Deals on vacations and trips to Windsor

Save when you book Windsor package deals

Choose two or more items and save on your trip:

Windsor flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
Holiday Inn Cheshire - Southington by IHG

Holiday Inn Cheshire - Southington by IHG

3 out of 5
per person
Sep 22 - Sep 25
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
This hotel features an indoor pool, a hot tub, and a restaurant. Traveling on business? Take advantage of the 24-hour business center and free WiFi in public areas. Enjoy the gym and perks like free self parking.
Graduate by Hilton New Haven

Graduate by Hilton New Haven

4 out of 5
Downtown New Haven
per person
Sep 22 - Sep 25
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
A restaurant and a bar/lounge are featured at this hotel. WiFi in public areas is free. A coffee shop and luggage storage are also provided.
Omni New Haven Hotel at Yale

Omni New Haven Hotel at Yale

4 out of 5
Downtown New Haven
per person
Sep 22 - Sep 25
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.
Holiday Inn Express Southington by IHG

Holiday Inn Express Southington by IHG

2.5 out of 5
per person
Sep 22 - Sep 25
found 1 day ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
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.

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
$144 nightly
The price is $165 total per night
$165 total
Aug 29 - Aug 30
Total includes 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.
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
$127 nightly
The price is $146 total per night
$146 total
Sep 1 - Sep 2
Total includes 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.
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
$144 nightly
The price is $166 total per night
$166 total
Aug 31 - Sep 1
Total includes 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.
Pool
Breakfast included
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
$152 nightly
The price is $175 total per night
$175 total
Aug 31 - Sep 1
Total includes 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. Free self parking, a coffee shop, and a terrace are also offered.
Parking included
Free WiFi
Hampton Inn Hartford/Airport

Hampton Inn Hartford/Airport

2.5 out of 5
2168 Poquonock Ave, Windsor, CT
Free Cancellation
Reserve now, pay when you stay
$152 nightly
The price is $175 total per night
$175 total
Aug 24 - Aug 25
Total includes 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.
Pool
Breakfast included
Residence Inn by Marriott Hartford/Windsor

Residence Inn by Marriott Hartford/Windsor

3 out of 5
100 Dunfey Ln, Windsor, CT
Free Cancellation
Reserve now, pay when you stay
$142 nightly
The price is $163 total per night
$163 total
Aug 21 - Aug 22
Total includes 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.
Pool
Breakfast included
Don't see what you're looking for?
See all available properties in Windsor
View all properties
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

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

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.

Loomis Chaffee School

Windsor Arts Center

Rich with history, Windsor Arts Center is a cultural attraction worth visiting in Windsor. Experience the area's acclaimed theater scene 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 $265. 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

Browse Windsor vacation photos for more inspiration