Ski-in/Ski-out holiday rentals in Winter Park

Beautiful Spacious 2 Bedroom & Loft Mountain Condo

Located right in the middle of all things Rocky Mountains. You're just 30 minutes from Grand Lake/Rocky Mountain National Park/Winter Park and 2 mins from skiing, fishing, golf, and mountain biking at Granby Ranch. This corner unit has lots of space at 1200 square feet. Between the king size bed in the master, a queen bed in the 2nd bedroom, and a queen size sleeper sofa in the upstairs loft, the condo is able to sleep 6. We only allow 4 guests, but could accommodate on a case-by-case basis.

Granby Ranch Getaway – Trails, Hot Tub & Firepit

Freshly remodeled in July 2025, Sundog Condo is your cozy ski-in/ski-out retreat at Granby Ranch – just 20 mins to Rocky Mountain National Park, Grand Lake & Winter Park. Enjoy a king bed with Brooklinen linens, fully stocked kitchen (Nespresso, quality cookware), gas fireplace, Roku TV, and patio with firepit. Year-round hot tub steps away; pool & gym access available. Walk to ski lifts; trails, golf, fishing, biking, hiking & skiing/Nordic trails right outside your door - adventure awaits!

Ski In/Ski Out - Modern Cozy Condo in Winter Park

Welcome to Leone’s Den. This newly renovated studio condo located at the base of Winter Park Resort. Walk less than 150 yards to the slopes! Shops, restaurants, and bars at the Village Base just across the street and a pool sized hot tub! Marvel at the beautiful mountain views from the largest hot tub in Winter Park, brand new in 2025. Enjoy the view of village and mountain landscape while enjoying the warmth of the fireplace. The studio has everything you need for an unforgettable stay.

Riverfront Condo☆1st Floor☆Ski Bus☆Pool & Hot Tub

1st floor condo with views and sounds of Fraser River. Walking distance to downtown Winter Park grocery store, coffee shop, restaurants, breweries, retail stores, bars, movie theater, and bowling alley. Community amenities include an indoor pool, hot tubs, workout room, lounge with pool table, laundry facilities, and outdoor playground. Free bus to resort nearby. It is a great place to curl up next to the electric fireplace, relax, and unwind after a full day of outdoor activities.

One Bedroom Condo - Winter Park Resort Base Area

Hit the slopes early on a powder day! If you need to pop back for a quick lunch, our condo’s convenient location makes it perfect for families. After an adventure-filled day, unwind in the oversized hot tub! As a spacious corner unit, this condo offers more room than standard 1-bedrooms. You’ll sleep comfortably on the king-size Tempurpedic bed, and the living room sofa easily converts into a queen pull-out bed for extra guests. Winter Park Short-Term Rental Registration No. [004361}

Luxury Mtn Cabin/Free Shuttle/ Views/Garage

Escape to Mountain Flower Cabin located in the Rendezvous community just a short walk to downtown Winter Park and a 4 mile shuttle ride (free) to Winter Park Ski Resort. Our 3BR cabin is well appointed with custom furniture, modern amenities, and breathtaking mtn views. Nestled within the Rendezvous Trail System, alongside the Fraser River, you'll find miles of hiking, biking, fishing and cross country skiing right outside your door. The free shuttle to WP is steps from the cabin.

Michael’s Dream Views in Winter Park, CO condo #15

Located in Downtown WP, Condo 15, top floor, awesome views, in Hi Country Haus Condominiums, Lic#009357. Check out WP resort website for exciting improvements. World class skiing, biking, hike, fish, restaurants, shops, breweries, Hideway Park (sledding hill, Concerts, skateboard). WALK TO Fireside Grocery Market, Foundry Movies/Bowling/Pizza, Grand Park Rec Center and more. HCH has exclusive Rec center. WP RESORTS FREE BUS, pick up across our parking lot.

One Bdrm Condo Ski In / Ski Out, Hot Tub, Fire Pit

Located in the Winter Park Village, walking distance to The Gondola this condo has it all! The bedroom features a King bed with a memory foam pull out Queen in the living area. Complete Kitchen, full size fridge, dishwasher, large bathroom, and private covered patio with views of the Mountain. Walking distance to shopping, restaurants, & activities! One of only a handful of units with direct outdoor access. UPDATE: New hot tub is OPEN! Permit #009238

Top floor, larger 1 bedroom in Winter Park Village

Conveniently located in the Winter Park Village at Fraser Crossing, this updated and oversized 1 bedroom condo sleeps 4 comfortably with a FULL KITCHEN!!! Enjoy the views that come with this peaceful and conveniently located penthouse unit. Close to entertainment, activities, restaurants, ice skating rink, and adventure! Most importantly, a short 2 minute walk to the Gondola...park your car and forget about it.