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Our top choices for Winter Park holiday homes

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 £249
includes taxes & fees
13 Nov - 14 Nov
Timbers 5-2 Luxurious 2 bedroom, private deck, forest view

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, (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 £217
includes taxes & fees
9 Nov - 10 Nov
Hideaway Village Alpine 4 Split interior 2 bedroom, comfortable family rental

3. 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 £204
includes taxes & fees
18 Nov - 19 Nov
Hideaway Village Lenado 4 Lovely townhome, river views, 2 private decks

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 £257
includes taxes & fees
9 Nov - 10 Nov
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 £359
includes taxes & fees
9 Nov - 10 Nov
404 Doc Susie home Delightful and renovated home, walk to downtown, mt views

6. 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 £512
includes taxes & fees
22 Nov - 23 Nov
Fresh Tracks @ Peak View Ridge

7. 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.
Close to slopes-Walk to Downtown Winter Park!

8. 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 £336
includes taxes & fees
9 Nov - 10 Nov
RidgeView Retreat | Steps to Hideaway Park & Town

9. 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 £342
includes taxes & fees
10 Nov - 11 Nov
Needles Eye 1 outstanding mt view private deck vaulted ceiling sleep 8

10. 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 £445
includes taxes & fees
9 Nov - 10 Nov
374 Lake Trail Luxury townhome, mt views, private decks and spacious floor plan

11. 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 £341
includes taxes & fees
9 Nov - 10 Nov
Hot tub, 3 bedroom, Ski friendly, New build, 5 star Luxury Retreat

12. 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 £493
includes taxes & fees
9 Nov - 10 Nov
Bear Crossing 995 Luxurious 3 bed, private hot tub, views, 1 car garage parking

13. 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 £333
includes taxes & fees
9 Nov - 10 Nov
534 Sun River #8 Wonderful Fraser 2 bedroom, pet friendly, large yard

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 £356
includes taxes & fees
9 Nov - 10 Nov
The AlpenGlow House: Private Hot Tub Retreat with Stunning Mountain Views!

15. 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 £617
includes taxes & fees
9 Nov - 10 Nov
Arrow At Winter Park Unit 294 Outdoor HT, private deck, downtown luxury townhome

16. 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 £271
includes taxes & fees
9 Nov - 10 Nov
Private Hot Tub, Garage + EV Charger, On Bus Line!

17. 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 £314
includes taxes & fees
9 Nov - 10 Nov
Meadow Ridge Court 29 unit 8 Lovely and spacious 3 bedroom family condo rental

18. 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 £475
includes taxes & fees
9 Nov - 10 Nov
Bear Crossing 435 Luxurious 3 bedroom, mt views, garage parking & private decks

19. 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.
Mountain escape, minutes from Winter Park resort and town. Hot tub access.

20. Family Condo near WP | Bike, Hike, Pool & Hot Tubs

Family Condo near WP | Bike, Hike, Pool & Hot Tubs
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.
Family Condo near WP | Bike, Hike, Pool & Hot Tubs
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

Find out more about Winter Park

Winter Park Holiday Homes information

Number of reviews
67
Accommodation
735 Holiday Homes
Lowest Price
£204
Highest Price
£617