Holiday Homes in Winter Park

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Check prices for these dates

Next weekend
22 Aug - 24 Aug
In two weeks
29 Aug - 31 Aug
In one month
12 Sept - 14 Sept
In two months
10 Oct - 12 Oct

Featured Holiday Homes in Winter Park

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

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

10.0 out of 10, Exceptional, (165)
"I was very nice place and we would recommend it"
Luxurious Home,1 acre,6mile-W.Park,Hot tub,33miles-RMNP, 2 Masters, Steam Shower
💎 Deluxe Hot Tub W/ Stunning Views | Custom Decor | Across From Ski Resort
Outdoor dining

💎 Deluxe Hot Tub W/ Stunning Views | Custom Decor | Across From Ski Resort

10.0 out of 10, Exceptional, (32)
"The location, the house, and the communication were all exceptional and made the entire process not just easy but enjoyable. Thank you all for your help!"
💎 Deluxe Hot Tub W/ Stunning Views | Custom Decor | Across From Ski Resort
AMAZING Mtn Views, Private Hot Tub, Fireplace, next to River Trail !!
Fridge, microwave, oven, stovetop

AMAZING Mtn Views, Private Hot Tub, Fireplace, next to River Trail !!

10.0 out of 10, Exceptional, (191)
"Great spot for skiing WP. Hot tub is always amazing after a long day. Shannon’s baked treats are incredible. Can’t go wrong with this place!"
AMAZING Mtn Views, Private Hot Tub, Fireplace, next to River Trail !!
Winter Park Retreat - In The Heart Of Downtown
TV, fireplace, DVD player, video library

Winter Park Retreat - In The Heart Of Downtown

9.8 out of 10, Exceptional, (61)
"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
Stunning townhome. Few minutes from Winter Park Ski Resort and Town of WP
Fridge, microwave, oven, stovetop

Stunning townhome. Few minutes from Winter Park Ski Resort and Town of WP

9.6 out of 10, Exceptional, (94)
"Amazing place to stay and close to the winter pak"
Stunning townhome. Few minutes from Winter Park Ski Resort and Town of WP
Luxury Mountain Cabin 27 I Great Views I Best Price I Discounted Attractions
Outdoor dining

Luxury Mountain Cabin 27 I Great Views I Best Price I Discounted Attractions

10.0 out of 10, Exceptional, (13)
"We can't say enough about our stay! The place was super clean and supplied with everything we couldn't wanted, from the kitchen and pantry items to the games and puzzles. The river is beautiful flowing through the campus. We loved staying there and can't wait to return."
Luxury Mountain Cabin 27 I Great Views I Best Price I Discounted Attractions
🐻 Bear Crossing 1390 | Pet Friendly For One Dog | Private Hot Tub
Exterior

🐻 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
New Listing! 3 Miles to Resort | Hot Tub | Fireplace | EV Charger
Fridge, microwave, oven, stovetop

New Listing! 3 Miles to Resort | Hot Tub | Fireplace | EV Charger

10.0 out of 10, Exceptional, (2)
"We enjoyed our stay! Very nice and clean home with a great location."
The price is NZ$1,285
includes taxes & fees
26 Aug - 27 Aug
New Listing! 3 Miles to Resort | Hot Tub | Fireplace | EV Charger
Best Value Luxury Townhome in Lakota across from Ski Resort, Private Hot Tub!
Outdoor dining

Best Value Luxury Townhome in Lakota across from Ski Resort, Private Hot Tub!

10.0 out of 10, Exceptional, (92)
"Great property 15 minute walk to the slopes. Decorated for Christmas, a nice touch!Only complaint is bunk beds are a little short for full size male adults."
Best Value Luxury Townhome in Lakota across from Ski Resort, Private Hot Tub!
Eagle Wind Lodge | Large & Luxe Ski Lodge | Private Hot Tub | Movie & Game Room
Exterior detail

Eagle Wind Lodge | Large & Luxe Ski Lodge | Private Hot Tub | Movie & Game Room

10.0 out of 10, Exceptional, (70)
"We all had an amazing time!"
Eagle Wind Lodge | Large & Luxe Ski Lodge | Private Hot Tub | Movie & Game Room
Perfect mountain getaway any time of year!
Exterior

Perfect mountain getaway any time of year!

