Vacation rentals in Winter Park

Charming Rocky Mountain A-Frame

The Woodland A-Frame Retreat is NEWLY RENOVATED as of December 2021. It features a tranquil and private setting tucked amongst the 1 acre lot's aspens and pines. Byer’s Peak mountain views from the front deck. Located on the free shuttle route (the Lyft stop is two houses away!) and a bike ride away from Idlewild Trail system. Open living area with loft, granite countertops, stainless steel appliances, washer/dryer and a cozy wood stove. Enjoy all the modern comforts with a rustic a-frame charm.

Modern/Rustic 2-bedroom Townhouse + Bonus Loft

Newly renovated modern/rustic three-story A-Frame townhome on the free shuttle route. Small and cozy, this 2 bedroom (+ loft) space can comfortably accommodate 5, but it should be noted that there's only 1 full bathroom! The location is perfect: it's quiet and serene while only being minutes from downtown Winter Park and two miles from the WP Resort. Vasquez Road is .4 miles from the front door to access everything the National Forest has to offer (hiking, snowshoe excursions, mountain biking)

Tipsy Fox @ Downtown Winter Park Near the Slopes!

Welcome to the perfect Winter Park getaway! Located in downtown, this cozy one-bed, one-bath condo is just steps away from Hideaway Park and its year-round free events. With 3 queen beds, including a sleeper sofa and a Murphy bed, it comfortably sleeps 6 guests. Enjoy the heated garage and ski locker for your vehicle and snow gear. After outdoor activities, unwind in the hot tub, gather around the fire-pit, or relax on the balcony. Conveniently close to food, slopes, tubing hill, and amenities!

Cozy mountain retreat in downtown Winter Park

Lovingly remodeled Hi Country Haus 1 bedroom 1 bathroom condo central to downtown Winter Park. Use our Tiny Mountain Retreat as a launchpad to all the local access Winter Park has to offer or as a space for rejuvenation in this beautiful mountain town. Incredible access to local trail running, mountain biking, backpacking, fly-fishing, hiking and skiing. Grand Lake and Rocky Mountain National Park are easily and often visited from our spot as well. WP Short-term rental registration #019404

Scandinavian-Inspired Escape: Modern Cabin w/ Spa

Escape to our Modern Mountain Home in Grand County, Colorado, where luxury meets wilderness! Nestled amidst majestic mountains, this Scandinavian-inspired retreat offers the perfect blend of rustic charm and contemporary comfort.  Wake up to breathtaking views, with hiking, biking, and skiing right outside your door.  Highlights: • Panoramic mountain views • Close to Winter Park & RMNP • Scandinavian-inspired design • Wood-burning fireplace • Private hot tub Grand County Permit #106884

Cozy Cabin in Perfect Location

You've found the perfect cabin for your trip to Winter Park. Cozy, w/a queen bed & a single, pull-out couch. Small kitchen or -on a nice day- grill on back deck near creek. Electric fireplace adds ambiance. Tiny kitchen w/appliances, Keurig &dishes. STEPS away from Cooper Creek Town Square restaurants & Hideaway Park’s concerts. The City of Winter Park has trains going through the town, which adds to the charm. We love pets/dogs! 2 or more dogs require extra $10 per dog one-time cleaning fee.

Rustic Glam Mountain Escape - Near Downtown/Trails

Renovated mountain townhome hosted by experienced, 5-star Superhosts! After exploring nature and enjoying downtown Winter Park, soak your tired legs in the private, indoor hot tub. Kick up your feet, and nestle up in front of the crushed glass fireplace. Enjoy the mountain views and warmth of the afternoon sun in the solar room. Cook a gourmet meal in the brand new granite/stainless steel/marble kitchen. Do it all over again after laying your head down to rest on luxuriously-appointed beds!

Charming Suite in Old Town Winter Park

Charming European suite steps away from a major ski resort. Located in the heart of Old Town Winter Park this beautiful European Country home is a welcoming retreat for mountain visitors. OUR LARGE PRIVATE SUITE IS IN THE LOWER LEVEL OF OUR HOME, complete with separate bedroom, kitchenette, hot tub, bathroom/shower & FREE PARKING! Take a 10-15 minute walk or short bus ride to the base of the Winter Park Resort to experience incredible skiing and boarding at any of the Resort's Territories.

Best Views In WinterPark | FamilyFriendly | Garage

COME FOR THE FUN AND STAY FOR THE BEST VIEWS IN WINTER PARK :) Your 3BR/3BA 1,300+ sqft Family Friendly Condo with Private Garage lives like a Townhome with ample space & privacy for everyone in your group. Upstairs you'll find a fully private master bed with ensuite bath. The 2nd bedroom is super private located right off the entryway with it's own private ensuite full bath as well. At the Winter Park Retreat you'll enjoy spectacular views from your private deck and throughout the home.

30 mi to Rocky Mt- 270* Views - Private Hottub

Welcome to the Alpenglow Mountain Gateway! In this funky mid mod 2 bedroom/ 2 bathroom townhome you will find all the creature comforts within the confines of our beautiful wood paneled solar townhome. Private hottub!! Every room is complimented by the expansive mountain views. Eastward is Byers Peak & West the Continental Divide, making sunsets/ sunrises an unmissable time. WP resort 9 mins away Bus stop right outside door Less than a mile to market, restaurants and beer Permit: 6424

Winter Park Studio: On the River~ Walk Downtown!

Fireside Haven is a cozy studio located on a secluded spot RIGHT on the Fraser River, yet is walkable to all that downtown Winter Park has to offer. Dine-out, shop, enjoy coffee at a café, cocktails at happy hour, hike/bike and catch the ski shuttle all within a five-minute walk from your front door! You will have a king-size bed, queen-size sofa sleeper, full kitchen, bathroom, fireplace, private patio & ski closet.

Updated Condo | Washer Dryer | Steps to Shuttle

This 1 bed 1 bath condo provides all the essentials for your stay and the light and open floor plan makes you feel right at home. Located walking distance from trails, shuttle stop, supermarket, coffee shops, local restaurants, and just an 8-minute drive to the base of Winter Park. A small pond with benches and mountain views sits behind the unit, offering additional outdoor space right at your fingertips.