Family-friendly holiday rentals in Winter Park

Modern Cabin w/ Hot Tub & Garage - Minutes to Mtn

2BR townhome with a loft in a woodsy neighborhood in Winter Park/Fraser. Want a relaxing scenic place to sit by the fire or enjoy Grand County's outdoor adventures? Come stay and enjoy this townhome with access to free shuttle transportation during the winter. Both bedrooms include King beds. The loft includes a daybed that expands to a king bed and the sofa pulls out to a bed. PRIVATE 7 PERSON HOT TUB on patio. Propane Grill, easy access to hiking/biking trails, restaurants, stores, bars, etc.

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 (+ lofted bed) 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)

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

Homebase Snowblaze

Enjoy the magic of the Fraser River Valley and charm of downtown Winter Park from our well-equipped, completely remodeled studio. Only an hour and thirty minute drive from Denver International Airport. Walking distance to Winter Park's Main St. lined with shops and dining and a quick 5 minute drive to the world class slopes of Winter Park resort. Take advantage of the free "Lift" bus, with a stop right out front of the building and a ride to the resort in less than 5 minutes. WP STR # 009036.

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

Winter Park Creekside Chalet with Hot Tub

Experience nature in this scenic 4-bedroom, 3-bathroom chalet that is secluded amongst the trees and river yet close to everything. Choose having your morning beverage nestled in front of the fireplace or in a hot tub overlooking the river. The property is perfectly situated with downtown 1 mile away, Winter Park Resort within a 10 minute drive and 75 steps from the Lift bus route too. Or, stay around the house with access to beautiful hiking and mountain biking trails just 1 block away!

Pool Access & Mtn View! Luxe WP Cabin, Near Trails

Rendezvous Neighborhood | 1 Mi to Dtwn Bites & Brews | Walk to Fraser River Adventure begins right out your door at this Winter Park vacation rental, where alpine trails and fresh air set the stage for an unforgettable stay. Hike and bike through scenic terrain, or take advantage of Club MeadowRidge amenities just a short drive away. Then return to unwind in a beautiful cabin thoughtfully designed with custom furniture, modern amenities, and epic views. This is mountain living at its best!

Prime location, amazing views, stylish, sleeps 7

Relax and unwind at this stylish, centrally-located condo. Features include an updated kitchen as well as both bathrooms, a cozy fire place, spacious patio to enjoy morning coffee with incredible views all season. Located just 0.5 miles from downtown Winter Park you can easily walk to restaurants and shops. A shuttle stop to Winter Park Resort is conveniently located just outside the front door making the slopes just minutes away. Easy access to biking/hiking trails as well as Wolf Park.

Madge’s Studio Pets welcome!

Whether it be play time or quiet time (or both!), we offer our guests (and pets) the comfort of a large studio and yard at the end of a dead end street. You have a beautiful mountain setting with easy access to all your favorite summer activities. In addition, we are 45 minutes from Rocky Mountain National Park and the lakes of Grand Lake. After enjoying a perfect Colorado day, come back to your spacious room for a drink on your private patio to think about what restaurant to enjoy.

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

Leone’s Den | A Boutique Mountain Retreat at the Base of Winter Park Resort Step into refined alpine comfort at Leone’s Den, an elegant studio just steps from the slopes. Located across from the Village Base, enjoy easy access to dining, shopping, and après-ski, then retreat to a warm space with a cozy fireplace and elevated finishes. Relax in Winter Park’s largest hot tub and return to plush linens and beautiful mountain and village views.

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.

The Mountains are calling!

Cute studio with everything you need. The bed is a murphy bed, very comfortable. Comfy couch with ottoman. Kitchenette, bathroom. This property is very simple. Close to trails to trails and the town of Winter Park and Fraser. You might even see some wild life! Leave your worries behind and get in the zone! Rise with the sun, Sleep with the stars, Always create fireworks!