Winsted Vacation Packages 2026 from $776

Winsted flight + hotel vacation packages

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

New Haven Hotel

Downtown New Haven

$776

per person

Dec 17 - Dec 23

found 13 hours ago

Roundtrip flight included

Orlando (MCO) 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.

Head of Pond House

Save 100% on your flight

$897

per person

Dec 2 - Dec 7

found 15 hours ago

Roundtrip flight included

Atlanta (ATL) to New Haven (HVN)

A seasonal outdoor pool is featured at this bed & breakfast, along with free self parking. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A terrace, a garden, and a communal living room are also on offer.

Landing Apartments New Haven Near Dixwell

Newhallville

$931

per person

Dec 17 - Dec 23

found 13 hours ago

Roundtrip flight included

Orlando (MCO) to New Haven (HVN)

This apartment includes free WiFi in public areas and a virtual front desk.

Landing Furnished Apartment Near Yale University

Downtown New Haven

$810

per person

Dec 17 - Dec 23

found 13 hours ago

Roundtrip flight included

Orlando (MCO) to New Haven (HVN)

A gym is featured at this apartment, along with free WiFi in public areas and laundry facilities. A virtual front desk are provided for your convenience.

Hyatus Luxury Residences City Crossing

The Hill

$1,037

per person

Dec 17 - Dec 23

found 13 hours ago

Roundtrip flight included

Orlando (MCO) to New Haven (HVN)

This aparthotel features a 24-hour gym and a seasonal outdoor pool. Traveling for business? Take advantage of the free WiFi in public areas, laundry service, and conference center. Enjoy the a rooftop terrace and perks like free self parking and a free area shuttle.

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 29 - Sep 30

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

Free Cancellation

$101 nightly

$113 total

Oct 19 - Oct 20

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

$169 nightly

$194 total

Oct 1 - Oct 2

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.

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.

Spa

Pet friendly

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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 $776. 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.