9.4 out of 10, Exceptional, (64)
"Property was in great shape. Very roomy and comfortable. Highly recommend."
Perfect mountain getaway any time of year!
New Listing! Hot Tub & Fireplace Mountain Retreat
Outdoor dining

New Listing! Hot Tub & Fireplace Mountain Retreat

10.0 out of 10, Exceptional, (2)
"Really nice place "
New Listing! Hot Tub & Fireplace Mountain Retreat
Luxury Ski in/Ski out town home, private hot tub, great for families and groups
Smart TV, fireplace

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
Slopeside Custom Chalet I 2 Hot Tubs I Fire Tables I Views I Best Price I Discounted Attractions
Fridge, microwave, oven, stovetop

Slopeside Custom Chalet I 2 Hot Tubs I Fire Tables I Views I Best Price I Discounted Attractions

10.0 out of 10, Exceptional, (2)
"We really enjoyed our stay. The property is beautiful and the location is perfect. We would love to come back and stay again. Thank you! "
Slopeside Custom Chalet I 2 Hot Tubs I Fire Tables I Views I Best Price I Discounted Attractions
Spacious home w/ kitchen, wifi, great views, deck & convenient location
Fridge, microwave, oven, stovetop

Spacious home w/ kitchen, wifi, great views, deck & convenient location

9.6 out of 10, Exceptional, (34)
"Great location and property had everything we needed "
Spacious home w/ kitchen, wifi, great views, deck & convenient location
Wonderful Fraser 2 bedroom, pet friendly, large yard
Fridge, microwave, oven, stovetop

Wonderful Fraser 2 bedroom, pet friendly, large yard

8.0 out of 10, Very good, (4)
"I really like this property. The location in Fraser is walking distance to some fun spots, and quick drive to both Winter Park and Mary Jane. It's spacious and clean and we fit four adults very comfortably."
The price is NZ$744
includes taxes & fees
13 Sept - 14 Sept
Wonderful Fraser 2 bedroom, pet friendly, large yard
☼ Ski Resort Views From Deck | Slopeside 202 | Private Hot Tub
Exterior

☼ Ski Resort Views From Deck | Slopeside 202 | Private Hot Tub

10.0 out of 10, Exceptional, (42)
"This property has all the amenities, comfortable beds and a great location."
☼ Ski Resort Views From Deck | Slopeside 202 | Private Hot Tub
Beautiful home in Fraser with great breathtaking views and private hot tub
TV

Beautiful home in Fraser with great breathtaking views and private hot tub

9.6 out of 10, Exceptional, (87)
"This cabin was exactly what we were looking for. We had a wonderful weekend away."
Beautiful home in Fraser with great breathtaking views and private hot tub
Rustic meets contemporary in this gorgeous Townhome w/ private hot tub
Fridge, microwave, oven, stovetop

Rustic meets contemporary in this gorgeous Townhome w/ private hot tub

9.8 out of 10, Exceptional, (49)
"This VRBO was all around very pleasant. Everything was clean and things like the grill and hot tub worked very well when I can’t say the same for other places I’ve visited. The host was responsive and I’d recommend this stay"
Rustic meets contemporary in this gorgeous Townhome w/ private hot tub
Spacious 6BR Mountain Getaway! On Shuttle Route, Hot Tub, Game Room, Sleeps 16+
Exterior

Spacious 6BR Mountain Getaway! On Shuttle Route, Hot Tub, Game Room, Sleeps 16+

9.8 out of 10, Exceptional, (119)
"Exactly as advertised and worked perfectly for our two families. Would definitely stay here again"
Spacious 6BR Mountain Getaway! On Shuttle Route, Hot Tub, Game Room, Sleeps 16+
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

Gravity Haus Winter Park

Gravity Haus Winter Park

10/10 Excellent
"Fun lobby for hanging out. Great cocktails and excellent coffee. Great outdoor patio for hanging out and right in the heart of downtown Winter Park. "
Amy 1-night trip
Posted 2 days ago
Gravity Haus Winter Park