Winfield Vacation Packages

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

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Top Winfield Vacation Deals

Price found within the past 48 hours. Click for updated prices.
Laurelwood Condominiums

Laurelwood Condominiums

3 out of 5
Price was CA $3,991, price is now CA $3,204 per person
CA $3,204
per person
Dec 28 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Denver (DEN)
9.2/10 Wonderful! (1,577 reviews)
Nice area, quite, didn't seem very busy which was nice. We appreciated the fully stocked kitchen supplies, has everything we could think to need to cook in. The grill was great and easy to use.

Reviewed on Nov 1, 2026

The Plaza Condominiums, A Vail Resorts Property

The Plaza Condominiums, A Vail Resorts Property

3 out of 5
Mount Crested Butte
Price was CA $4,457, price is now CA $3,439 per person
CA $3,439
per person
Dec 28 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Gunnison (GUC)
8.2/10 Very good! (144 reviews)
THe property was advertised as a 3-peak

Reviewed on Sep 27, 2026

Hotel Jerome, Auberge Collection

Hotel Jerome, Auberge Collection

5 out of 5
Downtown Aspen
Price was CA $12,355, price is now CA $9,735 per person
CA $9,735
per person
Jan 20 - Jan 27
found 1 day ago
Roundtrip flight included
Toronto (YYZ) to Denver (DEN)
9.6/10 Exceptional! (487 reviews)

The Gant

The Gant

4 out of 5
East Aspen
Price was CA $14,594, price is now CA $11,627 per person
CA $11,627
per person
Dec 28 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Denver (DEN)
9.6/10 Exceptional! (1,064 reviews)

Stonebridge Inn

Stonebridge Inn

4 out of 5
Price was CA $4,559, price is now CA $3,674 per person
CA $3,674
per person
Dec 28 - Jan 2
found 1 day ago
Roundtrip non-stop flight included
Toronto (YYZ) to Denver (DEN)
8.2/10 Very good! (1,000 reviews)
THE place to be at Snowmass!! Do not hesitate and stay here instead of Aspen if goong for a skiing adventire. Grat locarion, superb dinning at the restaurant a nd within walking distance to the mall

Reviewed on Jul 14, 2026

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Winfield Hotel Deals

Best Western Vista Inn

Best Western Vista Inn

2.5 out of 5
733 U S Highway 24 N Buena Vista CO
Fully refundableReserve now, pay when you stay
The price is CA $273 per night from Nov 8 to Nov 9
CA $273
CA $301 total
Nov 8 - Nov 9
includes taxes & fees
Best Western Vista Inn
Winmar Cabins

Winmar Cabins

2.5 out of 5
1535 U.S. 24 Twin Lakes CO
The price is CA $200 per night from Nov 19 to Nov 20
CA $200
CA $218 total
Nov 19 - Nov 20
includes taxes & fees
8.2/10 Very good! (66 reviews)
"K"

Reviewed on Oct 31, 2026

Winmar Cabins
Buffalo Peaks B&B

Buffalo Peaks B&B

3 out of 5
28928 Fairway Dr Buena Vista CO
The price is CA $219 per night from Nov 23 to Nov 24
CA $219
CA $235 total
Nov 23 - Nov 24
includes taxes & fees
9.8/10 Exceptional! (223 reviews)
"Paz is a wonderful host very accommodating and wonderful. It was a great stay and I will return."

Reviewed on Nov 2, 2026

Buffalo Peaks B&B
See all 211 properties in Winfield
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.
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What to do in Winfield

Anna Maria Island and Bradenton Beach: Parasailing Tour

Anna Maria Island & Bradenton Beach Parasailing Tour

CA $154
per adult
100% of travellers recommend
Anna Maria Island & Bradenton Beach Parasailing Tour
See all activities in Winfield

Frequently asked questions

How much does a Winfield vacation package cost?
You'll find cheap prices from CA $3,204 on Expedia for your Winfield break. However, factors like the length of stay, the season and your choice of hotel will determine how much your vacation to Winfield costs.
What are the cheapest months to go to Winfield?
January, February and April are great times to look for cheap Winfield vacation packages. Choosing to travel in less busy months means you can generally find better prices on flights and hotels.
How many days is enough for Winfield?
With a well-planned itinerary, you can easily tick off the top Winfield sights in a few days. But if you want to discover lesser-known spots or go on day trips, consider booking your Winfield vacation for longer.
How to find the best Winfield package deals?
Finding a cheap Winfield package deal is a breeze with Expedia. Once you've entered your travel dates and destination under our "Packages" tab, set your budget range, apply a couple of filters and browse what's available. You can fine-tune your search by "Amenities," "Property type," "Traveller experience" and more. Order the results by "Price: low to high" to discover the most wallet-friendly Winfield package deals. Want a simple trick to get the biggest savings? Have some flexibility with your departure dates and consider going away on a weekday, when prices are often lower.
Is it cheaper to book a Winfield vacation as a package?
Expedia vacation packages are designed to give you more bang for your buck. Bundle your car rental, flight and hotel into one great-value price and enjoy significant savings. You'll usually get a better deal than booking each component individually. And you'll still enjoy the flexibility to create a tailored Winfield vacation by choosing your preferred type of stay, airline and car class.
When to book a vacation package to Winfield?
Score fantastic discounts by reserving your flights early with Expedia. If spontaneity is more your thing, snap up one of our last-minute deals for an impromptu Winfield trip.
How to plan a trip to Winfield?

  1. Pick your travel dates: The things you want to do in Winfield and your favourite season can help you decide when to go.
  2. Set a budget: Consider costs like flights, food and transportation when calculating how much to save for your trip to Winfield. Then, select a property that fits your budget, whether that's an affordable option or a swankier retreat.
  3. Decide how long to go for: Now that you know more about Winfield, you can figure out the perfect length of your vacation. Put together a rough plan and give yourself enough time to cover everything you want to do.
  4. Combine your accommodations and airfare: After you've nailed down your trip dates and duration, lock in the perfect Winfield vacation package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.