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.
AmeriStay Inn

AmeriStay Inn

2.5 out of 5
Price was $457, price is now $386 per person
$386
per person
Dec 17 - Dec 21
found 1 day ago
Roundtrip non-stop flight included
Portland (PDX) to Kansas City (MCI)
This hotel features free WiFi in public areas, laundry facilities, and free self parking. Enjoy the free continental breakfast each morning. Express check-out, a computer station, and luggage storage are also on offer.
The Elms Hotel & Spa, a Destination by Hyatt Hotel

The Elms Hotel & Spa, a Destination by Hyatt Hotel

4 out of 5
Price was $713, price is now $532 per person
$532
per person
Dec 17 - Dec 21
found 1 day ago
Roundtrip non-stop flight included
Portland (PDX) to Kansas City (MCI)
A full-service spa, 2 hot tubs, and an outdoor pool are all featured at this smoke-free hotel. Traveling on business? Take advantage of the free WiFi in public areas, express check-in, and valet parking. Relax with a drink at one of the 2 bars/lounges and enjoy perks like free self parking.
Stoney Creek Hotel St. Joseph

Stoney Creek Hotel St. Joseph

3.5 out of 5
Price was $562, price is now $468 per person
$468
per person
Dec 17 - Dec 21
found 1 day ago
Roundtrip non-stop flight included
Portland (PDX) to Kansas City (MCI)
This hotel features an outdoor pool and an indoor pool. Traveling on business? Take advantage of the free WiFi in public areas, conference center, and conference space. Enjoy the gym and free perks like buffet breakfast and free self parking.
Ameristar Casino Hotel Kansas City

Ameristar Casino Hotel Kansas City

4 out of 5
Birmingham Bottoms
Price was $651, price is now $551 per person
$551
per person
Dec 20 - Dec 22
found 1 day ago
Roundtrip flight included
Philadelphia (PHL) to Kansas City (MCI)
A casino, 7 restaurants, and a 24-hour gym are all featured at this hotel. There's a bar/lounge on site, and a 24-hour front desk and concierge services are also provided.
Super 8 by Wyndham Mound City

Super 8 by Wyndham Mound City

2.5 out of 5
Price was $503, price is now $429 per person
$429
per person
Dec 17 - Dec 21
found 1 day ago
Roundtrip non-stop flight included
Portland (PDX) to Kansas City (MCI)
Free self parking is available and the hotel's front desk is staffed around-the-clock. Guests will appreciate free perks like continental breakfast and WiFi in public areas. A safe deposit box is also provided.

Top Windsor hotels deals

Windsor Crossroads Motel

Windsor Crossroads Motel

2.5 out of 5
606 North Main Street Windsor MO
Free Cancellation
Reserve now, pay when you stay
$72 nightly
The price is $78 total per night
$78 total
Nov 9 - Nov 10
Total with taxes and fees
This motel doesn't skimp on freebies - guests receive free WiFi and free self parking. A picnic area and barbecue grills are also provided.
Parking included
Free WiFi
Comfort Inn Sedalia Station

Comfort Inn Sedalia Station

2.5 out of 5
3600 W Broadway Blvd Sedalia MO
Free Cancellation
$115 nightly
The price is $131 total per night
$131 total
Oct 31 - Nov 1
Total with taxes and fees
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 dry cleaning are also on offer.
Pool
Breakfast included
Econo Lodge Truman Inn

Econo Lodge Truman Inn

2 out of 5
3501 W Broadway Blvd Sedalia MO
Free Cancellation
Reserve now, pay when you stay
$70 nightly
The price is $80 total per night
$80 total
Oct 26 - Oct 27
Total with taxes and fees
This hotel features an indoor pool and a hot tub. Business travelers can take advantage of the free WiFi in public areas. Enjoy the sauna and free perks like continental breakfast and free self parking.
Pool
Hot Tub
Parkfield Inn

Parkfield Inn

2.5 out of 5
506 Kansas Ave Clinton MO
Free Cancellation
Reserve now, pay when you stay
$117 nightly
The price is $132 total per night
$132 total
Oct 18 - Oct 19
Total with taxes and fees
This hotel features an indoor pool and a hot tub. Traveling on business? Take advantage of the free WiFi in public areas and free internet in public areas. Guests will appreciate freebies like continental breakfast and free self parking.
Pool
Hot Tub
Westbridge Inn and Suites

Westbridge Inn and Suites

2 out of 5
106 S Baird St. Clinton MO
Free Cancellation
Reserve now, pay when you stay
$87 nightly
The price is $98 total per night
$98 total
Nov 16 - Nov 17
Total with taxes and fees
This motel doesn't skimp on freebies - guests receive free continental breakfast, free WiFi, and free self parking. Business travelers can take advantage of the business center. There's an outdoor pool on site, and a 24-hour front desk and a fireplace in the lobby are also provided.
Pool
Breakfast included
Best Western State Fair Inn

Best Western State Fair Inn

3 out of 5
3120 S Limit Sedalia MO
Free Cancellation
Reserve now, pay when you stay
$123 nightly
The price is $140 total per night
$140 total
Oct 25 - Oct 26
Total with taxes and fees
This hotel doesn't skimp on freebies - guests receive free full breakfast, free WiFi, and free self parking. Traveling for business? Take advantage of the business center, express check-in, and conference space. Enjoy the indoor pool and conveniences like a 24-hour front desk and laundry facilities.
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.

Frequently asked questions

How much are vacation packages to Windsor?
Your vacation fantasies can be realized in Windsor from an impressive $386. Our vacation packages include flights and hotels, so organizing your itinerary will be easy as pie. The only thing you'll need to focus on is having a good time.
How long should my Windsor vacation be?
The majority of travelers lock in a hotel for 2 nights in Windsor. But that doesn't mean you have to do that. How long you spend here all depends on what sorts of things you want to do during your vacation. If you want to discover every nook and cranny of this superb place, treat yourself to another couple of nights (or even longer!).
Where can I get the best vacation package deals for Windsor?
You'll come across an excellent range of Windsor package deals on Travelocity. With 400 air carriers and 1,000,000 properties around the globe, putting together your ideal getaway will be easy.
Why should I purchase my Windsor vacation bundle via Travelocity?
With top-notch service, customer support available 24/7 and some of the most gorgeous escapes around, you'll never wander alone. And if you find a better price, we'll match it. That's our Price Match Guarantee.
Will I save money on my Windsor car rental if I combine it with a hotel or flight?
You most certainly can — combine your car, hotel and flight into a Windsor vacation package and you can save a handsome sum. With so much to see and do in Windsor, that rental vehicle will make it easy to explore. Once you've buckled yourself in, crank up the music and cruise toward Worlds of Fun, an unmissable sight around 70 mi from Windsor.
Where should I stay when visiting Windsor?
Many travelers opt to spend their nights at the Windsor Crossroads Motel. It's a great base for your Windsor escape.

Photos of local treasures

Browse Windsor vacation photos for more inspiration