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

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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

Our top choices for Winter Park vacation homes

A wooden deck with two chairs and a white railing.

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

Hideaway Village Alpine 4 Split interior 2 bedroom, comfortable family rental
Hideaway Village
9.2 out of 10, Wonderful, (11 reviews)
"Great property. Parking lot and walk ways very well maintained. Host was great."
United States
S S.
The price is AED 397
AED 986 total
includes taxes & fees
4 Oct - 5 Oct
Hideaway Village Alpine 4 Split interior 2 bedroom, comfortable family rental
A snow-covered residential area with multiple two-story buildings, a clear sky, and snow-capped mountains in the background.

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

Timbers 5-2 Luxurious 2 bedroom, private deck, forest view
Fraser
10.0 out of 10, Exceptional, (3 reviews)
"Good location, nice place. "
United States
ann b.
The price is AED 357
AED 1,140 total
includes taxes & fees
4 Oct - 5 Oct
Timbers 5-2 Luxurious 2 bedroom, private deck, forest view
A residential area with multi-story buildings, a mountain backdrop, and a clear sky.

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

Timbers 9-4 New, spacious condo in Fraser, private deck and more!
Fraser
8.0 out of 10, Very good, (1 review)
"The unit was clean and well appointed"
United States
Michael J.
The price is AED 385
AED 1,177 total
includes taxes & fees
4 Oct - 5 Oct
Timbers 9-4 New, spacious condo in Fraser, private deck and more!
A bedroom with a bed, wooden headboard, a ceiling fan, a nightstand, a bedside lamp, a window with blinds, and a desk with a chair.

4. RidgeView Retreat | Steps to Hideaway Park & Town

RidgeView Retreat | Steps to Hideaway Park & Town
Winter Park
RidgeView Retreat | Steps to Hideaway Park & Town
A modern two-story house with a balcony, a staircase, and a chimney.

5. 2BR townhouse w/ Byers Peak views

2BR townhouse w/ Byers Peak views
Fraser
8.0 out of 10, Very good, (3 reviews)
"Host communication was excellent. Unit location was excellent for the scenic views. Hot tubs were not in good working condition. Overall it was a great stay."
United States
Jocelyn R.
The price is AED 257
AED 1,309 total
includes taxes & fees
18 Oct - 19 Oct
2BR townhouse w/ Byers Peak views
A cozy living room with a stone fireplace, wooden walls, a green sofa, and a view of a forest through large windows.

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

Hideaway Village Lenado 4 Lovely townhome, river views, 2 private decks
Hideaway Village
8.0 out of 10, Very good, (3 reviews)
"This location is fantastic. The house is dated and floors creak, but it fit our needs."
United States
Cambammo C.
Hideaway Village Lenado 4 Lovely townhome, river views, 2 private decks
A wooden deck with a railing, a covered seating area, and a view of neighboring houses.

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

Close to slopes-Walk to Downtown Winter Park!
Winter Park
9.4 out of 10, Exceptional, (11 reviews)
"great location"
United States
Thomas B.
The price is AED 421
AED 1,213 total
includes taxes & fees
7 Oct - 8 Oct
Close to slopes-Walk to Downtown Winter Park!
A log cabin interior with a stone fireplace, a blue sofa, and a red armchair.

8. The Grand Timberglass Lodge | Tipi | Hot Tub

The Grand Timberglass Lodge | Tipi | Hot Tub
Winter Park
10.0 out of 10, Exceptional, (2 reviews)
"We had such a wonderful stay! We really liked this place. The highlight was definitely the breathtaking views - especially from the hot tub overlooking the mountains. Sauna was fantastic!! We will definitely be returning!! Thank you for sharing your home!!"
United States
Alan W.
The Grand Timberglass Lodge | Tipi | Hot Tub
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.

9. 404 Doc Susie home Delightful and renovated home, walk to downtown, mt views

404 Doc Susie home Delightful and renovated home, walk to downtown, mt views
Downtown
The price is AED 573
AED 1,625 total
includes taxes & fees
4 Oct - 5 Oct
404 Doc Susie home Delightful and renovated home, walk to downtown, mt views
A balcony with two chairs, a view of a building with a red roof, and a clear sky.

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

Mountain escape, minutes from Winter Park resort and town. Hot tub access.
Winter Park
9.6 out of 10, Exceptional, (7 reviews)
"Excellent stay!!"
United States
Ted W.
Mountain escape, minutes from Winter Park resort and town. Hot tub access.
A spacious kitchen with wooden cabinets, a central island, and pendant lighting.

11. Bear Crossing 995 Luxurious 3 bed, private hot tub, views, 1 car garage parking

Bear Crossing 995 Luxurious 3 bed, private hot tub, views, 1 car garage parking
Bear Crossing
10.0 out of 10, Exceptional, (2 reviews)
"Fantastic property. Great location just far enough away from the main strip in Winter Park to be quiet, but close enough to pop right into town. A useable garage was definitely a bonus."
United States
Kevin
The price is AED 782
AED 2,228 total
includes taxes & fees
4 Oct - 5 Oct
Bear Crossing 995 Luxurious 3 bed, private hot tub, views, 1 car garage parking
An outdoor patio with a table and chairs, a grill, and a wooden deck.

