Holiday houses in Winter Park

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Popular amenities for Winter Park holiday rentals

Other great holiday rentals in Winter Park

Superhost
Home in Winter Park
5 out of 5 average rating, 3 reviews

Luxury Mountain Modern Winter Park Home

GaryRating, 5 stars4 days ago
This place was incredible! Peaceful and pretty secluded, but close enough to town to bike or take a little walk. The home was immaculate and stocked with anything we may need. Views were amazing from the windows and especially the deck. Owners were super friendly and easy to work with.
Top Guest favourite
Condo in Fraser
5 out of 5 average rating, 60 reviews

NEW-Private HOT TUB-Garage-Coffee bar-Boot Dryer

MaggieRating, 5 stars1 week ago
Kelly’s place was absolutely perfect. Everything we needed was there for us to use. It was spotless, smelled nice, great location and private! The hot tub was such a bonus it was great. There were also chairs and a cooler in the garage for us to use when we took a day trip to the National Park. Look forward to staying there again!
Guest favourite
Apartment in Winter Park
5 out of 5 average rating, 10 reviews

Cozy Winter Park Condo - Heart of Town

WillRating, 5 stars2 months ago
We had a great stay at David’s condo. You can’t beat the location. Walking distance to all the restaurants and a 1 minute walk to the free bus to take you to winter park as the next stop. It took us a little bit to find a way into the building but entering from the parking garage was easy and didn’t require another key as some of the outer doors on other floors do.
Guest favourite
Guest suite in Fraser
4.93 out of 5 average rating, 89 reviews

A+ Cozy, Stylish Studio Nestled in Old Town Fraser

LeighRating, 5 stars2 months ago
Elizabeth's place was extremely clean and well stocked with everything you need for your stay. Perfect spot for a Spring ski weekend!
Guest favourite
Home in Winter Park
5 out of 5 average rating, 11 reviews

New Luxury Condo 2203 I Free Adventures Daily

Nancy and NedRating, 5 stars3 months ago
My son and I booked the condo for a late planned ski trip. The condo is very comfortable, clean and modern. It has an adequately stocked kitchen with plenty of utensils and spices for those that prefer to cook. It includes a drip coffee maker and a separate bean grinder (I never know what to buy before arriving). There is some ongoing new construction in the area (as of March 2025). I heard some trucks backing up in the morning, but it did not bother us as we were up each morning to ski. Overall, the place is very quiet with very minimal neighbor noise. There is no cable service, so be prepared to stream or cast from your own device using your own accounts. I was able to stream YouTube TV from my phone to the TV. We took the free shuttle service to the resort each day. It’s a quick walk to the bus stop, and we never waited more than a few minutes for a bus. We walked to the area restaurants and shops. Safeway is a quick drive down the street. We would book again.
Guest favourite
Condo in Winter Park
4.95 out of 5 average rating, 40 reviews

Hi Country Hideaway

AdriaRating, 5 stars2 months ago
Perfect place for our ski trip! Walkable and beautiful location with easy access to free shuttle to the resort. Kelly was friendly and provided great information. Would recommend!
Top Guest favourite
Home in Winter Park
5 out of 5 average rating, 71 reviews

Cozy Modern Cabin w/ Hot Tub - Minutes to Ski Area

DarinRating, 5 stars1 month ago
We loved our stay! Kristen was a great host, very helpful and responsive. Really appreciated how clean and comfortable the place was!
Guest favourite
Chalet in Winter Park
5 out of 5 average rating, 10 reviews

Charming 4BR Chalet with Hot Tub & Mountain Views

KimRating, 5 stars3 weeks ago
This property was exceptional. I cannot say enough about how high end and comfortable it was. It includes all the amenities one would want for a family. Close proximity to trails, dining, retail and the beauty was unmatched. highly recommend. awesome boat as well

Quick stats about holiday rentals in Winter Park

  • Total rentals

    1.5K properties

  • Nightly prices starting at

    $17 NZD before taxes and fees

  • Total number of reviews

    44K reviews

  • Family-friendly rentals

    1.2K properties are a good fit for families

  • Pet-friendly rentals

    250 properties allow pets

  • Rentals with a pool

    620 properties have a pool

Destinations to explore

  1. Airbnb
  2. United States
  3. Colorado
  4. Grand County
  5. Winter Park