The town of Winter Park, also known as Downtown Winter Park, is located just two miles from Winter Park Resort, and is a wonderful choice for families and groups who want to enjoy an equal share of on and off-slope activities during their Winter Park vacation.
Offering the largest selection of lodging options in the local area, Downtown Winter Park vacation rentals range from one bedroom condos, to seven bedroom mountain retreats.
Trailhead Lodges is a modern, attractive collection of high-end condos in central Downtown Winter Park. The #1 spot for music festival lodging in the summer, many of our homes overlook Hideaway Park. Winter guests love the free sledding hill at Hideaway Park and free shuttle service to Winter Park Resort, that stops just outside the complex.
All of our 1 – 3 bedroom Trailhead Lodges condo rentals enjoy free access to the complex clubhouse with outdoor pool, hot tub, fire pit and workout room.
Bear Crossing is a newer town home development, set in a peaceful neighborhood above Downtown Winter Park. Ideal for families and small groups, these lovely homes back onto hiking and biking trails in the National Forest and enjoy beautiful views of the Continental Divide.
All of our Bear Crossing vacation rentals are high-end, 3 bedroom/3 bathroom homes, with either a private hot tub or jetted bathtub, heated one car garage and rich mountain furnishings and decor.
Telemark is a recently built condo and townhome development located at the North end of Downtown Winter Park, near the Fraser River Trail, Fireside Market and infamous Hernando’s Pizza restaurant.
All of our 1-3 bedroom Telemark vacation rentals enjoy a private garage, modern kitchens, private washer and dryer and easy access the free shuttle service to Winter Park Resort. Some of our Telemark vacation homes also feature a private hot tub.
Sawmill Station claims an enviable location in Downtown Winter Park, just off Hideaway Park for summer music festivals and right on the free bus shuttle service to Winter Park Resort.
All of our 3 & 4 bedroom Sawmill Station town homes offer three levels of living space plus a private garage and private balcony with gas grill. Some of our Sawmill Station townhomes also enjoy a private outdoor hot tub.
Red Quill Village is a small but very nicely constructed neighborhood in the heart of Downtown Winter Park.
Located one block back from the main street (US HWY 40), our 3 & 4 bedroom Red Quill vacation rental homes feature a private hot tub, elegant furnishings, private garage and enviable location for your next ski trip or summer getaway.
High Country Haus is one of the original condominium developments in Downtown Winter Park. Made up of many buildings and located just to the North of main street, it is within easy walking distance to the movie theater, great restaurants and shops and the Fraser River Trail.
Our vacation rentals at Hi Country Haus are all remodeled and updated, 1-3 bedroom condos with full kitchens, wood burning fireplaces, and easy access to Winter Park Resort via the the free bus shuttle service.
All of our Hi Country Haus vacation condos enjoy free access to the clubhouse with indoor pool, hot tubs and fitness room.
Our large mountain homes offer the perfect backdrop for your next family reunion or corporate retreat.
Ranging from 3-7 bedrooms in size, each of these private homes offer multiple social spaces, luxurious decor and high-end amenities. If you’ve ever dreamed of taking the family to a big cabin in the woods, or are seeking the perfect executive retreat, these Winter Park luxury vacation homes might be just what you are looking for.
Click below to view our 3+ bedroom luxury vacation homes in downtown Winter Park.
A small yet vibrant mountain town with many year round amenities: