Winter Park Holiday Rentals

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Holiday Rentals in Winter Park

Zephyr Mountain Lodge
3.5 star property
8.2 out of 10, Very good, (635)
" Great room, very roomie can easily sleep four ppl. Staff was great, helped whenever we needed. Just know that on building one and two the wifi does not work on the smart tv because you can’t sign in with room number. Room was clean smelled Great plenty of space and it’s a Mountain View "
The price is AU$530
includes taxes & fees
2 Dec - 3 Dec
Zephyr Mountain Lodge
A Frame Club
3.5 star property
9.2 out of 10, Wonderful, (75)
"My husband and I stayed here for a night and it was a wonderful and quaint getaway from the hectic life. We have already recommended A-Frame Club to friends and family"
The price is AU$563
includes taxes & fees
24 Nov - 25 Nov
A Frame Club
Indian Peaks Resort
3.5 star property
9.2 out of 10, Wonderful, (114)
"Sin duda regresaré nos encanto Ami y a mi familia "
Indian Peaks Resort
Silverado II Resort & Event Center
3.5 star property
8.2 out of 10, Very good, (145)
"The Staff at Silverado II were so friendly and helpful. The rooms are exceptional and comfortable. I would reccomend this place to anyone planning a stay in Winter Park."
Silverado II Resort & Event Center
**Downtown** Private Hot Tub, Garage, Fireplace & Washer/Dryer
10.0 out of 10, Exceptional, (352)
"Check-in process was easy. Communication with the property managers was fast and accurate. Was they able to check in before the check in time that was very nice the property managers. The condo was nice and clean. Had everything you would need for weekend or week trip. went to Park jazz festival, had a great time. I will be looking to stay at this condo in 2025 for the winter jazz festival. Having a hot tub on your patio added the icing to the cake. Very close to downtown you could even walk if...
**Downtown** Private Hot Tub, Garage, Fireplace & Washer/Dryer
5br Luxury Mountain Home Sleeps 16: Hot Tub, Game Room, Free Ski/town Shuttle
10.0 out of 10, Exceptional, (215)
"Very comfortable and clean house. Many nice touches and amenities. Very nice hot tub and beds. "
5br Luxury Mountain Home Sleeps 16: Hot Tub, Game Room, Free Ski/town Shuttle
The Trailhead | Beautifully Furnished Modern Condo In Downtown Winter Park
10.0 out of 10, Exceptional, (186)
"Great location right in town. Walk to many restaurants and stores. Easy drive to several trail heads. Great place"
The Trailhead | Beautifully Furnished Modern Condo In Downtown Winter Park
Trestle House | Ski Out Your Back Door | WP's Most Stunning Home INSTAGRAM FAMOUS!
10.0 out of 10, Exceptional, (11)
"This home has it all. We absolutely loved staying at Trestle house and we hope to come back again soon. The game room was a huge hit for sure and the spacious living/kitchen/dinning area was amazing, My favorite part was watching the snow cats go by the house every morning while drinking our coffee ❤️"
Trestle House | Ski Out Your Back Door | WP's Most Stunning Home INSTAGRAM FAMOUS!
Amazing Cabin Just Above Downtown Winter Park. Private Hot Tub!
10.0 out of 10, Exceptional, (25)
"We loved this cozy, clean and character-filled cabin! The deck and hot tub set up and views were awesome! Highly recommend…."
Amazing Cabin Just Above Downtown Winter Park. Private Hot Tub!
Lux 8000 SQ Ft, 9 BDR, 15 Beds, Hot Tub, Large Groups!
9.6 out of 10, Exceptional, (59)
"Beautiful home, very nice furniture, kitchen was well stocked with dishes, etc. Clean. Yard is well landscaped and maintained. Staff had a great time and enjoyed their meeting. We will rent this property again in the future."
Lux 8000 SQ Ft, 9 BDR, 15 Beds, Hot Tub, Large Groups!
Large Glass Front with Beautiful Mountain Views
9.8 out of 10, Exceptional, (141)
"It was all we could ask for! Quiet, clean and great WiFi! This spot had everything we needed. Close to town, nicely equipped kitchen and all the night sky you could ask for!"
Large Glass Front with Beautiful Mountain Views
Mountain view home with private hot tub, fireplace, WiFi, and washer/dryer
9.8 out of 10, Exceptional, (16)
"Time to relax in the mountains"
Mountain view home with private hot tub, fireplace, WiFi, and washer/dryer
Luxe Downtown Winter Park Private Hot Tub 4 BR
9.8 out of 10, Exceptional, (57)
"We had a party of 10 with 4 adults a 16 year old, 2 13 year olds, 2 9 year olds, and a 7 year old with plenty of space for all to be comfortable. The home was perfectally located right by Hideaway Park to make everything accessible for walking and biking, with all the trails we love close by. Barely drove the car and biked everywhere. The place was super clean and worked perfect for our larger group."
Luxe Downtown Winter Park Private Hot Tub 4 BR
Luxury Condo with Hot Tub, Pool, & Private Patio in the Heart of Winter Park!
10.0 out of 10, Exceptional, (21)
"We had a great experience and would happily book again"
Luxury Condo with Hot Tub, Pool, & Private Patio in the Heart of Winter Park!
Renovated Condo near the Slopes and Trails
9.4 out of 10, Exceptional, (149)
"We stayed in this condo for a summer trip. The location was perfect for our needs. One of our favorite restaurants was within walking distance. The condo was clean, very comfortable and was stocked with everything we needed. I would definitely stay here again. "
The price is AU$656
includes taxes & fees
30 Nov - 1 Dec
Renovated Condo near the Slopes and Trails
Tree-Lined Townhome Downtown w/Private Hot Tub, Slope Views, Fireplace, WiFi
9.4 out of 10, Exceptional, (34)
"We had such a great family stay in this condo unit! It had all we needed with the exception of sharp knives which is a small thing! Thanks for letting us enjoy your space!"
Tree-Lined Townhome Downtown w/Private Hot Tub, Slope Views, Fireplace, WiFi
Condo w/ View - 1 Block to Main St - 4 Mi to Ski!
10.0 out of 10, Exceptional, (56)
"My daughter and I were heading to Colorado to see a concert at Red Rocks. I couldn't find a place close to the amphitheater that we were interested in staying, so we decided to head up into the mountains. We definitely made the right decision. This condo in Winter Park was nothing short of fabulous! It is perfectly decorated and stocked with everything that you will need. The beds are super comfortable and the large TVs are nice. The bathroom spaces are amazing! The condo is in walking distance...
Condo w/ View - 1 Block to Main St - 4 Mi to Ski!
9 BDR Home downtown Winter Park, Hot Tub, Shuttle, Sleeps 19!
9.4 out of 10, Exceptional, (44)
"The layout and location of this home were perfect! We were a family with adult couples looking for enough bedrooms and space to spend the weekend together. This worked perfectly. The floor plan of this home is ideal for that, the kitchen was well equipped and the living spaces were great. The home definitely shows signs of wear and could use some love but we will definitely consider a re book for next year."
The price is AU$2,579
includes taxes & fees
16 Dec - 17 Dec
9 BDR Home downtown Winter Park, Hot Tub, Shuttle, Sleeps 19!
Fully Remodeled, Two Bed, Two Bath, Best Views, Steps from Town
9.8 out of 10, Exceptional, (48)
"We had a great stay here right before the spring break rush. Gorgeous views! Beds were very comfortable and there was plenty of space for our family of 5. Coming from the plains of the Midwest, the walk and stairs were a struggle with the elevation but it was worth it with the view from the balcony. We had one minor issue with bedding but the hosts were very quick to reply and handle it for us!"
Fully Remodeled, Two Bed, Two Bath, Best Views, Steps from Town
Beautiful Cozy Studio at the Base With Heated Parking
9.8 out of 10, Exceptional, (66)
"I loved this unit! Parking was easy and the unit was well-appointed with all your needs for a comfortable stay. I especially appreciated the big bathtub after miles of hiking in beautiful Winter park. "
Beautiful Cozy Studio at the Base With Heated Parking
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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Other types of properties in Winter Park you may be interested in

