Holiday Homes in Winter Park

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Featured Holiday Homes in Winter Park and around

Spacious & Luxurious 8-Bedroom Retreat in Downtown Winter Park on Vasquez Creek

9.8 out of 10, Exceptional, (133)
"Awesome as always, we love staying here for our company ski weekend !!!"
Spacious & Luxurious 8-Bedroom Retreat in Downtown Winter Park on Vasquez Creek

Luxurious Home,1 acre,6mile-W.Park,Hot tub,33miles-RMNP, 2 Masters, Steam Shower

10.0 out of 10, Exceptional, (169)
"Absolutely perfect! The host was fast with replies, very well furnished house including reading glasses, views were amazing, and this spacious house beyond any of our expectations!! We will definitely book again!"
The price is €457
includes taxes & fees
13 Oct - 14 Oct
Luxurious Home,1 acre,6mile-W.Park,Hot tub,33miles-RMNP, 2 Masters, Steam Shower

4BR Mountain Escape Family Friendly, Sleeps 10

2.0 star property
9.6 out of 10, Exceptional, (9)
"Great trip. Snow was perfect"
The price is €555
includes taxes & fees
2 Oct - 3 Oct
4BR Mountain Escape Family Friendly, Sleeps 10

Winter Park Luxury Home

Winter Park Luxury Home

Luxury Downtown Condo - Private Hot Tub! Walk to Dining and Ski Bus...

10.0 out of 10, Exceptional, (73)
"We stayed here for a family wedding. Great accommodations and Bob was great to work with!"
Luxury Downtown Condo - Private Hot Tub! Walk to Dining and Ski Bus...

Split interior 2 bedroom, comfortable family rental

9.0 out of 10, Wonderful, (4)
"It was a good location. It was nice and clean. "
The price is €246
includes taxes & fees
7 Oct - 8 Oct
Split interior 2 bedroom, comfortable family rental

Trailhead 524 Clubhouse w/ Hot tub | Pool

9.8 out of 10, Exceptional, (46)
"Comfortable and good location."
Trailhead 524 Clubhouse w/ Hot tub | Pool

Large Home, 11 beds, 2 Family Rooms, Hot Tub!

9.6 out of 10, Exceptional, (9)
"Nice house to stay during weekend with family"
The price is €925
includes taxes & fees
29 Sept - 30 Sept
Large Home, 11 beds, 2 Family Rooms, Hot Tub!

2 Masters, Private Hot Tub, Superb Views - Close to WP Resort Skiing, Biking

9.8 out of 10, Exceptional, (68)
"This is our second time staying here, we’ll be back next year! "
2 Masters, Private Hot Tub, Superb Views - Close to WP Resort Skiing, Biking

Slopeside River Front Luxury Chalet I HotTub I Firepit I Views I Best Price I Discounted Attractions

9.6 out of 10, Exceptional, (77)
"Skied a few sunny days and enjoyed the location quite a bit. Helpful host services and comfortable house. "
Slopeside River Front Luxury Chalet I HotTub I Firepit I Views I Best Price I Discounted Attractions

Spacious Townhome with Private Hot Tub, minutes away from Winter Park Resort

9.6 out of 10, Exceptional, (55)
"Incredible stay and super clean!"
Spacious Townhome with Private Hot Tub, minutes away from Winter Park Resort

Townhouse near Winter Park w/ hot tub

9.8 out of 10, Exceptional, (43)
"Great condo, much more spacious than it appears and great location. Loved our stay!"
Townhouse near Winter Park w/ hot tub

🐻 Bear Crossing 1390 | Pet Friendly For One Dog | Private Hot Tub

9.8 out of 10, Exceptional, (56)
"We enjoyed our stay. The condo was comfortable and very well located. Would certainly stay there again."
🐻 Bear Crossing 1390 | Pet Friendly For One Dog | Private Hot Tub

Luxury Ski in/Ski out town home, private hot tub, great for families and groups

10.0 out of 10, Exceptional, (32)
"Loved it"
Luxury Ski in/Ski out town home, private hot tub, great for families and groups

Custom Timber Home-Great Rates,Central Loc,Views,2 Living Spaces,On Free Shuttle

9.6 out of 10, Exceptional, (122)
"This was our 2nd year to stay here for our annual family ski trip. Very spacious home and convenient location."
Custom Timber Home-Great Rates,Central Loc,Views,2 Living Spaces,On Free Shuttle

3BR townhouse w/ balcony & hot tub

10.0 out of 10, Exceptional, (3)
"Wonderful property! 5 star and would stay here again. "
3BR townhouse w/ balcony & hot tub

'Snow Dream'- the Ultimate Family Retreat

9.8 out of 10, Exceptional, (155)
"Great place to stay for a full group! The hot tub was wonderful and the kitchen was well stocked. Wish we would have stayed longer!"
'Snow Dream'- the Ultimate Family Retreat

Winter Park Retreat - In The Heart Of Downtown

9.8 out of 10, Exceptional, (63)
"Location was great! Host was very responsive. House was perfect size for our family. Would definitely stay again! "
Winter Park Retreat - In The Heart Of Downtown

3 BR with Private Hot Tub and views of the slopes in prestigious Lakota!!

10.0 out of 10, Exceptional, (99)
"We really enjoyed this place! It was clean and easy access to and from WP mountain. "
3 BR with Private Hot Tub and views of the slopes in prestigious Lakota!!

Moose Lodge with private hot tub

10.0 out of 10, Exceptional, (6)
"This house was perfect for an extended family gathering for ski weekend at Winter Park. Great location, and good amenities for cooking in which we like to do. "
Moose Lodge with private hot tub
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

Find out more about Winter Park

Winter Park Holiday Homes information

Number of reviews
1,022
Accommodation
714 Holiday Homes
Lowest Price
€246
Highest Price
€925

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