFi, free parking, and an outdoor pool. Our guests praise the helpful staff in our reviews. Popular attractions Tanger Outlets and Westbrook Town Beach are located nearby.
Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!

5 out of 5
North End
Price was CA $1,508, price is now CA $1,310 per person
CA $1,310
per person
Aug 28 - Aug 30
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to New Haven (HVN)
Book a stay at this luxury vacation home in Bridgeport. Enjoy free WiFi, free parking, and a garden. Popular attractions Hartford HealthCare Amphitheater and Svihra Park are located nearby.
Head of Pond House

Head of Pond House

3 out of 5
Price was CA $1,504, price is now CA $1,336 per person
CA $1,336
per person
Sep 14 - Sep 17
found 1 day ago
Roundtrip flight included
Ottawa (YOW) to New Haven (HVN)
Book a stay at this business-friendly B&B in Water Mill. Enjoy free breakfast, free WiFi, and free parking. Popular attractions The Hamptons Beaches and Shinnecock Hills Golf Course are located nearby.
Quality Suites Stratford

Quality Suites Stratford

2.5 out of 5
Price was CA $1,298, price is now CA $1,237 per person
CA $1,237
per person
Aug 29 - Sep 5
found 10 hours ago
Roundtrip non-stop flight included
Calgary (YYC) to New Haven (HVN)
Book a stay at this golf hotel in Stratford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Hartford HealthCare Amphitheater and Perry House are located nearby.
Saybrook Point Resort & Marina

Saybrook Point Resort & Marina

3.5 out of 5
Old Saybrook Center
Price was CA $1,390, price is now CA $1,386 per person
CA $1,386
per person
Sep 14 - Sep 17
found 1 day ago
Roundtrip flight included
Ottawa (YOW) to New Haven (HVN)
Book a stay at this spa hotel in Old Saybrook. Enjoy free WiFi, free parking, and 2 outdoor pools. Our guests praise the restaurant and the helpful staff in our reviews. Popular attractions Fort Saybrook Monument Park and General William Hart House are located nearby.

Top Winsted hotels deals

Family-Friendly Highland Lake Waterfront w/ Private Dock & Shallow Walk-In — 5BR

Family-Friendly Highland Lake Waterfront w/ Private Dock & Shallow Walk-In — 5BR

Winchester CT
Get rates
Stay at this vacation home in Winsted. Enjoy free WiFi, a fitness center, and a garden. Popular attractions The Marina at Highland Lake and Winchester Historical Society are located nearby.
Kitchen
Washer
The Farmington Inn & Suites

The Farmington Inn & Suites

3 out of 5
827 Farmington Ave Farmington CT
Free cancellation
Reserve now, pay when you stay
The price is CA $238 per night
CA $238
CA $298 total
Aug 2 - Aug 3
includes taxes & fees
Book a stay at this business-friendly hotel in Farmington. Enjoy free breakfast, room service, and a health club. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Miss Porter's School and Hill-Stead Museum are located nearby.
Breakfast included
Pet-friendly
Sheraton Hartford Hotel at Bradley Airport

Sheraton Hartford Hotel at Bradley Airport

3.5 out of 5
1 Bradley International Airport Windsor Locks CT
Free cancellation
Reserve now, pay when you stay
The price is CA $335 per night
CA $335
CA $385 total
Aug 15 - Aug 16
includes taxes & fees
Book a stay at this business-friendly hotel in Windsor Locks. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the clean rooms in our reviews. Popular attractions Connecticut Fallen Firefighters Memorial and New England Air Museum are located nearby.
Pet-friendly
Free WiFi
Avon Old Farms Hotel

Avon Old Farms Hotel

3.5 out of 5
279 Avon Mountain Rd Avon CT
Free cancellation
Reserve now, pay when you stay
The price is CA $272 per night
CA $272
CA $343 total
Aug 12 - Aug 13
includes taxes & fees
Book a stay at this family-friendly hotel in Avon. Enjoy free breakfast, free WiFi, and an outdoor pool. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Farmington River and Talcott Mountain Science Center are located nearby.
Pool
Breakfast included
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
Free cancellation
The price is CA $177 per night
CA $177
CA $203 total
Aug 23 - Aug 24
includes taxes & fees
Book a stay at this business-friendly hotel in Windsor Locks. Enjoy free breakfast, free WiFi, and a free airport shuttle. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Connecticut Fallen Firefighters Memorial and New England Air Museum are located nearby.
Pool
Breakfast included
Quality Inn Great Barrington

Quality Inn Great Barrington

2.5 out of 5
372 Main Street Great Barrington MA
Free cancellation
The price is CA $167 per night
CA $167
CA $186 total
Aug 17 - Aug 18
includes taxes & fees
Book a stay at this business-friendly hotel in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. Popular attractions Mahaiwe Performing Arts Center and Housatonic River Walk are located nearby.
Breakfast included
Parking included
Don't see what you're looking for?
See all available properties in Winsted
View all properties
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.

Stay near popular Winsted attractions

Highland Lake

Commune with nature and explore the great outdoors at Highland Lake during your travels in Winchester.
See properties

Winsted Vacations

If you're staying in Winsted and you don't know a lot about it, don't stress — we'll let you in on the basics!

You'll discover this Torrington neighborhood 6 miles (10 kilometers) north of the downtown action.

Visitors to Torrington will be rubbing shoulders with approximately 36,000 residents.

Places to visit in Winsted

Get out into the wider Torrington area and get close to nature with some activities like snowboarding. If you'd really like to head home with some lasting vacation memories, put skiing on your itinerary as well.

Where do you fly into for Winsted?

Put your seat upright, switch off the in-flight film, and prepare for landing at Bradley International Airport (BDL). Want to know the best part? You'll be only 20 miles (32 kilometers) to the east of Winsted.

Frequently asked questions

How much are vacation packages to Winsted?
Travelocity offers great package deals to Winsted, including flights and hotels, starting from as low as CA $1,033. With all the extra money, you could include some awesome tours or perhaps even add a few extra nights to your adventure.
Where can I get the best vacation package deals for Winsted?
Whatever your travel style, Travelocity can help you lock in a great Winsted package deal. All you have to do is mix and match from our 400 airlines and 1,000,000 properties around the world.
Why should I purchase my Winsted vacation bundle with Travelocity?
The three S's — savings, support and a stress-free booking — are just the beginning. Collect lifelong memories and enjoy a fulfilling travel experience knowing you have access to our team of customer support experts around-the-clock. With the Travelocity Price Match Guarantee, you can relax knowing you'll always get the best deal available.
Can I save on my Winsted car rental if I combine it with hotels and flights?
Booking a Winsted vacation package with Travelocity is one of the best ways to save cold, hard cash. Bundle a car, hotel and flight, or any combination of them, and get access to great discounts. You could also throw in experiences and activities. After you've picked up the keys to the rental car, head out of the neighborhood and find out what the surrounding area has to offer. Around 153 kilometers from Winsted, Times Square is worth a road trip.
What is there to do in Winsted?
Highland Lake and Laurel Lanes are popular with so many visitors. Cross these sights off your must-see list and discover what the hype is about.

Photos of local treasures

Browse Winsted vacation photos for more inspiration

A tranquil lake with a stone tower, surrounded by autumn-colored trees and a clear sky.
A brick building with green shutters, a white door, and a brick entrance.
A tractor with large tires and a red frame, parked next to a birch tree in a forested area with autumn-colored foliage.