Search Holiday Rentals in Winter Park

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Top Holiday Rentals in Winter Park

Zephyr Mountain Lodge
3.5 star property
8.2 out of 10, Very good, (619)
"The properly was clean and well kwpt however the beds were incredibly uncomfortable and very old. Honestly, this could’ve been a five star experience had the beds not been so incredibly uncomfortable for everyone in our party in three different rooms. We loved the walkability to the ski lift and the amenities and restaurants nearby. However, I would not stay here again because that’s how incredibly bad the beds were. Has five grown adults in their early 30s we all complained about the beds for a...
The price is €153
per night
2 Jun - 3 Jun
Zephyr Mountain Lodge
Indian Peaks Resort
3.5 star property
9.2 out of 10, Wonderful, (105)
"The private hot tub inside condo and views were the best!! I’ll stay here again!"
Indian Peaks Resort
Newly renovated Winter Park condo on the Fraser River
10.0 out of 10, Exceptional, (37)
"Everything was just as described in the web site ad. Very clean. The towels and washcloths were great quality (I even wrote down the brand name to purchase some). I had a question while we tee staying and the host was quick to reply to my email with an answer. Would highly recommend this place!"
Newly renovated Winter Park condo on the Fraser River
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**Downtown** Private Hot Tub, Garage, Fireplace & Washer/Dryer
10.0 out of 10, Exceptional, (340)
"We were in walking distance of most of the places we visited in Winter Park. The host was fantastic communicating with us. The condo was well equipped and very comfortable. We especially enjoyed being able to use the washer and drier. Thank you for a very nice place to stay in WP!"
The price is €225
per night
30 May - 31 May
**Downtown** Private Hot Tub, Garage, Fireplace & Washer/Dryer
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!
Zephyr Mountain Lodge/Slope Side Bldg True Ski/Bike in/ out with patio walk out
9.8 out of 10, Exceptional, (147)
"Nice comfy furniture & bed, well stocked kitchen, nice linens and bedding, great location!"
Zephyr Mountain Lodge/Slope Side Bldg True Ski/Bike in/ out with patio walk out
Luxe Downtown Winter Park Private Hot Tub 4 BR
9.8 out of 10, Exceptional, (46)
"This was the perfect location for our family Easter ski trip. Nice and close to the shuttle."
Luxe Downtown Winter Park Private Hot Tub 4 BR
Mountain view home with private hot tub, fireplace, WiFi, and washer/dryer
10.0 out of 10, Exceptional, (13)
"Lots of space for different couples; nicely stocked kitchen with all the pots, pans, and utensils needed; hot tub worked great, quiet, but parking very limited for a large group. Ski shuttle is not very close by - a solid ten minute walk down a hill (in ski boots with gear) and then up the hill after skiing - not ideal. We ended up driving to resort. Easy in and out - will book again in future."
Mountain view home with private hot tub, fireplace, WiFi, and washer/dryer
5br Luxury Mountain Home Sleeps 16: Hot Tub, Game Room, Free Ski/town Shuttle
10.0 out of 10, Exceptional, (208)
"Our family of 11 had a great stay for a family ski vacation. The owner is helpful and kind, besides being an excellent communicator. The house is wonderful. Its bedrooms are spacious, the beds comfortable, and each room quiet and private. The kitchen was well equipped to cook everything from pancakes to birthday cake to big dinners, and there was plenty of dishes, glasses, wine glasses, serving platters, etc. The large dining room table accommodated everyone easily, and the living room is set...
5br Luxury Mountain Home Sleeps 16: Hot Tub, Game Room, Free Ski/town Shuttle
Large 7 Bedroom Home, Mountain Setting, 3 family rooms, Hot Tub.
9.6 out of 10, Exceptional, (110)
"The house is big and comfy, plenty on beds and baths, but still very quiet once you are in the BRs. Gathering areas accommodate a large crowd. Kitchen is a bit dated but functional. Overall a great experience."
The price is €1,104
per night
1 Jun - 2 Jun
Large 7 Bedroom Home, Mountain Setting, 3 family rooms, Hot Tub.
Gorgeous home just across from Winter Park Resort with BREATHTAKING view!
9.4 out of 10, Exceptional, (24)
"Amazing view great amenities"
Gorgeous home just across from Winter Park Resort with BREATHTAKING view!
Amazing Cabin Just Above Downtown Winter Park. Private Hot Tub!
10.0 out of 10, Exceptional, (23)
"The house was as advertised. Clean, close to town, shuttle and resort. Views off the back deck were amazing."
Amazing Cabin Just Above Downtown Winter Park. Private Hot Tub!
