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Our top choices for Winter Park vacation homes

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 ¥13,054
¥45,142 total
includes taxes & fees
Nov 6 - Nov 7
Hideaway Village Alpine 4 Split interior 2 bedroom, comfortable family rental

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 ¥11,096
¥42,831 total
includes taxes & fees
Nov 9 - Nov 10
Hideaway Village Lenado 4 Lovely townhome, river views, 2 private decks

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 ¥11,259
¥50,642 total
includes taxes & fees
Nov 14 - Nov 15
Timbers 5-2 Luxurious 2 bedroom, private deck, forest view

4. 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 ¥12,510
¥54,148 total
includes taxes & fees
Nov 6 - Nov 7
Timbers 9-4 New, spacious condo in Fraser, private deck and more!

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 ¥14,323
¥75,077 total
includes taxes & fees
Nov 6 - Nov 7
404 Doc Susie home Delightful and renovated home, walk to downtown, mt views

6. 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
The price is ¥20,451
¥71,487 total
includes taxes & fees
Nov 10 - Nov 11
Needles Eye 1 outstanding mt view private deck vaulted ceiling sleep 8

7. 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 ¥19,667
¥95,946 total
includes taxes & fees
Nov 10 - Nov 11
Fresh Tracks @ Peak View Ridge

8. 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 ¥21,539
¥72,005 total
includes taxes & fees
Nov 6 - Nov 7
534 Sun River #8 Wonderful Fraser 2 bedroom, pet friendly, large yard

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.
The price is ¥19,667
¥74,557 total
includes taxes & fees
Nov 10 - Nov 11
RidgeView Retreat | Steps to Hideaway Park & Town

10. 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 ¥27,015
¥103,143 total
includes taxes & fees
Nov 17 - Nov 18
Bear Crossing 995 Luxurious 3 bed, private hot tub, views, 1 car garage parking

11. 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 ¥18,763
¥65,688 total
includes taxes & fees
Nov 6 - Nov 7
Meadow Ridge Court 29 unit 8 Lovely and spacious 3 bedroom family condo rental

12. 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 ¥17,395
¥49,377 total
includes taxes & fees
Nov 9 - Nov 10
Close to slopes-Walk to Downtown Winter Park!

13. 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 ¥29,010
¥94,570 total
includes taxes & fees
Nov 6 - Nov 7
Red Quill 707 Luxury downtown, private HT, garage parking, walk to main st

14. 374 Lake Trail Luxury townhome, mt views, private decks and spacious floor plan

374 Lake Trail Luxury townhome, mt views, private decks and spacious floor plan
Winter Park
10.0 out of 10, Exceptional, (1 review)
"This was our first time in Winter Park. The location is great, being up the mountain a few minutes from the best shopping and restaurants. We saw moose 3x on the short drive! This condo is brand new, making it in great condition. It is very tastefully decorated and has plenty of great features. The double garage is tall enough to accomodate our SUV with yakima carrier. We had a few hiccups along the way with the unit being new, but they were all resolved very promptly. A few things to be...
United States
Ben G.
The price is ¥18,131
¥95,183 total
includes taxes & fees
Nov 9 - Nov 10
374 Lake Trail Luxury townhome, mt views, private decks and spacious floor plan

15. Bear Crossing 435 Luxurious 3 bedroom, mt views, garage parking & private decks

Bear Crossing 435 Luxurious 3 bedroom, mt views, garage parking & private decks
Winter Park
10.0 out of 10, Exceptional, (1 review)
"Everything about this place was perfection. The gorgeous views were the icing on the cake."
United States
Mandy G.
The price is ¥24,313
¥99,396 total
includes taxes & fees
Nov 6 - Nov 7
Bear Crossing 435 Luxurious 3 bedroom, mt views, garage parking & private decks

16. 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
9.4 out of 10, Exceptional, (3 reviews)
The price is ¥22,663
¥70,654 total
includes taxes & fees
Nov 6 - Nov 7
Waterside West B301 Large wrap around deck beautiful view of sunsets Byers Peak

17. 14 Explorer private townhome deck w/view garage

14 Explorer private townhome deck w/view garage
Rendezvous
The price is ¥31,331
¥114,142 total
includes taxes & fees
Nov 6 - Nov 7
14 Explorer private townhome deck w/view garage

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
The price is ¥24,476
¥131,053 total
includes taxes & fees
Nov 8 - Nov 9
Arrow At Winter Park Unit 294 Outdoor HT, private deck, downtown luxury townhome

19. 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.
The price is ¥21,849
¥57,508 total
includes taxes & fees
Nov 6 - Nov 7
Private Hot Tub, Garage + EV Charger, On Bus Line!

20. 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 ¥24,674
¥73,542 total
includes taxes & fees
Nov 9 - Nov 10
Hot tub, 3 bedroom, Ski friendly, New build, 5 star Luxury Retreat
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.

Learn more about Winter Park

Tucked between towering peaks, this mountain paradise offers world-class skiing and miles of uncrowded trails for summer hiking. Visit the charming downtown after a day outdoors, where local breweries serve perfect après-ski pints and restaurants welcome you in snow boots.

A snow-covered building with illuminated windows and a ski lift in the foreground.
Photo by Winter Park Resort
Open Photo by Winter Park Resort