Holiday rentals in Winter Park

4.98 out of 5 average rating, 164 reviews

Townhouse in Winter Park

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)

4.93 out of 5 average rating, 135 reviews

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

Superhost

Cabin in Winter Park

4.84 out of 5 average rating, 599 reviews

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.

4.87 out of 5 average rating, 227 reviews

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.

Guest suite in Winter Park

4.98 out of 5 average rating, 470 reviews

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.

4.9 out of 5 average rating, 183 reviews

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.

4.96 out of 5 average rating, 112 reviews

Apartment in Fraser

Walk to Restaurants! Bring your Fishing Poles!

There is still availability this weekend for peak leaf season!!! Don’t miss this spacious 1 BR Fraser condo perfectly located for your fall adventures; National Park visits, hiking, biking, and other recreation in Grand County! The pond is stocked with fish! You are just a short walk from Safeway, restaurants, breweries and the Fraser River and Trail. You are a .8 mile walk from the train station which offers daily Amtrak service and are steps away from the free Lift shuttle service.

4.99 out of 5 average rating, 140 reviews

Home in Winter Park

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.

4.83 out of 5 average rating, 214 reviews

Main Street Luxury: Downtown with Hot Tub, Trails

You'll feel right at home at the hearth of this updated condo. You'll be on the slopes in two bus stops with pickup just outside. On Main Street, across from Cooper Creek and the Rendezvous Event Center, the town awaits. Host family style feasts with the fully equipped kitchen and dine up to nine. Relax in the hot tubs, on the huge couch by the big screen digital cable TV with streaming services, on the deck and in the hot tubs. Decadent Cal King bed in master. Ski lockers.

4.91 out of 5 average rating, 147 reviews

Townhouse in Winter Park

Spacious Mountain Townhome | Private Hot Tub

Prepare for a mountain retreat in this beautiful 3 bed/3 bath townhome + private indoor hot tub. Downtown Winter Park just 3 blocks off main street where you will find many shops, restaurants, bars, city parks and entertainment for the entire family. The perfect fit for families/groups looking for space to spread out, a stocked kitchen to cook in, and a hot tub to unwind in at the end of an amazing day. Only 5 minutes from Winter Park Resort and near the free bus line!

4.96 out of 5 average rating, 446 reviews

Guest suite in Fraser

Spring into summer at Madge’s. 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; Fraser Valley has them in spades! After enjoying a perfect Colorado summer day, come back to your spacious room for a drink on your private patio to think about what restaurant to enjoy to cap a wonderful day.