Winsted Vacation Packages 2026 from $686

Winsted flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.

Heritage Hotel, Golf & Conference Center

$686

per person

Oct 29 - Nov 2

found 21 hours ago

Roundtrip non-stop flight included

Denver (DEN) to New Haven (HVN)

A golf course and an indoor pool are featured at this smoke-free hotel. Enjoy the gym and perks like free self parking and free WiFi. Enjoy the outdoor tennis court and unwind at the bar/lounge and poolside bar.

Beechmont - Perfect for Family Retreat!

North End

$1,407

per person

Nov 25 - Nov 28

found 17 hours ago

Roundtrip flight included

Chicago (ORD) to New Haven (HVN)

This vacation home doesn't skimp on freebies - guests receive free WiFi and free self parking. A terrace, a garden, and a communal living room are also on offer.

Las Flores Villa

$2,566

per person

Nov 27 - Nov 29

found 15 hours ago

Roundtrip flight included

Chicago (ORD) to New Haven (HVN)

This vacation home features an outdoor pool and a hot tub. Families will appreciate the playground and onsite laundry facilities. Enjoy the sauna and perks like free self parking.

Mayflower Inn & Spa, Auberge Collection

$2,761

per person

Nov 27 - Nov 29

found 15 hours ago

Roundtrip flight included

Chicago (ORD) to New Haven (HVN)

A full-service spa, an indoor pool, and a restaurant are all featured at this luxury hotel. Enjoy the gym and perks like free valet parking and free WiFi. You'll appreciate the seasonal outdoor pool, bar/lounge, and laundry facilities.

New Haven Hotel

Downtown New Haven

$720

per person

Oct 29 - Nov 2

found 21 hours ago

Roundtrip non-stop flight included

Denver (DEN) to New Haven (HVN)

A gym, self parking, and laundry facilities are featured at this hotel. WiFi in public areas is free. Traveling on business? Take advantage of the 2 conference rooms, along with dry cleaning/laundry services.

Top Winsted hotels deals

Enjoy a restful stay with fast internet, smart TV and the company of your pet.

winsted CT

$206 nightly

$234 total

Sep 30 - Oct 1

Total with taxes and fees

A hot tub is featured at this apartment, along with a garden.

Waterfront House & Guest House Available in Winchester, CT!

Winchester CT

Get rates

This vacation home features laundry facilities.

Kitchen

Washer

Quality Inn Great Barrington

372 Main Street Great Barrington MA

$101 nightly

$113 total

Oct 20 - Oct 21

Total with taxes and fees

A gym, free self parking, and free newspapers are featured at this hotel. Guests will appreciate free perks like on-the-go breakfast and WiFi in public areas. A picnic area and barbecue grills are also provided.

Breakfast included

Parking included

The Farmington Inn & Suites

827 Farmington Ave Farmington CT

Free Cancellation

Reserve now, pay when you stay

$173 nightly

$199 total

Sep 30 - Oct 1

Total with taxes and fees

This hotel features a restaurant, a gym, and a bar/lounge. Business travelers can take advantage of the 24-hour business center. Enjoy the free continental breakfast each morning.

Breakfast included

Pet friendly

Homewood Suites by Hilton Hartford-Farmington

2 Farm Glen Blvd Farmington CT

Free Cancellation

Reserve now, pay when you stay

$147 nightly

$169 total

Oct 4 - Oct 5

Total with taxes and fees

This hotel features an indoor pool, a gym, and a restaurant. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Free perks include buffet breakfast, free self parking, and an area shuttle.

Pool

Breakfast included

Delamar West Hartford

1 Memorial Road West Hartford CT

Free Cancellation

Reserve now, pay when you stay

$378 nightly

$432 total

Oct 25 - Oct 26

Total with taxes and fees

A full-service spa, a 24-hour gym, and a restaurant are all featured at this smoke-free hotel. Relax with a drink at the bar/lounge and enjoy perks like free valet parking and free WiFi. Free self parking, a 24-hour business center, and a terrace are also offered.

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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.

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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 $686. 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 95 mi 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.