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

Our top choices for Winter Park vacation homes

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

1. 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 ￥15,220
￥40,250 total
includes taxes & fees
Oct 18 - Oct 19
Hideaway Village Lenado 4 Lovely townhome, river views, 2 private decks
A wooden deck with two chairs and a white railing.

2. 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 ￥17,106
￥42,949 total
includes taxes & fees
Oct 18 - Oct 19
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.

3. 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 ￥15,385
￥49,592 total
includes taxes & fees
Oct 18 - Oct 19
Timbers 5-2 Luxurious 2 bedroom, private deck, forest view
A modern two-story house with a balcony, a staircase, and a chimney.

4. 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 ￥11,620
￥56,179 total
includes taxes & fees
Oct 18 - Oct 19
2BR townhouse w/ Byers Peak views
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 ￥16,576
￥51,140 total
includes taxes & fees
Oct 29 - Oct 30
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
9.0 out of 10, Wonderful, (12 reviews)
"great location"
United States
Thomas B.
The price is ￥16,767
￥51,157 total
includes taxes & fees
Oct 21 - Oct 22
Close to slopes-Walk to Downtown Winter Park!
A log cabin interior with a stone fireplace, a blue sofa, and a red armchair.

7. 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 ￥24,758
￥82,664 total
includes taxes & fees
Oct 18 - Oct 19
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.

8. 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 ￥23,241
￥62,102 total
includes taxes & fees
Oct 20 - Oct 21
Mountain escape, minutes from Winter Park resort and town. Hot tub access.
A modern kitchen with wooden cabinets, a dining area with a wooden table and chairs, and a view of the outdoors through a window.

9. 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
Where mountain views meet cozy evening ambiance.

10. 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 ￥24,917
￥82,648 total
includes taxes & fees
Oct 29 - Oct 30
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.

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.
Private Hot Tub, Garage + EV Charger, On Bus Line!
An indoor swimming pool with a view of trees, a poolside seating area, and a covered patio.

12. 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 ￥22,755
￥73,456 total
includes taxes & fees
Oct 18 - Oct 19
Cozy Mountain Getaway Next to Chairlift I Winter Park
A modern kitchen with a central island, a dining area with a sofa, and a large sliding glass door leading to a balcony.

13. 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 ￥24,746
￥76,989 total
includes taxes & fees
Oct 18 - Oct 19
Hot tub, 3 bedroom, Ski friendly, New build, 5 star Luxury Retreat
A living room with a fireplace, a sofa, a coffee table, and a view of mountains through a glass door.

14. 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 ￥24,189
￥79,641 total
includes taxes & fees
Oct 20 - Oct 21
The AlpenGlow House: Private Hot Tub Retreat with Stunning Mountain Views!
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, (12 reviews)
"Great location! Comfortable beds! Responsive host! Would definitely stay again! "
United States
Pamela D.
The price is ￥21,965
￥79,950 total
includes taxes & fees
Oct 26 - Oct 27
Epic Sunset Deck, Panoramic Mountain View’s. Ski, Hike, Bike, & Fish Winter Park
A bedroom with a large window, a wooden wardrobe, a television, and a carpeted floor.

16. 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
The price is ￥36,629
￥121,876 total
includes taxes & fees
Oct 31 - Nov 1
Arrow At Winter Park Unit 294 Outdoor HT, private deck, downtown luxury townhome
A spacious kitchen with wooden cabinets, a central island, and pendant lighting.

17. 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 ￥33,642
￥96,689 total
includes taxes & fees
Oct 18 - Oct 19
Bear Crossing 995 Luxurious 3 bed, private hot tub, views, 1 car garage parking
Your fully equipped kitchen invites culinary adventures with its warm wood cabinetry, modern stainless steel appliances, and bright natural light streaming through large windows overlooking the greenery outside.

18. 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 ￥25,100
￥47,296 total
includes taxes & fees
Oct 19 - Oct 20
881 Ermine Lane Outdoor hot tub, forest views, new construction vaulted ceilings
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.

19. 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 ￥24,635
￥70,614 total
includes taxes & fees
Nov 17 - Nov 18
404 Doc Susie home Delightful and renovated home, walk to downtown, mt views
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.

20. 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 ￥27,309
￥69,101 total
includes taxes & fees
Nov 15 - Nov 16
Family-Friendly 3BR Mountain Condo – Pool, Hot Tub, Gym Near 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

The Trailhead | Beautifully Furnished Modern Condo In Downtown Winter Park

The Trailhead | Beautifully Furnished Modern Condo In Downtown Winter Park

10/10 Excellent
"The best place to stay in Winter Park! The location is great, the property is beautiful and the host is the best! Very responsive when I had a “senior moment” and couldn’t find my check-in instructions. Hated to leave, will definitely be back"
Nancy M. 3-night trip
Posted 13 hours ago
The Trailhead | Beautifully Furnished Modern Condo In Downtown Winter Park

Find out more about Winter Park

Winter Park Vacation Homes information

Number of reviews
84
Accommodation
735 Vacation Homes
Lowest Price
￥40,250
Highest Price
￥121,876