Winter Park Highlands Vacation Packages 2026 from $377

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Your Winter Park Highlands Vacation

Our Winter Park Highlands vacation packages are a speedy and practical way to organize and book your next retreat. Uncover the magic of this unique neighborhood without the burden of planning everything yourself. Plan enough time to visit leading nearby sights like Pole Creek Golf Club during your trip to Winter Park Highlands. Expedia can help turn your ideal Winter Park Highlands vacation into reality, no matter your travel plans or budget.

The Latest Winter Park Highlands Vacation Packages

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

Glenwood Springs Inn

Downtown

Save 100% on your flight

$377

per person

Dec 3 - Dec 9

found 7 hours ago

Roundtrip flight included

Atlanta (ATL) to Denver (DEN)

8.8/10 Excellent! (1,614 reviews)

The Green Mountain Falls Lodge

Save 100% on your flight

$404

per person

Dec 8 - Dec 15

found 22 hours ago

Roundtrip flight included

Atlanta (ATL) to Denver (DEN)

8.4/10 Very Good! (311 reviews)

Eagle Point Resort

Matterhorn Village

$1,306

per person

Jan 14 - Jan 19

found 1 day ago

Roundtrip flight included

Miami (MIA) to Denver (DEN)

8.6/10 Excellent! (616 reviews)

Kindred Resort a RockResort

River Run

Save 100% on your flight

$1,879

per person

Jan 3 - Jan 10

found 12 hours ago

Roundtrip flight included

Atlanta (ATL) to Denver (DEN)

9.4/10 Exceptional! (47 reviews)

Village at Breckenridge, A Vail Resorts Property

Historic District

Save 100% on your flight

$887

per person

Jan 10 - Jan 16

found 1 day ago

Roundtrip flight included

Atlanta (ATL) to Denver (DEN)

8.4/10 Very Good! (2,130 reviews)

The condo itself was fine though a couple things were broken. The check-in process was an absolute nightmare. The directions for getting to parking, check-in keys, finding the pool/hot tubs, etc. was awful

Reviewed on Oct 24, 2026

Where to stay in Winter Park Highlands

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

Pole Creek Meadows

If you're looking for some top things to see and do in Pole Creek Meadows and surrounding area, you can visit Pole Creek Golf Club and Ski Granby Ranch.

A snow-capped mountain with a clear sky.

Grand Country Estates

While there might not be top attractions in Grand Country Estates, you can explore the larger area and discover places like Pole Creek Golf Club and Ski Granby Ranch.

Grand View Highlands

If you're looking for some top things to see and do in Grand View Highlands and surrounding area, you can visit Pole Creek Golf Club and Ski Granby Ranch.

Alpine Acres

When in Alpine Acres, you can plan a visit to Pole Creek Golf Club and Ski Granby Ranch, some noteworthy sights in the nearby area.

A winding road through a snowy mountainous landscape at dusk.

Pole Creek

Though Pole Creek might not have many top sights, you can venture to the surrounding area to see attractions like Pole Creek Golf Club and Fraser Valley Library.

Winter Park Highlands Hotel Deals

The Vintage Hotel

100 Winter Park Dr Winter Park CO

$106 nightly

$120 total

Oct 27 - Oct 28

Total with taxes and fees

8.8/10 Excellent! (1,007 reviews)

"Loved the room. Set up was great. Fireplace perfect. Only down side was it took forever to get HOT water. We will return. Thanks for everything."

Reviewed on Oct 25, 2026

YMCA of the Rockies Snow Mountain Ranch

1101 Co Rd 53 Granby CO

Fully refundableReserve now, pay when you stay

$109 nightly

$116 total

Oct 27 - Oct 28

Total with taxes and fees

The Gateway Inn

120 Lake Avenue Grand Lake CO

Fully refundableReserve now, pay when you stay

$79 nightly

$88 total

Nov 1 - Nov 2

Total with taxes and fees

9.2/10 Wonderful! (1,002 reviews)

"Will be back! Had a great time!"

Reviewed on Oct 24, 2026

See all 3,679 properties in Winter Park Highlands

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.