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

Search Vacation Homes in Winter Park

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

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
14 Oct - 15 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
14 Oct - 15 Oct
Timbers 5-2 Luxurious 2 bedroom, private deck, forest view
A modern two-story house with a balcony, a staircase, and a chimney.

3. 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 270
AED 1,329 total
includes taxes & fees
25 Oct - 26 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.

4. 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.
The price is AED 354
AED 928 total
includes taxes & fees
15 Oct - 16 Oct
Hideaway Village Lenado 4 Lovely townhome, river views, 2 private decks
A residential area with multi-story buildings, a mountain backdrop, and a clear sky.

5. 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
14 Oct - 15 Oct
Timbers 9-4 New, spacious condo in Fraser, private deck and more!
A wooden deck with a railing, a covered seating area, and a view of neighboring houses.

6. 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 400
AED 1,199 total
includes taxes & fees
19 Oct - 20 Oct
Close to slopes-Walk to Downtown Winter Park!
A modern kitchen with wooden cabinets, a dining area with a wooden table and chairs, and a view of the outdoors through a window.

7. RidgeView Retreat | Steps to Hideaway Park & Town

RidgeView Retreat | Steps to Hideaway Park & Town
Winter Park
10.0 out of 10, Exceptional, (1 review)
"A perfectly located townhome! A beautiful view from every window and a walk away from various food and trails/creeks. Would love to go back!"
United States
Martyna S.
The price is AED 428
AED 1,564 total
includes taxes & fees
28 Oct - 29 Oct
RidgeView Retreat | Steps to Hideaway Park & Town
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 price is AED 575
AED 1,928 total
includes taxes & fees
27 Oct - 28 Oct
The Grand Timberglass Lodge | Tipi | Hot Tub
A balcony with two chairs, a view of a building with a red roof, and a clear sky.

9. 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.
The price is AED 489
AED 1,385 total
includes taxes & fees
14 Oct - 15 Oct
Mountain escape, minutes from Winter Park resort and town. Hot tub access.
An indoor swimming pool with a view of trees, a poolside seating area, and a covered patio.

10. 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 558
AED 1,691 total
includes taxes & fees
19 Oct - 20 Oct
Cozy Mountain Getaway Next to Chairlift I Winter Park
A modern living room with a fireplace, a sofa, a coffee table, and a dining area with chairs and a table.

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

Private Hot Tub, Garage + EV Charger, On Bus Line!
Fraser
10.0 out of 10, Exceptional, (3 reviews)
"The hot tub was great after a day of snowboarding!"
United States
Kale S.
The price is AED 465
AED 1,293 total
includes taxes & fees
14 Oct - 15 Oct
Private Hot Tub, Garage + EV Charger, On Bus Line!
Where mountain views meet cozy evening ambiance.

12. Fresh Tracks @ Peak View Ridge

Fresh Tracks @ Peak View Ridge
Winter Park
10.0 out of 10, Exceptional, (5 reviews)
"Fresh Tracks @ Peak View Ridge will not disappoint! A brand new property, in pristine condition, with everything you could need! Host was very communicative and offered to assist if we were to need it, and the cleaning staff did a wonderful job preparing for us! Close to everything but not right on the main busy street in town. We absolutely loved the location and view! Can’t wait to stay here again!"
United States
Corrie W.
The price is AED 615
AED 1,953 total
includes taxes & fees
14 Oct - 15 Oct
Fresh Tracks @ Peak View Ridge
A covered outdoor area with wooden beams and a gravel ground, a trash bin, and a building in the background.

13. 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 580
AED 1,053 total
includes taxes & fees
1 Nov - 2 Nov
881 Ermine Lane Outdoor hot tub, forest views, new construction vaulted ceilings
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

Hot tub, 3 bedroom, Ski friendly, New build, 5 star Luxury Retreat
Winter Park
10.0 out of 10, Exceptional, (1 review)
"Very well kept and well equipped. Excellent communication with owners. Very responsive to questions. Location is close to ski shuttle. 3 car covered garage. Hot tub A++++ Will stay again."
United States
Candice
Hot tub, 3 bedroom, Ski friendly, New build, 5 star Luxury Retreat
A wooden deck with a table and chairs, overlooking a scenic landscape with mountains and trees.

15. 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
14 Oct - 15 Oct
Epic Sunset Deck, Panoramic Mountain View’s. Ski, Hike, Bike, & Fish Winter Park
A spacious living room with a stone fireplace, a dining area with a wooden table and chairs, and a large window offering a view of the outdoors.

16. Family-Friendly 3BR Mountain Condo – Pool, Hot Tub, Gym Near Winter Park

Family-Friendly 3BR Mountain Condo – Pool, Hot Tub, Gym Near Winter Park
Downtown
10.0 out of 10, Exceptional, (2 reviews)
"Perfect place to stay with young kids. Very baby friendly with all the essentials. Great communication with hosts. Has everything you need for your stay. Highly recommend! "
United States
Ashley L.
The price is AED 583
AED 1,543 total
includes taxes & fees
14 Oct - 15 Oct
Family-Friendly 3BR Mountain Condo – Pool, Hot Tub, Gym Near Winter Park
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

Walkable Winter Park Gem I Downtown + Amenities
Winter Park
10.0 out of 10, Exceptional, (1 review)
The price is AED 741
AED 1,890 total
includes taxes & fees
14 Oct - 15 Oct
Walkable Winter Park Gem I Downtown + Amenities
A living room with a fireplace, a sofa, a coffee table, and a view of mountains through a glass door.

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

The AlpenGlow House: Private Hot Tub Retreat with Stunning Mountain Views!
Rendezvous
10.0 out of 10, Exceptional, (18 reviews)
"Amazing stay!!! Everything was as advertised!!Highly recommend!!"
United States
RW L.
The price is AED 579
AED 1,873 total
includes taxes & fees
20 Oct - 21 Oct
The AlpenGlow House: Private Hot Tub Retreat with Stunning Mountain Views!
A spacious kitchen with wooden cabinets, a central island, and pendant lighting.

19. 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
14 Oct - 15 Oct
Bear Crossing 995 Luxurious 3 bed, private hot tub, views, 1 car garage parking
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.

20. 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
14 Oct - 15 Oct
404 Doc Susie home Delightful and renovated home, walk to downtown, mt views
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Winter Park Hotel Reviews

Fraser Crossing Founders Pointe

Fraser Crossing Founders Pointe

8/10 Good
"It was our first‑year anniversary, and we chose this spot for our celebration. Even though we didn’t realize many things would be closed for the season, we still had a wonderful time. The area is beautiful — the colors of the trees, the fresh air, and the overall atmosphere were truly breathtaking. I would have given 5 stars, but on our last night we had no hot water and couldn’t enjoy the hot tub before leaving, which had been one of our favorite parts on the first day. We didn’t know what was going on until we saw a note in the elevator stating that the boiler was down until 10/11/2026. That was very disappointing, as we couldn’t enjoy a hot tub soak or even a nice hot shower before heading home. Overall, we enjoyed our stay, but the unexpected lack of hot water on the final night did affect our experience a little."
Tracey 3-night trip
Posted 14 hours ago
Fraser Crossing Founders Pointe