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
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 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, (12 reviews)
"This was a great place for me and my family to stay. The place was clean, and great communication with the host."
United States
Danielle T.
The price is AED 303
AED 1,055 total
includes taxes & fees
12 Nov - 13 Nov
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.
Timbers 5-2 Luxurious 2 bedroom, private deck, forest view
A stone wall with the inscription 'the Timberline' and a small lamp.

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.
Timbers 9-4 New, spacious condo in Fraser, private deck and more!
The base of the ski resort

4. RidgeView Retreat | Steps to Hideaway Park & Town

RidgeView Retreat | Steps to Hideaway Park & Town
Winter Park
10.0 out of 10, Exceptional, (2 reviews)
"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.
RidgeView Retreat | Steps to Hideaway Park & Town
A cozy living room with a stone fireplace, wooden walls, a green sofa, and a view of a forest through large windows.

5. 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 257
AED 990 total
includes taxes & fees
2 Nov - 3 Nov
Hideaway Village Lenado 4 Lovely townhome, river views, 2 private decks
A modern living room with a fireplace, a sofa, a coffee table, and a dining area with chairs and a table.

6. 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.
Private Hot Tub, Garage + EV Charger, On Bus Line!
A kitchen with wooden cabinets, stainless steel appliances, a granite countertop, and a window with a view of trees.

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

8. 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
The price is AED 575
AED 1,786 total
includes taxes & fees
1 Nov - 2 Nov
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.

9. 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, (13 reviews)
"Great location! Comfortable beds! Responsive host! Would definitely stay again! "
United States
Pamela D.
The price is AED 511
AED 1,683 total
includes taxes & fees
1 Nov - 2 Nov
Epic Sunset Deck, Panoramic Mountain View’s. Ski, Hike, Bike, & Fish Winter Park
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!

Close to slopes-Walk to Downtown Winter Park!
Winter Park
9.0 out of 10, Wonderful, (12 reviews)
"great location"
United States
Thomas B.
Close to slopes-Walk to Downtown Winter Park!
Where mountain views meet cozy evening ambiance.

11. 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 520
AED 2,300 total
includes taxes & fees
10 Nov - 11 Nov
Fresh Tracks @ Peak View Ridge
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.

12. 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
404 Doc Susie home Delightful and renovated home, walk to downtown, mt views
A spacious kitchen with wooden cabinets, a central island, and pendant lighting.

13. 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 627
AED 2,289 total
includes taxes & fees
1 Nov - 2 Nov
Bear Crossing 995 Luxurious 3 bed, private hot tub, views, 1 car garage parking
A modern living room with a grey sofa, a wooden coffee table, and a staircase with a wooden finish.

14. 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
881 Ermine Lane Outdoor hot tub, forest views, new construction vaulted ceilings
A balcony with two chairs, a view of a building with a red roof, and a clear sky.

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

16. 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 AlpenGlow House: Private Hot Tub Retreat with Stunning Mountain Views!
A modern kitchen with a large island, stainless steel appliances, and pendant lighting.

17. 47 Lookout Point Rendezvous Spacious & Modern townhome sleeps 10 private hot tub

47 Lookout Point Rendezvous Spacious & Modern townhome sleeps 10 private hot tub
Rendezvous
9.6 out of 10, Exceptional, (9 reviews)
"Clean rooms, hot tub was a little small for 7 adults, overall great experience"
United States
lyn y.
The price is AED 818
AED 2,718 total
includes taxes & fees
1 Nov - 2 Nov
47 Lookout Point Rendezvous Spacious & Modern townhome sleeps 10 private hot tub
A modern kitchen with a central island, stainless steel appliances, and a view to the outdoors.

18. Arrow At Winter Park Unit 294 Outdoor HT, private deck, downtown luxury townhome

Arrow At Winter Park Unit 294 Outdoor HT, private deck, downtown luxury townhome
Winter Park
Arrow At Winter Park Unit 294 Outdoor HT, private deck, downtown luxury townhome
A modern living room with a sectional sofa, a coffee table, a fireplace, and large windows offering a scenic view.

19. 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
A cozy living room with a fireplace, leather sofa, and large windows offering a view of the mountains.

20. 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
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

Winter Park Chateau

Winter Park Chateau

10/10 Excellent
"We had an amazing, relaxing time time. Jon was awesome!"
Jessica 1-night trip
Posted 4 days ago
Winter Park Chateau