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
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

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
9.0 out of 10, Wonderful, (10 reviews)
"Great property. Parking lot and walk ways very well maintained. Host was great."
United States
S S.
The price is ￥17,036
￥42,280 total
includes taxes & fees
Sep 26 - Sep 27
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, (2 reviews)
"Good location, nice place. "
United States
ann b.
The price is ￥15,321
￥48,886 total
includes taxes & fees
Sep 25 - Sep 26
Timbers 5-2 Luxurious 2 bedroom, private deck, forest view

3. 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 ￥26,836
￥84,536 total
includes taxes & fees
Sep 30 - Oct 1
Fresh Tracks @ Peak View Ridge
A modern living room with a fireplace, a sofa, a coffee table, and a dining area with chairs and a table.

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

5. 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 ￥24,546
￥69,660 total
includes taxes & fees
Sep 25 - Sep 26
404 Doc Susie home Delightful and renovated home, walk to downtown, mt views
A residential area with multi-story buildings, a mountain backdrop, and a clear sky.

6. 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 ￥16,517
￥50,288 total
includes taxes & fees
Oct 7 - Oct 8
Timbers 9-4 New, spacious condo in Fraser, private deck and more!
A living room with a fireplace, a sofa, a coffee table, and a view of mountains through a glass door.

7. 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 ￥24,215
￥79,021 total
includes taxes & fees
Oct 1 - Oct 2
The AlpenGlow House: Private Hot Tub Retreat with Stunning Mountain Views!
A wooden deck with a railing, a covered seating area, and a view of neighboring houses.

8. 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)
"Pet friendly, great location and covered parking"
United States
Jennifer H.
The price is ￥16,698
￥50,454 total
includes taxes & fees
Sep 28 - Sep 29
Close to slopes-Walk to Downtown Winter Park!
A modern two-story house with a balcony, a staircase, and a chimney.

9. 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 ￥11,079
￥55,914 total
includes taxes & fees
Oct 18 - Oct 19
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.

10. 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 ￥15,166
￥40,106 total
includes taxes & fees
Sep 27 - Sep 28
Hideaway Village Lenado 4 Lovely townhome, river views, 2 private decks
A modern living room with a sofa, a coffee table, and a TV mounted on the wall.

11. 4BR Mountain Escape | Family Friendly | Hot Tub

4BR Mountain Escape | Family Friendly | Hot Tub
Winter Park
9.8 out of 10, Exceptional, (16 reviews)
"Wonderful accommodations for our family. It had everything we needed. We really enjoyed our stay and hope to stay again in the future."
United States
Shannon R.
The price is ￥29,286
￥137,468 total
includes taxes & fees
Sep 27 - Sep 28
4BR Mountain Escape | Family Friendly | Hot Tub
A balcony with two chairs, a view of a building with a red roof, and a clear sky.

12. 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 ￥25,979
￥65,057 total
includes taxes & fees
Oct 7 - Oct 8
Mountain escape, minutes from Winter Park resort and town. Hot tub access.
A log cabin interior with a stone fireplace, a blue sofa, and a red armchair.

13. 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 ￥25,337
￥83,408 total
includes taxes & fees
Oct 7 - Oct 8
The Grand Timberglass Lodge | Tipi | Hot Tub
A wooden deck with a table and chairs, overlooking a scenic landscape with mountains and trees.

14. 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 ￥21,886
￥78,612 total
includes taxes & fees
Oct 4 - Oct 5
Epic Sunset Deck, Panoramic Mountain View’s. Ski, Hike, Bike, & Fish Winter Park
An indoor swimming pool with a view of trees, a poolside seating area, and a covered patio.

15. 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 ￥19,681
￥66,918 total
includes taxes & fees
Sep 28 - Sep 29
Cozy Mountain Getaway Next to Chairlift I Winter Park
A two-story house with a covered patio, a garage, and a small attached shed.

16. 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 ￥24,581
￥46,594 total
includes taxes & fees
Oct 4 - Oct 5
881 Ermine Lane Outdoor hot tub, forest views, new construction vaulted ceilings
A modern living room with a stone fireplace, blue sofas, and a large window overlooking a snowy landscape.

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

Spacious, Updated Mountain Home with Views, Private Hot Tub and Sauna.
Fraser
10.0 out of 10, Exceptional, (1 review)
"Stayed here for our trip to Winter Park. Layout of the home was my favorite! It was the perfect location. We loved it and hope to come back."
United States
Crystal F.
The price is ￥24,940
￥83,171 total
includes taxes & fees
Sep 27 - Sep 28
Spacious, Updated Mountain Home with Views, Private Hot Tub and Sauna.
A modern living room with a stone fireplace, a flat-screen TV, and a large sliding glass door to the outdoors.

18. 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 kitchen with wooden cabinets, stainless steel appliances, a granite countertop, and a window with a view of trees.

19. 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.
The price is ￥25,641
￥61,632 total
includes taxes & fees
Sep 25 - Sep 26
Meadow Ridge Court 29 unit 8 Lovely and spacious 3 bedroom family condo rental
A spacious kitchen with wooden cabinets, a central island, and pendant lighting.

20. 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 ￥33,521
￥95,520 total
includes taxes & fees
Sep 25 - Sep 26
Bear Crossing 995 Luxurious 3 bed, private hot tub, views, 1 car garage parking
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

The Vintage Hotel

The Vintage Hotel

10/10 Excellent
"Friendly, knowledgeable staff Good Location. Enjoyed our short stay. Parking was close and easy."
Roy 1-night trip
Posted 3 hours ago
The Vintage Hotel

Find out more about Winter Park

Winter Park Vacation Homes information

Number of reviews
71
Accommodation
714 Vacation Homes
Lowest Price
￥40,106
Highest Price
￥137,468