Winter Park Mountain Lodge
3.0 star property
6.8 out of 10, (1001)
"Very nice place and all the staff was very nice. Love it!"
The price is AU$241
includes taxes & fees
24 Nov - 25 Nov
Winter Park Mountain Lodge
Gravity Haus Winter Park
3.5 star property
9.0 out of 10, Wonderful, (563)
"I love staying at Gravity Haus, it’s a cheap, it’s clean, and everything is super convenient."
The price is AU$180
includes taxes & fees
24 Nov - 25 Nov
Gravity Haus Winter Park
The Vintage Hotel
3.0 star property
8.6 out of 10, Excellent, (1000)
"Cool ski town hotel convenient and simple. "
The price is AU$356
includes taxes & fees
2 Dec - 3 Dec
The Vintage Hotel
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.
Beautiful view of the beach with palm trees

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Frequently asked questions

Can I find holiday rentals in Winter Park?

Yes, there are holiday rentals in Winter Park close to Amaze'n Maze Winter Park, or you can select a more secluded option if you're looking for a relaxing stay. Visitors like the ski slopes and majestic mountain landscape in Winter Park. You can also check out the live music while you're visiting.

What are some of the best holiday rentals that Winter Park has to offer?

Luxe Downtown Winter Park Private Hot Tub 4 BR: This highly rated holiday home rental in Winter Park is located on a river, and has a fireplace, a balcony and laundry facilities to put you at ease in your new surroundings. It has 5 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a selection of games and 1 hot tub. Other favourite homes for rent in Winter Park are Tree-Lined Townhome Downtown w/Private Hot Tub, Slope Views, Fireplace, WiFi and 5br Luxury Mountain Home Sleeps 16: Hot Tub, Game Room, Free Ski/town Shuttle.

How many holiday rentals are there in Winter Park?

With 518 Expedia holiday rentals, you're guaranteed to find just the right place for your Winter Park stay.

What’s there to see and do in Winter Park?

The Fraser River Trail and Arapaho National Recreation Area are a couple of lovely local spots to enjoy the outdoors, whereas family-friendly attractions include Amaze'n Maze Winter Park. While here, Winter Park Ski Resort and Trestle Bike Park are other places worth a visit.

What’s a holiday rental in Winter Park like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Winter Park. Holiday rentals provide amenities such as patios, hot tubs and fire pits so you'll have everything you want. If you're concerned about cleanliness, a holiday rental can offer a sense of safety away from shared hotel lifts and busy lobbies while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a standard hotel, which makes a holiday rental a great option for family trips or small group gatherings.