12. Needles Eye 1 outstanding mt view private deck vaulted ceiling sleep 8

Needles Eye 1 outstanding mt view private deck vaulted ceiling sleep 8
Fraser
Needles Eye 1 outstanding mt view private deck vaulted ceiling sleep 8
Where mountain views meet cozy evening ambiance.

13. Fresh Tracks @ Peak View Ridge

Fresh Tracks @ Peak View Ridge
Winter Park
10.0 out of 10, Exceptional, (5 reviews)
"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...
United States
Jennifer
The price is AED 686
AED 2,040 total
includes taxes & fees
26 Oct - 27 Oct
Fresh Tracks @ Peak View Ridge
A modern living room with a stone fireplace, a flat-screen TV, and a large sliding glass door to the outdoors.

14. Walkable Winter Park Gem I Downtown + Amenities

Walkable Winter Park Gem I Downtown + Amenities
Winter Park
10.0 out of 10, Exceptional, (1 review)
Walkable Winter Park Gem I Downtown + Amenities
A covered outdoor area with wooden beams and a gravel ground, a trash bin, and a building in the background.

15. 881 Ermine Lane Outdoor hot tub, forest views, new construction vaulted ceilings

881 Ermine Lane Outdoor hot tub, forest views, new construction vaulted ceilings
Fraser
The price is AED 590
AED 1,064 total
includes taxes & fees
2 Nov - 3 Nov
881 Ermine Lane Outdoor hot tub, forest views, new construction vaulted ceilings
A room with a wooden floor, a bench, a sliding glass door to a deck, and a television on the wall.

16. 534 Sun River #8 Wonderful Fraser 2 bedroom, pet friendly, large yard

534 Sun River #8 Wonderful Fraser 2 bedroom, pet friendly, large yard
Downtown
8.6 out of 10, Excellent, (8 reviews)
"The property was amazing the view from the deck of the mountains had a spectacular sunset view. The home is very comfortable and welcoming we had a great evening making dinner and playing board games, the night we didn't cook there were plenty of great places a walk or short drive away, we highly recommend this place for your next stay and adventure at winter park."
United States
Steve P.
534 Sun River #8 Wonderful Fraser 2 bedroom, pet friendly, large yard
A wooden deck with a table and chairs, overlooking a scenic landscape with mountains and trees.

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

Epic Sunset Deck, Panoramic Mountain View’s. Ski, Hike, Bike, & Fish Winter Park
Fraser
10.0 out of 10, Exceptional, (11 reviews)
"Great location! Comfortable beds! Responsive host! Would definitely stay again! "
United States
Pamela D.
The price is AED 511
AED 1,834 total
includes taxes & fees
2 Nov - 3 Nov
Epic Sunset Deck, Panoramic Mountain View’s. Ski, Hike, Bike, & Fish Winter Park
A kitchen with wooden cabinets, stainless steel appliances, a granite countertop, and a window with a view of trees.

18. Meadow Ridge Court 29 unit 8 Lovely and spacious 3 bedroom family condo rental

Meadow Ridge Court 29 unit 8 Lovely and spacious 3 bedroom family condo rental
Fraser
6.0 out of 10, (1 review)
"At 1st glance the place looked pretty good. After getting settled in we found the place could use some tlc. Nothing major that ruined the stay but I was expecting more. Overall I would still recommend after it gets the attention it needs.The people I was in contact with were very friendly and helpful. "
United States
Rodney W.
Meadow Ridge Court 29 unit 8 Lovely and spacious 3 bedroom family condo rental
A lakeside hotel with multiple buildings, a wooden deck, and a view of the lake and mountains.

19. Waterside West B301 Large wrap around deck beautiful view of sunsets Byers Peak

Waterside West B301 Large wrap around deck beautiful view of sunsets Byers Peak
Fraser
10.0 out of 10, Exceptional, (2 reviews)
The price is AED 685
AED 1,551 total
includes taxes & fees
11 Oct - 12 Oct
Waterside West B301 Large wrap around deck beautiful view of sunsets Byers Peak
An indoor swimming pool with a view of trees, a poolside seating area, and a covered patio.

20. Cozy Mountain Getaway Next to Chairlift I Winter Park

Cozy Mountain Getaway Next to Chairlift I Winter Park
Winter Park
9.6 out of 10, Exceptional, (4 reviews)
"It was just perfect setting . I felt as if we were in a tree house."
United States
Diane T.
The price is AED 657
AED 1,725 total
includes taxes & fees
25 Oct - 26 Oct
Cozy Mountain Getaway Next to Chairlift I 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.
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Top Winter Park Hotel Reviews

Gravity Haus Winter Park

Gravity Haus Winter Park

10/10 Excellent
"Great location and amenities."
Paul 1-night trip
Posted 15 hours ago
Gravity Haus Winter Park