Winter Park Holidays

Photo by Winter Park Resort

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Winter Park Flight & Hotel Packages

Price found within the past 48 hours. Click for updated prices.
Sonesta Denver Downtown

Sonesta Denver Downtown

4 out of 5
Downtown Denver
Price was S$1,059, price is now S$859 per person
S$859
per person
10 Oct - 13 Oct
found 1 day ago
Return flight included
Houston (HOU) to Denver (DEN)
8.2/10 Very Good! (1,906 reviews)
Thanks for a great stay!

Reviewed on 27 Aug, 2025

The Oxford Hotel

The Oxford Hotel

4 out of 5
LoDo
Price was S$1,615, price is now S$1,277 per person
S$1,277
per person
10 Oct - 13 Oct
found 1 day ago
Return flight included
Houston (HOU) to Denver (DEN)
9.4/10 Exceptional! (1,001 reviews)
Gorgeous hotel. Beautiful decor. Spacious rooms. Comfortable beds. Delicious breakfast! Very nice staff.

Reviewed on 28 Aug, 2025

The Crawford Hotel

The Crawford Hotel

5 out of 5
LoDo
Price was S$1,615, price is now S$1,277 per person
S$1,277
per person
10 Oct - 13 Oct
found 1 day ago
Return flight included
Houston (HOU) to Denver (DEN)
9.4/10 Exceptional! (1,003 reviews)
Good central stay. Staff are lovely. Recommend asking for a room that doesn’t t overlook the station though - that was the only thing I didn’t like, thankfully the sound proofing worked perfectly and we didn’t hear a single train.

Reviewed on 25 Aug, 2025

Halcyon - a hotel in Cherry Creek

Halcyon - a hotel in Cherry Creek

4.5 out of 5
Cherry Creek
Price was S$1,428, price is now S$1,146 per person
S$1,146
per person
10 Oct - 13 Oct
found 1 day ago
Return flight included
Houston (HOU) to Denver (DEN)
9.2/10 Wonderful! (1,002 reviews)
Always easy, fun and cool

Reviewed on 18 Aug, 2025

Hilton Denver City Center

Hilton Denver City Center

4 out of 5
Downtown Denver
Price was S$1,255, price is now S$1,019 per person
S$1,019
per person
10 Oct - 13 Oct
found 1 day ago
Return flight included
Houston (HOU) to Denver (DEN)
8.6/10 Excellent! (1,013 reviews)
Stayed in room 538..don't know if they all have exact same design build but shower was not a 3x3 walk in as advertised..more like a 1.5 x 2.5 rectangle. Only a cloth curtain and a foam bumper kept the bathroom from being flooded. UnFortunately our bumper was coming up in multiple places and we had to fight with ever towel we had and more to keep from water damage. Told staff..did nothing.

Reviewed on 26 Aug, 2025

Where to stay in Winter Park

Find the best Winter Park areas and neighborhoods for the activities you enjoy most. Learn more about Winter Park
Default Image

Old Town Winter Park

If you're looking for some top things to see and do in Old Town Winter Park and surrounding area, you can visit Winter Park Ski Resort and Trestle Bike Park.

Find hotels in Old Town Winter Park

Top hotels in Winter Park

The Vintage Hotel

The Vintage Hotel

3 out of 5
100 Winter Park Dr, Winter Park, CO
The price is S$180 per night from 21 Sept to 22 Sept
S$180
per night
21 Sept - 22 Sept
8.6/10 Excellent! (1,010 reviews)
"We went to the winter park Tacos and Margs festival. The Vintage Hotel was great for location and a great night sleep with mountain air."

Reviewed on 25 Aug, 2025

The Vintage Hotel
Gravity Haus Winter Park

Gravity Haus Winter Park

3.5 out of 5
78869 US-40, Winter Park, CO
Fully refundableReserve now, pay when you stay
Get rates
Gravity Haus Winter Park
A Frame Club

A Frame Club

3.5 out of 5
1008 Winter Park Dr, Winter Park, CO
The price is S$433 per night from 28 Sept to 29 Sept
S$433
per night
28 Sept - 29 Sept
A Frame Club
See all 2,297 properties in Winter Park
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

Moffat Tunnel West Portal

You can learn about the history of Winter Park with a stop at Moffat Tunnel West Portal. Discover the mountain views in this quaint area or enjoy its ski slopes.

Moffat Tunnel West Portal

Frequently asked questions

How much does a Winter Park holiday package cost?
Offering great value package deals from S$859 on Expedia, you'll be surprised at how little a holiday to Winter Park costs! Expedia's packages mean less travel planning for you and greater savings.
What are the cheapest months to go to Winter Park?
You can typically find lower rates and better availability in May, October and November. Explore our cheap Winter Park holiday packages and you could land some excellent off-season deals.
How many days is enough for Winter Park?
With about 2 days, you'll have enough time to enjoy popular neighbourhoods like Old Town Winter Park and Bear Crossing during your Winter Park holiday. Be sure to also add Trestle Bike Park and The Fraser River Trail to your must-see list. Looking for more adventures? Consider exploring outside of Winter Park on tours and day trips.
Is it worth booking a holiday package to Winter Park?
Winter Park is a good holiday destination with attractions like Trestle Bike Park among the many things to keep you busy. Whether you're heading away with the family or getting away with friends, a Winter Park holiday promises fun for everyone.
How to find the best Winter Park package deals?
Begin your search for a Winter Park package deal by entering your preferred travel dates and destination under our "Packages" tab. Then select a few filters, like "Property type" and "Amenities," to fine-tune the results to your exact style. You can also sort by "Package discount" and discover offers that come with huge savings. If you don't find the ideal Winter Park package deal straight away, just switch up your dates and search again. Bear in mind that deals are only available for a limited time, so book early and get your Winter Park adventure underway.
Is it cheaper to book a Winter Park holiday as a package?
You can enjoy significant savings on your next Winter Park getaway by booking a personalised holiday package. Check the "Package" heading, then select your travel dates and destination to view some great airfares and hotel prices. Bundling can save travellers hundreds of dollars. Consider adding a rental car and you may score a better deal.
When to book a holiday package to Winter Park?
If you have your Winter Park travel dates locked in, book as soon as you can to bag some terrific deals. With Expedia, you can often reserve some flights up to a year in advance. Prefer spontaneous getaways? Our last-minute deals are perfect for quick escapes.
How to plan a trip to Winter Park?

  1. Choose your travel dates: The things you want to do in Winter Park and your preferred season will help you decide when to get away.
  2. Calculate your budget: Make sure you have enough money to pay for everything from meals and transportation to activities and airfares. Your accommodation will probably be the biggest expense during your trip to Winter Park.
  3. Work out your trip length: Consider how long you'd like to spend discovering Winter Park. Plan your days so you can get to all the activities and attractions you're interested in at a leisurely pace.
  4. Combine your accommodation and airfare: After you've settled on your dates and duration, book the right Winter Park holiday package for you.

* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages. Book Flight + Lodging, save up to 100% of flight price - Savings based on flight + lodging package prices as compared to the price of the same components available for booking separately before all discounts and rewards applied. Your bundled savings cover up to 100% of your flight. Savings vary based on origin/destination, length of trip, stay dates and travel suppliers. Savings not available on all flight + lodging package bookings.