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 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

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 ￥17,079
￥42,717 total
includes taxes & fees
Oct 6 - Oct 7
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 ￥15,360
￥49,010 total
includes taxes & fees
Oct 6 - Oct 7
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.
Timbers 9-4 New, spacious condo in Fraser, private deck and more!
Private hot tub with beautiful mountain views and outdoor seating

4. RidgeView Retreat | Steps to Hideaway Park & Town

RidgeView Retreat | Steps to Hideaway Park & Town
Winter Park
The price is ￥18,412
￥67,197 total
includes taxes & fees
Nov 3 - Nov 4
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 ￥11,050
￥55,766 total
includes taxes & fees
Nov 4 - Nov 5
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.
The price is ￥15,204
￥40,207 total
includes taxes & fees
Oct 18 - Oct 19
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.
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 price is ￥28,811
￥87,405 total
includes taxes & fees
Oct 18 - Oct 19
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 ￥24,609
￥70,539 total
includes taxes & fees
Oct 17 - Oct 18
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.
The price is ￥21,310
￥59,862 total
includes taxes & fees
Oct 18 - Oct 19
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 ￥33,606
￥95,763 total
includes taxes & fees
Oct 6 - Oct 7
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 ￥29,663
￥87,856 total
includes taxes & fees
Oct 28 - Oct 29
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
881 Ermine Lane Outdoor hot tub, forest views, new construction vaulted ceilings
A cozy living room with a fireplace, leather sofa, and large windows offering a view of the mountains.

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.
The price is ￥33,810
￥71,113 total
includes taxes & fees
Nov 3 - Nov 4
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 ￥21,941
￥79,338 total
includes taxes & fees
Oct 6 - Oct 7
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.
The price is ￥25,706
￥62,292 total
includes taxes & fees
Oct 6 - Oct 7
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 ￥29,439
￥66,665 total
includes taxes & fees
Oct 11 - Oct 12
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 ￥26,835
￥75,016 total
includes taxes & fees
Oct 20 - Oct 21
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

The Vintage Hotel

The Vintage Hotel

10/10 Excellent
"Great place! Look forward to going again!"
Devon 2-night trip
Posted 2 hours ago
The Vintage Hotel

Find out more about Winter Park

Winter Park Vacation Homes information

Number of reviews
35
Accommodation
714 Vacation Homes
Lowest Price
￥40,207
Highest Price
￥95,763