Holiday houses in Winter Park

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Top-rated holiday rentals in Winter Park

Guests agree: these stays are highly rated for location, cleanliness and more.

Guest favourite

Cabin in Winter Park

4.94 out of 5 average rating, 197 reviews

Cozy Log Home,Sleeps 10. Free shuttle,3 min-slopes

MikeRating, 5 starstoday
A Cozy Mountain Retreat! Our stay at this mountain cabin was nothing short of magical. The cabin itself was perfect — rustic yet modern, with stunning views of the surrounding mountains. The space was clean, well-maintained, and had all the amenities you could need! The location is extremely ideal for anyone looking to enjoy nature. Winter Park ski resort is extremely close. The cabin also had a wonderful deck where we spent hours relaxing with a cup of coffee and taking in the breathtaking views. What really made our experience unforgettable, though, was Sherri. She went above and beyond in every way! From the seamless check-in process to the personalized recommendations for local restaurants and activities, it was clear that she truly cares about her guests. She was always quick to respond to any questions, and her friendly, welcoming nature made us feel right at home. It’s rare to find a host so dedicated to making sure your stay is perfect!
Superhost

Condo in Granby

4.89 out of 5 average rating, 103 reviews

Mountain Loft-Views-Pool-Hot tub-Near RMNP&WP

GraceRating, 5 stars1 month ago
wonderful stay! clean, cozy and close to the slopes. the gym/sauna/hot tubs were a huge plus!
Guest favourite

Townhouse in Winter Park

4.91 out of 5 average rating, 128 reviews

Ideal Winter Park Retreat – Ski, and Relax!

TinaRating, 5 stars2 weeks ago
This was a last minute weekend getaway for four of us (and a dog) and Rachel was super responsive and accommodating. We really appreciated all of the information and details shared by Rachel - it made our stay uncomplicated and relaxing! The house itself is great - exactly as written and shown and the community is peaceful and welcoming. We did read about the train but honestly, it was fun thinking about how we might be sighted by a passenger on the train and have become part of their journey! Overall, we really had a great weekend and Rachel was a big part of that. Would definitely recommend!
Guest favourite

Apartment in Granby

4.91 out of 5 average rating, 33 reviews

4 Season Perfection (New Listing)

TrentRating, 5 stars4 weeks ago
This unit is part of a multistory complex - there is a front desk to help you find your unit and get checked in. Bradley's unit is clean and has a tasteful, modern and functional kitchen and bathrooms. The unit is comfortable and has a pretty view out of both the living area and bedroom. The bed is a comfy king size. The unit is on the first floor and is a very short walk from where you park, and the athletic center with a sauna, indoor and outdoor pools and jacuzzis (also with nice views) is just 50 feet down the hall. Brad is friendly and responsive - would recommend and stay again!
Guest favourite

Townhouse in Fraser

5 out of 5 average rating, 57 reviews

Views! Hot Tub, Sauna, Deck, Huge living area!

DanielRating, 5 stars1 week ago
The stay was great for our group of 4 kids, a baby and 3 adults. Plenty of space. Everything you need in the kitchen. Purple line stop literally outside the front door. Grocery store a few minutes away right on the bus line. The views were incredible, especially in our last day waking up to snow covering the sky lights and looking over the balcony to see a beautiful landscape. We didn’t use the hot tub so can’t speak on that, only downside could be it being right in the front entrance of the buildings and not much privacy. Overall we all enjoyed our stay and watching movies at night in the comfy living area. There were a few board games the kids had fun with. Overall, great stay and would come back for sure!
Guest favourite

Townhouse in Winter Park

5 out of 5 average rating, 8 reviews

Luxury Alpine Abode | Vast Rooftop Views & Hot Tub

JamieRating, 5 stars1 month ago
The House was clean and stocked with all of the amenities we needed. We booked this place due to the proximity to down town Winter Park. We were close enough to walk shops and restaurants as well as the sledding hill and park. We were also less than 3 miles from the resort which gave us quick and easy access to mountain. The LIFT service also had 2 stops less than 1/4 mile from our location which made it easy to travel if we did not want to drive. The house has 4 floors with bathrooms on floors 1 and 3 making it a bit inconvenient. The property management company was extremely responsive. When we arrived I had quite a few questions about the hot tub, the heating elements on the 4th floor to melt the snow, the floor heaters in the rooms and a few other questions, and they responded within 20 min each question. Overall, all of the stairs is not enough to discourage us from staying in this exact location again. I'd say our stay is a 10/10 and we would definitely rent here again.
Superhost

Home in Grand Lake

4.93 out of 5 average rating, 14 reviews

Lake Front House/ Billion $ view/wood incl.

