Windsor Vacation Packages

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Flight and hotel packages to Windsor

Price found within the past 48 hours. Click for updated prices.
Motel 6 Niantic, CT - New London

Motel 6 Niantic, CT - New London

2 out of 5
per person
Jul 26 - Jul 28
Roundtrip non-stop flight included
Indianapolis (IND) to New Haven (HVN)
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. A snack bar/deli and laundry facilities are also provided.
Hilton Garden Inn Hartford North/Bradley Int'l Airport

Hilton Garden Inn Hartford North/Bradley Int'l Airport

3 out of 5
per person
Jul 12 - Jul 15
Roundtrip non-stop flight included
Tampa (TPA) to New Haven (HVN)
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.
Residence Inn by Marriott Hartford/Windsor

Residence Inn by Marriott Hartford/Windsor

3 out of 5
per person
Jul 12 - Jul 15
Roundtrip non-stop flight included
Tampa (TPA) to New Haven (HVN)
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. Guests will appreciate freebies like buffet breakfast and parking.
The Niantic Inn

The Niantic Inn

2 out of 5
per person
Jul 26 - Jul 28
Roundtrip non-stop flight included
Indianapolis (IND) to New Haven (HVN)
This hotel features free WiFi in public areas, laundry facilities, and free self parking. Enjoy the free on-the-go breakfast each morning. A garden, a picnic area, and express check-in are also on offer.
Aderi Hotel Niantic

Aderi Hotel Niantic

2 out of 5
per person
Jul 26 - Jul 28
Roundtrip non-stop flight included
Indianapolis (IND) to New Haven (HVN)
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Traveling on business? Take advantage of the express check-in and free internet in public areas. There's a gym on site, and a 24-hour front desk and a garden are also provided.

Top Windsor hotel deals

HYATT house Hartford North/Windsor

HYATT house Hartford North/Windsor

3 out of 5
200 Corporate Dr, Windsor, CT
Free Cancellation
The price is $118 per night
$118
per night
May 29 - May 30
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.
Pet friendly
Breakfast included
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
The price is $127 per night
$127
per night
Jun 2 - Jun 3
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.
Pet friendly
Breakfast available
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
The price is $179 per night
$179
per night
May 31 - Jun 1
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.
Pet friendly
Breakfast available
Courtyard By Marriott Hartford/Windsor Airport

Courtyard By Marriott Hartford/Windsor Airport

3 out of 5
1 Day Hill Rd, Windsor, CT
Free Cancellation
Reserve now, pay when you stay
The price is $161 per night
$161
per night
Jun 14 - Jun 15
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. Free self parking, a coffee shop, and a terrace are also offered.
Breakfast available
Parking included
Holiday Inn Express Southington, an IHG Hotel

Holiday Inn Express Southington, an IHG Hotel

2.5 out of 5
120 Laning St, Southington, CT
Free Cancellation
The price is $133 per night
$133
per night
May 23 - May 24
This hotel features a 24-hour gym and a seasonal outdoor pool. 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.
MGM Springfield

MGM Springfield

4 out of 5
One MGM Way, Springfield, MA
The price is $129 per night
$129
per night
May 20 - May 21
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.
Pet friendly
Breakfast available
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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 in Windsor

Image for Northwest Park

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
Image for Windsor Historical Society

Windsor Historical Society

5/5(4 reviews)

You can spend an afternoon browsing the exhibits at Windsor Historical Society during your trip to Windsor. Experience the great live music or attend a sporting event in this family-friendly area.

Windsor Historical Society
Image for SS&C SummerWind Performing Arts Center

SS&C SummerWind Performing Arts Center

Enjoy a show at SS&C SummerWind Performing Arts Center, a storied theater in Windsor. Experience the area's acclaimed theater scene or attend a sporting event.

SS&C SummerWind Performing Arts Center

Photos of local treasures

Frequently asked questions

How much are vacation packages to Windsor?
You’ll be pleasantly surprised — you can unwind in Windsor for as low as $397. Allow Travelocity to save you time and stress with our awesome vacation package deals. With hotels, flights and tours all ready to go, what are you waiting for?
How long should my Windsor vacation be?
Most people lock in their hotel for 2 nights in Windsor. But that doesn’t necessarily mean you have to. How long you decide to stay depends on how much you want to do on your vacation. If you’d love to see every nook and cranny of this awesome location, consider staying another night or so (or even longer!).
Where can I get the best vacation package deals for Windsor?
Travelocity is here to help you snag an unbeatable Windsor package deal. With more than 400 partner airlines and 1,000,000 properties across the globe, you’re bound to be able to put together the perfect itinerary.
Why should I purchase my Windsor vacation package via Travelocity?
We’ve got experiences to suit every kind of globetrotter, top-notch service and support available 24/7. And the icing on the cake is we’ll match any cheaper price you come across with our Price Match Guarantee.
Can I save money on my Windsor car rental if I combine it with hotels and flights?
Bundling your hotel, car and flight into a Windsor vacation package is an excellent way to score the best deal. Plus, having your own car rental gives you absolute freedom to find your way to all those big sights you’re hoping to explore. Located 100 mi from Windsor, Times Square is one place that should be on your to-do list. Fill up the tank and make a day trip of it.
What is the best time of year to go to Windsor?
If budget is what’s driving your itinerary, you’ll score the best prices in . is usually the dearest time of year. Most travelers come here during March, May and August. If you’d prefer to avoid peak season, visit during December, January and February.
Which airport is best for Windsor?
Bradley Intl. Airport (BDL) is 6 mi from the city center and is the beginning point for many exciting adventures. Alternatively, Tweed - New Haven Regional Airport (HVN) is 40 mi away from central Windsor and Hartford, CT (HFD-Hartford - Brainard) is 8 mi away from central Windsor.
What is there to do in Windsor?
While veering off the tourist trail can be rewarding, you shouldn’t miss the big sights that make a destination famous. SS&C SummerWind Performing Arts Center and Windsor Arts Center are a couple of them in Windsor.
Where should I stay when visiting Windsor?
Many people choose to check in to the Hilton Garden Inn Hartford North/Bradley Intl Airport. It’s a great base for your Windsor escape.