Windsor Vacation Packages 2026 from $423

Windsor flight + hotel vacation packages

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

Pier Blue Inn Old Saybrook - Essex

Saybrook Manor

$423

per person

Jun 19 - Jun 21

found 1 day ago

Roundtrip flight included

Fort Myers (RSW) to New Haven (HVN)

This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. If you want to take your pet along, this pet-friendly property offers everything you'll need for your pet including an off-leash area. A picnic area and barbecue grills are also provided.

Beechmont - Perfect for Family Retreat!

North End

Save 100% on your flight

$2,540

per person

Jul 1 - Jul 8

found 1 day ago

Roundtrip flight included

Miami (MIA) 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.

Omni New Haven Hotel at Yale

Downtown New Haven

Save 100% on your flight

$810

per person

Jul 6 - Jul 13

found 2 hours ago

Roundtrip flight included

Fort Lauderdale (FLL) to New Haven (HVN)

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the business center, free WiFi in public areas, and valet parking. Self parking, a coffee shop, and limo/town car service are also offered.

Madison Beach Hotel

Madison Center

Save 100% on your flight

$1,048

per person

Jun 19 - Jun 21

found 1 day ago

Roundtrip flight included

Fort Myers (RSW) to New Haven (HVN)

This smoke-free hotel features a private beach, a full-service spa, and a restaurant. Enjoy beachfront dining and relax with sun loungers and beach umbrellas. Enjoy the gym and perks like free WiFi.

Landing Furnished Apartment Near Yale University

Downtown New Haven

$756

per person

Jul 6 - Jul 13

found 2 hours ago

Roundtrip flight included

Fort Lauderdale (FLL) 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.

Top Windsor hotels deals

HYATT house Hartford North/Windsor

200 Corporate Dr Windsor CT

Free Cancellation

Reserve now, pay when you stay

$144 nightly

$166 total

Apr 23 - Apr 24

Total with taxes and fees

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the gym and free perks like buffet breakfast and free self parking.

Residence Inn by Marriott Hartford/Windsor

100 Dunfey Ln Windsor CT

Free Cancellation

Reserve now, pay when you stay

$132 nightly

$152 total

May 3 - May 4

Total with taxes and fees

This hotel features a gym and a seasonal outdoor pool. Traveling on business? Take advantage of the business center and free WiFi in public areas. Enjoy the free buffet breakfast each morning.

Marriott Hartford/Windsor Airport

28 Day Hill Rd Windsor CT

Free Cancellation

Reserve now, pay when you stay

$189 nightly

$217 total

Apr 24 - Apr 25

Total with taxes and fees

This hotel features a restaurant, an indoor pool, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Enjoy the gym and perks like free self parking.

Hilton Garden Inn Hartford North/Bradley Int'l Airport

555 Corporate Dr Windsor CT

Free Cancellation

Reserve now, pay when you stay

$133 nightly

$152 total

May 10 - May 11

Total with taxes and fees

This hotel features a restaurant, a 24-hour gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Enjoy free perks like free self parking and an area shuttle.

Courtyard By Marriott Hartford/Windsor Airport

1 Day Hill Rd Windsor CT

Free Cancellation

Reserve now, pay when you stay

$127 nightly

$146 total

Apr 23 - Apr 24

Total with taxes and fees

This hotel features a restaurant, a gym, and a bar/lounge. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Self parking, a coffee shop, and a terrace are also offered.

Hampton Inn Hartford/Airport

2168 Poquonock Ave Windsor CT

Free Cancellation

Reserve now, pay when you stay

$133 nightly

$153 total

Apr 26 - Apr 27

Total with taxes and fees

This hotel features an indoor pool and a 24-hour gym. Traveling on business? Take advantage of the 24-hour business center, free WiFi in public areas, and free airport shuttle. Guests will appreciate freebies like buffet breakfast and free self parking.

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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.

Popular places to visit

Northwest Park

4.5/5(4 reviews)

Explore the great outdoors at Northwest Park, a lovely green space in Windsor. Experience the area's great live music or attend a sporting event.

Loomis Chaffee School

Enjoy the collegiate vibe at Loomis Chaffee School as part of your travels around Windsor. While in this family-friendly area, you can savor the top-notch restaurants.

Oliver Ellsworth Homestead

5/5(4 reviews)

Find out about the history of Windsor with a stop at Oliver Ellsworth Homestead. Experience the area's acclaimed theater scene and great live music.

Frequently asked questions

How much are vacation packages to Windsor?

Travelocity has flight and hotel packages from as low as $423. With these kinds of savings, you'll be exploring all of Windsor in the blink of an eye.

How long should my Windsor vacation be?

Most sightseers vacation in Windsor for approximately 2 nights. But traveling is all about finding new adventures and making memories — why not book a couple of more nights so you can do just that?

Where can I get the best vacation package deals for Windsor?

Travelocity can help you get a great Windsor package deal. With no less than 400 airlines and 1,000,000 properties across the globe, we know you'll find one that works for you.

Why should I book my Windsor vacation package via Travelocity?

From our 24/7 customer support to our range of enticing destinations, we're dedicated to giving you the most unforgettable escape. All you need to do is click and book — our Price Match Guarantee will ensure you get the cheapest price.

Can I save money on my Windsor car rental if I combine it with my hotel or flight?

You certainly can — combine your car, hotel and flight into a Windsor vacation package and you can save a ton. With so much to discover in Windsor, having your own set of wheels will make exploring a breeze. Once you've buckled yourself in, put the stereo on and head toward Times Square, a famous attraction around 100 mi from Windsor.

Which airport is best for Windsor?

There's a very good chance you'll be arriving at Bradley Intl. Airport (BDL), which is 6 mi north of inner Windsor. Tweed - New Haven Regional Airport (HVN) (40 mi away from central Windsor) and Hartford, CT (HFD-Hartford - Brainard) (8 mi away from central Windsor) are your other options.

What is there to do in Windsor?

Windsor is full of places to discover, including Oliver Ellsworth Homestead and Windsor Meadows State Park. These well-known attractions are on most tourists' must-see lists.

Where should I stay when visiting Windsor?

If you're after a place to spend your nights, take a look at the Hilton Garden Inn Hartford North/Bradley Intl Airport. It's the top choice for many travelers.