MeganRating, 5 stars5 months ago
We had a wonderful stay. The access to the lake was everything. Having kayaks and SUPs within feet of the deck created no pressure when to use them and didn’t have us on a set time of when to return them. After our trip, my pug now considers herself a water dog. Thank you so much for the wonderful retreat.
Guest favourite

Cabin in Idaho Springs

4.93 out of 5 average rating, 287 reviews

Mountain Vacation Home with Amazing views

MilesRating, 5 stars1 week ago
We had an amazing experience with Beautiful Views. Felt secluded and had a sense of privacy. There’s plenty of restaurants nearby in Idaho Springs and lots of options to make a stay here memorable.
Guest favourite

Condo in Winter Park

4.89 out of 5 average rating, 84 reviews

Winter Park Base Studio - Slope View, 200 yds to G

BaileyRating, 5 stars1 week ago
Great location. Attached underground and appeared to be heated parking. (paid for separately) , was absolutely perfect. Disappointed neither hot tub in our building or the attached building was opened, but was prepared for it both at time of booking. The kitchen was stocked with all the pots, pans, and utensils you’d need for any and all meals.
Superhost

Holiday home in Winter Park

4.8 out of 5 average rating, 64 reviews

Stylish Condo close to everything: Ski-Spa-Relax !

MargieRating, 5 stars1 week ago
We had an amazing stay at Guirec’s place! The apartment was very clean, supplied with all we needed, cozy and confortable. Guirec was very responsive to our questions. The location was perfect for exploring the city, and we would definitely stay here again.
Guest favourite

Home in Tabernash

4.91 out of 5 average rating, 114 reviews

TreeTop Getaway, Secluded Winter Park Highlands

HannahRating, 5 stars1 month ago
This cabin was fantastic for our family of 4 adults and 2 children! If we are ever back in Colorado, we will definitely be staying here again! Amber was a great host and everything we needed was in the cabin (cooking, towels, etc.). It snowed the entire time we were there and we had no issues with the drive in/out each day (but would recommend an AWD or 4WD). We had the most amazing views and felt right at home! We skied at Winter Park and that was amazing as well! 5 STARS for Amber's cabin!
Guest favourite

Townhouse in Fraser

5 out of 5 average rating, 5 reviews

Winter Skiing just 5 minutes Away

AnastasiyaRating, 5 stars1 day ago
This is an very nice condo, spacious and stocked well. The pictures don't do it justice. In a quiet neighborhood but close to anything you might need. The host responds fast. We had a wonderful time skiing at Winter Park and would absolutely love to stay at this beautiful home again.

Popular amenities for Winter Park holiday rentals

Stay near Winter Park's top sights

Winter Park Resort331 locals recommend
Mountain Grind Coffee & Bistro168 locals recommend
Hernando's Pizza Pub166 locals recommend
The Foundry Cinema & Bowl163 locals recommend
Fraser Tubing Hill130 locals recommend
Pepe Osaka's Fishtaco Tequila Bar & Grill101 locals recommend

Other great holiday rentals in Winter Park

Superhost

Loft in Granby

4.83 out of 5 average rating, 130 reviews

Ski in/out- Sleeps 8 Granby Ranch Mountainside #69

BenjaminRating, 5 stars3 weeks ago
super pleased with our stay. layout was great for us as the kids room was adjacent to ours👍👍
Guest favourite

Townhouse in Grand Lake

4.95 out of 5 average rating, 267 reviews

Amazing 180° Mtn Views

NedaRating, 5 stars3 months ago
We had a great girls weekend at the lake. The place was great, clean and Tom was a great communicator. Thanks again!
Guest favourite

Home in Granby

4.91 out of 5 average rating, 100 reviews

Grand Elk Getaway! - Mountain Views & 7 Beds!

