Windsor Vacation Packages

Book a Hotel + Flight or Car together to unlock savings

  • Plan, book, travel with confidence

  • Better together

    Save up to CA $4,200 when you book a flight and hotel together*

  • Find the right fit

    With over 300,000 hotels worldwide, it's easy to create a perfect package

  • Rest easy

    Plan, book, and manage your trip all in one place

Top Holiday Package Deals in Windsor

Price found within the past 48 hours. Click for updated prices.
Hilton Garden Inn Colorado Springs Airport

Hilton Garden Inn Colorado Springs Airport

3 out of 5
Southeast Colorado Springs
Price was CA $1,587, price is now CA $1,210 per person
CA $1,210
per person
Jul 24 - Jul 31
found 24 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Denver (DEN)
8.8/10 Excellent! (925 reviews)
Sandie was an awesome bartender in the evenings at the bar-grill area. Overall good amenities--average on value when compared to other nearby hotels. Charges for breakfast seemed steep with how much the rooms were, bit staff was friendly and earned their tips. Clean room with no major concerns.

Reviewed on Mar 11, 2026

Patterson Inn

Patterson Inn

3.5 out of 5
Capitol Hill
Price was CA $2,144, price is now CA $1,577 per person
CA $1,577
per person
Jul 1 - Jul 6
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Denver (DEN)
9.6/10 Exceptional! (780 reviews)
Quaint, quirky and quiet.

Reviewed on Apr 23, 2026

DoubleTree by Hilton Colorado Springs

DoubleTree by Hilton Colorado Springs

4 out of 5
Southwest Colorado Springs
Price was CA $1,746, price is now CA $1,307 per person
CA $1,307
per person
Jul 24 - Jul 31
found 24 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Denver (DEN)
8.6/10 Excellent! (1,002 reviews)
My go to. Staff is wonderful and facility very clean.

Reviewed on Apr 9, 2026

Colorado's Best

Colorado's Best

3 out of 5
Northeast Colorado Springs
Price was CA $6,485, price is now CA $4,904 per person
CA $4,904
per person
Jul 24 - Jul 31
found 23 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Denver (DEN)
No reviews
Populus

Populus

4 out of 5
Downtown Denver
Price was CA $2,106, price is now CA $1,603 per person
CA $1,603
per person
Jul 1 - Jul 6
found 1 day ago
Roundtrip non-stop flight included
Edmonton (YEG) to Denver (DEN)
9.4/10 Exceptional! (637 reviews)
Amazing, beautiful room and views. Good vibes. Thoughtful amenities. Fun rooftop bar.

Reviewed on May 7, 2026

Where to stay in Windsor

Find the best Windsor areas and neighborhoods for the activities you enjoy most. Learn more about Windsor
Downtown Denver

Downtown Denver

2 out of top 10 points of interest in this area
4.5/5(103 area reviews)

Dive into this bustling financial and entertainment hub, featuring the 16th Street pedestrian mall, Larimer Square, and the Theatre District. Catch a game at Coors Field or Ball Arena, and explore the neighborhood's vibrant dining scene.

Find hotels in Downtown Denver

Windsor Hotel Deals

Holiday Inn Express Denver Downtown by IHG

Holiday Inn Express Denver Downtown by IHG

3 out of 5
1715 Tremont Place Denver CO
Fully refundable
The price is CA $136 per night from May 24 to May 25
CA $136
CA $158 total
May 24 - May 25
includes taxes & fees
7.2/10 Good! (2,052 reviews)
All of it

Reviewed on May 7, 2026

Holiday Inn Express Denver Downtown by IHG
Hyatt Place Peña Station/Denver Airport

Hyatt Place Peña Station/Denver Airport

3 out of 5
6110 NORTH PANASONIC WAY Denver CO
Fully refundableReserve now, pay when you stay
The price is CA $179 per night from May 24 to May 25
CA $179
CA $209 total
May 24 - May 25
includes taxes & fees
9/10 Wonderful! (2,814 reviews)
Rooms are clean and the staff is all very pleasant we will return.

