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Windsor flight + hotel vacation packages

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Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

4 out of 5
Downtown New Haven
Save 100% on your flight
per person
Aug 7 - Aug 11
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
This smoke-free hotel features 2 restaurants, a bar/lounge, and a 24-hour gym. 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.
Luxury Apartments by Hyatus at Pierpont

Luxury Apartments by Hyatus at Pierpont

4 out of 5
The Hill
Save 100% on your flight
per person
Aug 7 - Aug 11
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
This aparthotel features a 24-hour gym and a seasonal outdoor pool. Enjoy the a rooftop terrace and perks like free self parking and a free area shuttle. Free WiFi in public areas, a garden, and a lobby fireplace are also on offer.
Microtel Inn & Suites by Wyndham Uncasville Casino Area

Microtel Inn & Suites by Wyndham Uncasville Casino Area

2.5 out of 5
per person
Aug 14 - Aug 20
found 1 day ago
Roundtrip non-stop flight included
Dallas (DFW) to New Haven (HVN)
This hotel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Traveling for business? Take advantage of the 24-hour business center, express check-out, and conference space. The front desk is staffed around-the-clock and laundry facilities are on offer.
Hampton Inn & Suites Hartford/East Hartford

Hampton Inn & Suites Hartford/East Hartford

2.5 out of 5
per person
Aug 7 - Aug 12
found 6 hours ago
Roundtrip non-stop flight included
Orlando (MCO) to New Haven (HVN)
This hotel features an indoor pool and a 24-hour gym. There's no skimping on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. A 24-hour business center, a lobby fireplace, and express check-in are also on offer.
Home2 Suites by Hilton East Haven New Haven

Home2 Suites by Hilton East Haven New Haven

3 out of 5
The Centre
Save 100% on your flight
per person
Aug 7 - Aug 11
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
This inn features an indoor pool and a gym. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Guests will appreciate freebies like buffet breakfast and free self parking.

Top Windsor hotels deals

Marriott Hartford/Windsor Airport

Marriott Hartford/Windsor Airport

3.5 out of 5
28 Day Hill Rd, Windsor, CT
Free Cancellation
Reserve now, pay when you stay
Get rates
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.
Pool
Free airport shuttle
Hilton Garden Inn Hartford North/Bradley Int'l Airport

Hilton Garden Inn Hartford North/Bradley Int'l Airport

3 out of 5
555 Corporate Dr, Windsor, CT
Free Cancellation
Reserve now, pay when you stay
Get rates
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.
Free airport shuttle
Pet friendly
HYATT house Hartford North/Windsor

HYATT house Hartford North/Windsor

3 out of 5
200 Corporate Dr, Windsor, CT
Free Cancellation
Reserve now, pay when you stay
Get rates
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.
Pool
Breakfast included
The Capitol Hotel

The Capitol Hotel

3 out of 5
440 Asylum St, Hartford, CT
Free Cancellation
Reserve now, pay when you stay
Get rates
This hotel doesn't skimp on freebies - guests receive free full breakfast and free WiFi. Traveling on business? Take advantage of the 2 conference rooms, business center, and express check-out. Enjoy the 24-hour gym and conveniences like a 24-hour front desk and laundry facilities.
Breakfast included
Pet friendly
MGM Springfield

MGM Springfield

4 out of 5
One MGM Way, Springfield, MA
Get rates
This hotel features a casino and 8 restaurants. Relax with a drink at one of the 5 bars/lounges and enjoy perks like free self parking. There's a seasonal outdoor pool on site, and a 24-hour front desk and a coffee shop are also provided.
Pool
Pet friendly
Baymont by Wyndham East Windsor Bradley Airport

Baymont by Wyndham East Windsor Bradley Airport

2.5 out of 5
260 Main St, East Windsor, CT
Free Cancellation
Reserve now, pay when you stay
Get rates
This hotel doesn't skimp on freebies - guests receive free on-the-go breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the 2 conference rooms, along with the business center. Enjoy the gym and conveniences like a 24-hour front desk and free newspapers.
Breakfast included
Pet friendly
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See all available properties in Windsor
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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.

Northwest Park

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.

Oliver Ellsworth Homestead

Windsor Arts Center

5/5(2 reviews)

Rich with history, Windsor Arts Center is a cultural attraction worth visiting in Windsor. Experience the area's great live music or attend a sporting event.

Windsor Arts Center

Frequently asked questions

How much are vacation packages to Windsor?
Travelocity has flight and hotel packages from as low as $462. 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.

Photos of local treasures

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