Spacious ski condo with fireplace, pool, hot tub & free shuttle to Winter Park
8.2 out of 10, Very good, (12)
"Great location and super cozy. Loved the layout and individual thermostats. Well appointed kitchen and bar!"
Spacious ski condo with fireplace, pool, hot tub & free shuttle to Winter Park
The Trailhead | Beautifully Furnished Modern Condo In Downtown Winter Park
10.0 out of 10, Exceptional, (168)
"Everything was great and as advertised."
The price is €426
per night
18 Jun - 19 Jun
The Trailhead | Beautifully Furnished Modern Condo In Downtown Winter Park
A Frame Club
3.0 star property
9.4 out of 10, Exceptional, (69)
"Great place. Close to the mountain. Good food. Very accommodating "
A Frame Club
Luxurious home 9 Bedrooms, 6 bath, hot tub, resort views!
9.6 out of 10, Exceptional, (55)
"This house was everything we wanted and more! So much room to spread out, plenty of beds for everyone and the house came with everything we needed. The kitchen is fully stocked with every pan and dish you could need. We cooked a lot of our meals at the house and loved having everything by we needed. The stove was a little tricky to get lit, but once we figured out that you have to slowly turn the dial after it is lit, it was no problem. All of the beds were very comfortable as well. Everyone...
The price is €2,285
per night
29 Jun - 30 Jun
Luxurious home 9 Bedrooms, 6 bath, hot tub, resort views!
Renovated Condo near the Slopes and Trails
9.4 out of 10, Exceptional, (144)
"Very nice and comfortable Pet Friendly stay at a fair price with great hot tub and pool!!"
The price is €366
per night
3 Jun - 4 Jun
Renovated Condo near the Slopes and Trails
Large Glass Front with Beautiful Mountain Views
9.8 out of 10, Exceptional, (140)
"Our stay was fabulous. It was easy to get to town and the shuttle and the space was comfortable for our family. It would be helpful to know about the loft style and lack of door in bedrooms for noise planning for the little one ahead of time."
Large Glass Front with Beautiful Mountain Views
Dog-Friendly Winter Park Townhome w/ Mtn Views!
8.8 out of 10, Excellent, (8)
"We were really happy with our stay here! The bus stop is steps away from the end of the driveway which is amazing. The garage has stairs that you can access the property which is nice. There is also a table in the garage that we used to sit and get our ski gear on. It was handy to be able to leave all our gear down there. The yard was covered with five feet of snow, so my dogs walked right over the fence. Lol. We had to be creative... My son built a snow fence and we just used the back deck for...
Dog-Friendly Winter Park Townhome w/ Mtn Views!
Silverado II Resort & Event Center
3.5 star property
8.2 out of 10, Very good, (143)
"It was just what we needed for a long weekend ski trip of 4 days. The Winter Park ski shuttle picks you up right in front of the hotel by the road. It’s a little difficult to walk in the snow to the main road, so make friends with or find out the number to the local shuttle driver in the evenings who can get you to one of the couple of restaurants or a grocery store. Full kitchen was great. Fireplace was also nice. Very spacious 2 bedroom unit with plenty of living room space, dining table and...
Silverado II Resort & Event Center
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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.

Other types of properties in Winter Park you may be interested in

Gravity Haus Winter Park
3.5 star property
9.0 out of 10, Wonderful, (445)
"Enjoyed our stay. Hot tubs were amazing and room was clean and comfortable, however it could use some attention to paint there was several scratches and dents in wood that brought down the feel of such a clean room. "
The price is €122
per night
3 Jun - 4 Jun
Gravity Haus Winter Park
The Vintage Hotel
3.0 star property
8.6 out of 10, Excellent, (1005)
"Everything was beyond expectations! "
The price is €98
per night
2 Jun - 3 Jun
The Vintage Hotel
Winter Park Mountain Lodge
3.0 star property
7.0 out of 10, Good, (1001)
"super convenient to winter park ski base with free public shuttle that runs all day. restraunt service at the hotel is convenient when its open. not tubs have a great view, but could be cleaner. "
The price is €99
per night
9 Jun - 10 Jun
Winter Park Mountain Lodge
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.

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.

How many holiday rentals are there in Winter Park?

With 526 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.

Recent reviews of Winter Park properties
Expedia verified reviews