Reviewed on May 7, 2026

Hyatt Place Peña Station/Denver Airport
Sonesta Denver Downtown

Sonesta Denver Downtown

4 out of 5
1450 Glenarm Place Denver CO
Fully refundableReserve now, pay when you stay
The price is CA $135 per night from May 21 to May 22
CA $135
CA $156 total
May 21 - May 22
includes taxes & fees
8.4/10 Very Good! (2,386 reviews)
Staff are very good indeed.

Reviewed on May 6, 2026

Sonesta Denver Downtown
See all 4,752 properties in Windsor
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.
All Inclusive Vacations
All Inclusive Vacations
Beach Vacations
Beach Vacations
Family Vacations
Family Vacations

Frequently asked questions

How much does a Windsor vacation package cost?
Maybe less than you might think — from as low as CA $1,210, as a matter of fact! By bundling hotels, flights and car rentals into your own custom-made vacation package, your trip to Windsor is just clicks away.
How do I get a cheap travel package to Windsor?
Book everything in one place with our Windsor vacation packages. You'll discover deals on hotels, flights and more that'll keep your pocketbook happy and your adventurousness alive. And, with more than 550 airlines and 1,000,000 hotel options globally to select from, you'll have endless opportunities to mix and match.
Where should I stay in Windsor?
It makes sense to stay near the action. Many travelers like to book hotels around popular attractions, such as Wings Over the Rockies Air and Space Museum, Infinity Stadium and Park and Four Mile House Historic Park.
How far in advance should I book my Windsor vacation?
It can be hard to know exactly when is the ideal time to book your Windsor trip. But usually the earlier you book, the lower the prices. In some cases, you can lock in your flights and hotels up to 12 months prior to departure. If you're eager to escape on a last-minute getaway, no need to fret! There are terrific deals featured on Expedia all the time.
What does an Expedia Windsor travel package include?
Choose from a combination of flights, hotels and rental cars. Once you've made your booking, you can add the fun stuff like experiences and activities. Want to pick your airfare class? That's easily done too. The choice is all yours when it comes to planning your dream Windsor escape.
What should I know before booking a Windsor travel package?
You can save a tidy sum by combining your hotels, airfares and rental cars. Once you've made your booking, you can add on activities or tours. Your next awesome adventure is only a couple of clicks away.
Can I choose my airline with a Windsor Expedia vacation package?
With a vacation package, you're in charge. Whether you're looking to fly to Windsor in business or coach, simply select from the available airline options. Expedia has access to over 550 airline partners globally.
If I'm not able to travel, can I cancel my Windsor vacation package?
Because we understand life can be unpredictable, the answer is yes. To learn more, head to our Customer Service Portal. But generally speaking, if you've booked your Windsor vacation package in the last 24 hours, you may be able to change or cancel it for free. Your hotel, airline or car rental company may impose a fee if you made your booking a while ago.

Discover the most popular places to visit in Windsor

Union Station

Union Station

4.5/5(63 reviews)

You can learn more about the history of Denver when you make a stop at a well-known site like Union Station. Discover the top-notch restaurants and fascinating museums in this vibrant area.

Union Station
Red Rocks Amphitheater

Red Rocks Amphitheater

5/5(34 reviews)

This legendary rock concert venue boasts outstanding acoustics thanks to soaring rock walls that hug the stage.

Red Rocks Amphitheater
Coors Field

Coors Field

4.5/5(24 reviews)

Catch an event at Coors Field during your trip to Denver. Amble around this vibrant area's picturesque gardens or attend a sporting event.

Coors Field

Things to do

Denver CityPASS: Admission to 3, 4, or 5 of Denver's Top Attractions

Denver CityPASS®: Admission to Top 3, 4, or 5 Denver Attractions

CA $74
per adult
98% of travellers recommend
Denver CityPASS®: Admission to Top 3, 4, or 5 Denver Attractions
Continental Divide

Breckenridge Ultimate Full Day Mountain Tour from Denver

CA $192
per adult
98% of travellers recommend
Breckenridge Ultimate Full Day Mountain Tour from Denver
Archery Dodgeball Indoor Attraction Ticket

Denver: Archery Dodgeball Indoor Attraction Ticket

CA $49
per adult
Denver: Archery Dodgeball Indoor Attraction Ticket
See all activities in Denver
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.