JulieRating, 5 stars1 month ago
Great location. Near grocery store and 5 minute drive to Granby Ranch. Home is very clean and linens smell so clean & fresh. Comfy beds. Very easy check in and nice hosts.
Superhost

Chalet in Fraser

4.87 out of 5 average rating, 60 reviews

Updated Mountain Cabin

KimberlyRating, 5 stars11 months ago
Second time stay for our family; we feel right at home! Thankful for a great place with a great host in a great location! Kids are already asking when we can come back!
Superhost

Cabin in Grand Lake

4.77 out of 5 average rating, 30 reviews

Enjoy the deck, private creek, moose & lake views

KatieRating, 5 stars5 months ago
What a lovely cabin with amazing views. My favorites were the natural bubbling spring that passes through the property, the view of Shadow Mountain Lake, and well- stocked and modernized residence. The beds were difficult for each of the group to find comfort , both hardness and in maneuverability around the bed in the smaller room. (Lots of bruised thighs and hips). Better for more agile and younger folks in those bedrooms, for sure! We felt right at home and pampered. Thank you!😊
Guest favourite

Condo in Granby

4.94 out of 5 average rating, 52 reviews

Moose Hill Hideaway/Granby Ranch/CO/2 bed 2bath

CourtneyRating, 5 stars1 month ago
The lodging was perfect for a winter getaway. The fireplace was not working which was kind of a bummer, but the owners left a note with apologies. We are a family of four and were all able to sleep comfortably in the home. All the necessities were there for us and we never found ourselves missing things at home. The home was clean and exactly as described. Toward the end of our trip, guests checked in the floor above us. The floors are pretty creaky so it was louder than we would have wanted. The Granby Ranch area is absolutely beautiful. It is not too crowded if you choose to go on the slopes. Everyone was so nice and helpful from the instructors to the staff at the lodge. The grocery store nearest to us (City Market) was wonderful. It has everything you could want. Make sure to take your own reusable bag though. The towns close to the home were lovely for Christmas. I would highly recommend this home to anyone. It is well worth a visit.
Guest favourite

Home in Granby

4.97 out of 5 average rating, 33 reviews

New! Stunning 2 Bed/2 bath Home

RyanRating, 5 stars6 days ago
Great stay! Clean and well-equipped, incl. consumables like Dove shower products, condiments/spices, laundry soap, etc. Amenities (fireplace, hot tub w/unobstructed view) both SO nice after days cross-country skiing. Having a garage such a treat on cold mornings. Almost 100% as pictured - note the white towel robes are no longer provided in case you want to pack one! - otherwise very accurate. Lots of blankets, linens, pillow choices for sleeping, so bed was comfortable & customizable. 2nd BR/BA across the house from primary; nice for privacy if a group. Outstanding host - one of the best we've stayed with. We almost needed to extend by one night last-minute due to winter storms forecast (at home, ironically), for our departure day. Although we ultimately made it out on time, Sarah was SO communicative and would have rearranged the cleaners so we could stay until early the following morning. We love this area and hope to return again next year; would happily stay again!
Guest favourite

Home in Tabernash

4.91 out of 5 average rating, 79 reviews

Beautiful Mountain Home- Fast Internet and Hot Tub

RachelRating, 5 stars6 months ago
Regan was a great host and made herself available when we reached out. The house is beautiful and conveniently located nearby lots of local attractions. Although the house is in a suburban neighbourhood and not as isolated as the photos appear on the listing. We enjoyed our stay and the hot tub was lovely and relaxing! Would recommend.

Quick stats about holiday rentals in Winter Park

  • Total rentals

    1.4K properties

  • Nightly prices starting at

    $16 AUD before taxes and fees

  • Total number of reviews

    40K reviews

  • Family-friendly rentals

    1.1K properties are a good fit for families

  • Pet-friendly rentals

    250 properties allow pets

  • Rentals with a pool

    590 properties have a pool

Destinations to explore

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