Winter Park, CO Vacation Homes from AED 928

A snow-covered building with illuminated windows and a ski lift in the foreground.

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Our top choices for Winter Park vacation homes

A snow-covered residential area with multiple two-story buildings, a clear sky, and snow-capped mountains in the background.

1. Timbers 5-2 Luxurious 2 bedroom, private deck, forest view

Fraser

ann b.

A wooden deck with two chairs and a white railing.

2. Hideaway Village Alpine 4 Split interior 2 bedroom, comfortable family rental

Hideaway Village

S S.

AED 990 total

includes taxes & fees

14 Oct - 15 Oct

A modern kitchen with stainless steel appliances, wooden cabinets, and a granite countertop.

3. RidgeView Retreat | Steps to Hideaway Park & Town

Winter Park

AED 1,564 total

includes taxes & fees

14 Oct - 15 Oct

A living room with a fireplace, a sofa, a coffee table, and a view of mountains through a glass door.

4. The AlpenGlow House: Private Hot Tub Retreat with Stunning Mountain Views!

Rendezvous

RW L.

A balcony with two chairs, a view of a building with a red roof, and a clear sky.

5. Mountain escape, minutes from Winter Park resort and town. Hot tub access.

Winter Park

Ted W.

AED 1,401 total

includes taxes & fees

14 Oct - 15 Oct

A modern two-story house with a dark exterior, a front door with a curtain, two potted plants, and a driveway leading to a garage.

6. 404 Doc Susie home Delightful and renovated home, walk to downtown, mt views

Downtown

AED 1,625 total

includes taxes & fees

2 Oct - 3 Oct

A residential area with multi-story buildings, a mountain backdrop, and a clear sky.

7. Timbers 9-4 New, spacious condo in Fraser, private deck and more!

Fraser

Michael J.

A covered outdoor area with wooden beams and a gravel ground, a trash bin, and a building in the background.

8. 881 Ermine Lane Outdoor hot tub, forest views, new construction vaulted ceilings

Fraser

A modern two-story house with a balcony, a staircase, and a chimney.

9. 2BR townhouse w/ Byers Peak views

Fraser

Jocelyn R.

AED 1,309 total

includes taxes & fees

18 Oct - 19 Oct

A wooden deck with a railing, a covered seating area, and a view of neighboring houses.

10. Close to slopes-Walk to Downtown Winter Park!

Winter Park

Thomas B.

AED 1,202 total

includes taxes & fees

7 Oct - 8 Oct

A cozy living room with a stone fireplace, wooden walls, a green sofa, and a view of a forest through large windows.

11. Hideaway Village Lenado 4 Lovely townhome, river views, 2 private decks

Hideaway Village

Cambammo C.

AED 928 total

includes taxes & fees

3 Oct - 4 Oct

A modern living room with a sofa, a coffee table, and a TV mounted on the wall.

12. 4BR Mountain Escape | Family Friendly | Hot Tub

Winter Park

Shannon R.

A wooden deck with a table and chairs, overlooking a scenic landscape with mountains and trees.

13. Epic Sunset Deck, Panoramic Mountain View’s. Ski, Hike, Bike, & Fish Winter Park

Fraser

Pamela D.

AED 1,834 total

includes taxes & fees

4 Oct - 5 Oct

A modern kitchen with a central island, a dining area with a sofa, and a large sliding glass door leading to a balcony.

14. Hot tub, 3 bedroom, Ski friendly, New build, 5 star Luxury Retreat

Winter Park

Candice

A log cabin interior with a stone fireplace, a blue sofa, and a red armchair.

15. The Grand Timberglass Lodge | Tipi | Hot Tub

Winter Park

Alan W.

A modern living room with a stone fireplace, blue sofas, and a large window overlooking a snowy landscape.

16. Spacious, Updated Mountain Home with Views, Private Hot Tub and Sauna.

Fraser

Crystal F.

A modern living room with a stone fireplace, a flat-screen TV, and a large sliding glass door to the outdoors.

17. Walkable Winter Park Gem I Downtown + Amenities

Winter Park

Where mountain views meet cozy evening ambiance.

18. Fresh Tracks @ Peak View Ridge

Winter Park

"5/5 Stars – Absolutely Stunning Mountain Retreat! We had an incredible stay at this mountain house and cannot recommend it enough. From the moment we walked in, we were blown away by how immaculately clean the entire property was—it truly felt spotless and welcoming. The interior design is beautiful, perfectly balancing a cozy, mountain vibe with modern, high-end aesthetics. Every room was thoughtfully decorated and furnished for comfort. The amenities were equally impressive; the host provided...

Jennifer

A bedroom with a large bed, two bedside tables, a wooden door, and a window with a view.

19. Red Quill 707 Luxury downtown, private HT, garage parking, walk to main st

Winter Park

AED 2,042 total

includes taxes & fees

14 Oct - 15 Oct

A modern living room with a fireplace, a sofa, a coffee table, and a dining area with chairs and a table.

20. Private Hot Tub, Garage + EV Charger, On Bus Line!

Fraser

Kale S.

AED 1,467 total

includes taxes & fees

6 Oct - 7 Oct

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Top Winter Park Hotel Reviews

Winter Park Chateau

10/10 Excellent

"Love this place everything about it was great. Can’t wait to stay again❣️"

Luxury Downtown Condo - Private Hot Tub! Walk to Dining and Ski Bus...

10/10 Excellent

"The location was great. The house was very clean. The amenities were great from the towels for the hot tub to the well-equipped kitchen. We were a party of 10 and we ate most of our meals because it was comfortable, fun and easy to accommodate all the cooks in the kitchen. We did Elevation Everest, lots of Downhill MTB and hikes. If we ever come back to Winter Park, we will surely stay here again. I forgot my Dyson hairdryer and I’m sure Bob is shipping it back to me now."

A Frame Club

8/10 Good

"Clean and comfortable. Great location, close to action. Super cute. Moose wandered through the property while we were there! The reasons it didn’t get 5 stars: -Breakfast was odd. Pre built burritos, grab and go, for one hour. Tasty, but just odd. -Staff repeatedly told us the restaurant was open for dinner. We sat there for 10 minutes without being acknowledged by anyone. So we left. -No bathroom fan."

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Winter Park vacation homes

1. Timbers 5-2 Luxurious 2 bedroom, private deck, forest view

2. Hideaway Village Alpine 4 Split interior 2 bedroom, comfortable family rental

3. RidgeView Retreat | Steps to Hideaway Park & Town

4. The AlpenGlow House: Private Hot Tub Retreat with Stunning Mountain Views!

5. Mountain escape, minutes from Winter Park resort and town. Hot tub access.

6. 404 Doc Susie home Delightful and renovated home, walk to downtown, mt views

7. Timbers 9-4 New, spacious condo in Fraser, private deck and more!