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

Holiday Homes in Winter Park

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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 holiday homes

A snow-covered residential area with multiple two-story buildings, a clear sky, and snow-capped mountains in the background.

1. 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 €279
includes taxes & fees
17 Oct - 18 Oct
Timbers 5-2 Luxurious 2 bedroom, private deck, forest view
A cozy living room with a stone fireplace, wooden walls, a green sofa, and a view of a forest through large windows.

2. 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 €233
includes taxes & fees
18 Oct - 19 Oct
Hideaway Village Lenado 4 Lovely townhome, river views, 2 private decks
A wooden deck with two chairs and a white railing.

3. 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 €246
includes taxes & fees
18 Oct - 19 Oct
Hideaway Village Alpine 4 Split interior 2 bedroom, comfortable family rental
A wooden deck with a table and chairs, overlooking a scenic landscape with mountains and trees.

4. 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 €432
includes taxes & fees
17 Oct - 18 Oct
Epic Sunset Deck, Panoramic Mountain View’s. Ski, Hike, Bike, & Fish Winter Park
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 €309
includes taxes & fees
17 Oct - 18 Oct
2BR townhouse w/ Byers Peak views
A spacious kitchen with wooden cabinets, a central island, and pendant lighting.

6. 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 €540
includes taxes & fees
17 Oct - 18 Oct
Bear Crossing 995 Luxurious 3 bed, private hot tub, views, 1 car garage parking
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 €467
includes taxes & fees
18 Oct - 19 Oct
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.

8. 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 €400
includes taxes & fees
13 Nov - 14 Nov
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.

9. 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 €288
includes taxes & fees
17 Oct - 18 Oct
Timbers 9-4 New, spacious condo in Fraser, private deck and more!
A kitchen with wooden cabinets, stainless steel appliances, a granite countertop, and a window with a view of trees.

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

11. 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
A wooden staircase leading to a room with a stone wall.

12. Red Quill 707 Luxury downtown, private HT, garage parking, walk to main st

Red Quill 707 Luxury downtown, private HT, garage parking, walk to main st
Winter Park
The price is €499
includes taxes & fees
17 Oct - 18 Oct
Red Quill 707 Luxury downtown, private HT, garage parking, walk to main st
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)
"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 €476
includes taxes & fees
29 Oct - 30 Oct
Fresh Tracks @ Peak View Ridge
A lakeside hotel with multiple buildings, a wooden deck, and a view of the lake and mountains.

14. 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 €366
includes taxes & fees
17 Oct - 18 Oct
Waterside West B301 Large wrap around deck beautiful view of sunsets Byers Peak
A wooden deck with a railing, a covered seating area, and a view of neighboring houses.

15. 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 €290
includes taxes & fees
20 Oct - 21 Oct
Close to slopes-Walk to Downtown Winter Park!
A kitchen with wooden cabinets, a stainless steel refrigerator, and a marble countertop.

16. 200 Quill Court 4 bedroom home, private HT, 2 living spaces, EV car charger

200 Quill Court 4 bedroom home, private HT, 2 living spaces, EV car charger
Fraser
9.4 out of 10, Exceptional, (3 reviews)
"Love the house and the space was great for my family and it was really clean and had a great view will book again"
United States
tanjalek D.
The price is €626
includes taxes & fees
17 Oct - 18 Oct
200 Quill Court 4 bedroom home, private HT, 2 living spaces, EV car charger
A residential area with houses, trees, and a clear sky.

17. 500 North Lupine Spacious & modern 3 bedroom, pet friendly in Fraser

500 North Lupine Spacious & modern 3 bedroom, pet friendly in Fraser
Fraser
9.8 out of 10, Exceptional, (38 reviews)
"Nice cabin for the holidays!"
United States
Nicole P.
The price is €588
includes taxes & fees
18 Oct - 19 Oct
500 North Lupine Spacious & modern 3 bedroom, pet friendly in Fraser
A modern kitchen with a large island, stainless steel appliances, and pendant lighting.

18. 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.
47 Lookout Point Rendezvous Spacious & Modern townhome sleeps 10 private hot tub
A living room with a fireplace, leather sofas, a TV, and a wooden entertainment unit.

19. Beautiful 3 Bedroom Townhome In Downtown Winter Park With Private Hot Tub

Beautiful 3 Bedroom Townhome In Downtown Winter Park With Private Hot Tub
Winter Park
9.8 out of 10, Exceptional, (62 reviews)
"Clean and responsive host. Would love to come back again!!"
United States
Ram
The price is €662
includes taxes & fees
18 Oct - 19 Oct
Beautiful 3 Bedroom Townhome In Downtown Winter Park With Private Hot Tub
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 €395
includes taxes & fees
18 Oct - 19 Oct
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 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 5 hours ago
The Trailhead | Beautifully Furnished Modern Condo In Downtown Winter Park

Find out more about Winter Park

Winter Park Holiday Homes information

Number of reviews
162
Accommodation
735 Holiday Homes
Lowest Price
€233
Highest Price
€662