Deals on vacations and trips to Windsor

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Windsor flight + hotel vacation packages

Price found within the past 48 hours. Click for updated prices.
The Best Way Inn

The Best Way Inn

2 out of 5
West New Haven
Price was $297, price is now $234 per person
$234
per person
Mar 4 - Mar 9
found 14 hours ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
Staff at the 24-hour front desk can provide around-the-clock assistance. Take advantage of the free self parking.
Comfort Inn Naugatuck-Shelton, CT

Comfort Inn Naugatuck-Shelton, CT

2.5 out of 5
Save 100% on your flight
Price was $439, price is now $334 per person
$334
per person
Mar 4 - Mar 9
found 14 hours ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
This hotel doesn't skimp on freebies - guests receive free buffet breakfast, free WiFi, and free self parking. Traveling on business? Take advantage of the 24-hour business center and free internet in public areas. Dry cleaning, luggage storage, and laundry facilities are also on offer.
Motel 6 New Haven - Branford, CT

Motel 6 New Haven - Branford, CT

2 out of 5
Price was $301, price is now $240 per person
$240
per person
Mar 4 - Mar 9
found 14 hours ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
A restaurant, free self parking, and a 24-hour front desk are among this motel's amenities. WiFi in public areas is free. A snack bar/deli is also provided.
Whitney Inn & Suites

Whitney Inn & Suites

2 out of 5
Price was $378, price is now $307 per person
$307
per person
Mar 4 - Mar 9
found 14 hours ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
This hotel doesn't skimp on freebies - guests receive free WiFi and free self parking. Express check-in, express check-out, and luggage storage are also on offer.
Cheshire Welcome Inn

Cheshire Welcome Inn

2.5 out of 5
Price was $406, price is now $333 per person
$333
per person
Mar 4 - Mar 9
found 14 hours ago
Roundtrip flight included
Orlando (MCO) to New Haven (HVN)
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. The front desk is staffed around-the-clock and laundry facilities are on offer.

Top Windsor hotels deals

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
$115 nightly
The price is $132 total per night
$132 total
Feb 15 - Feb 16
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.
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
$113 nightly
The price is $130 total per night
$130 total
Jan 22 - Jan 23
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.
Pool
Breakfast included
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
$132 nightly
The price is $152 total per night
$152 total
Feb 16 - Feb 17
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.
Pool
Breakfast included
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
$139 nightly
The price is $160 total per night
$160 total
Jan 30 - Jan 31
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.
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
$122 nightly
The price is $141 total per night
$141 total
Jan 25 - Jan 26
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.
Free airport shuttle
Pet friendly
The Capitol Hotel

The Capitol Hotel

3 out of 5
440 Asylum St Hartford CT
Free Cancellation
Reserve now, pay when you stay
$88 nightly
The price is $102 total per night
$102 total
Jan 19 - Jan 20
Total with taxes and fees
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
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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

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

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

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

Frequently asked questions

How much are vacation packages to Windsor?
Travelocity has flight and hotel packages from as low as $234. 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