Holiday rentals in Winter Park

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Top-rated holiday rentals in Winter Park

Guests agree: these stays are highly rated for location, cleanliness and more.

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Guest favourite

Cabin

4.94 out of 5 average rating, 194 reviews

Cozy Log Home,Sleeps 10. Free shuttle,3 min-slopes

Location doesn’t get better! Highly desirable area in WP. Free shuttle steps from door. Newly remodeled! Outstanding Views of slopes/Continental Divide. 3-4 min drive to slopes & 1 1/2 min-Main to Main St. shops,dining, bars, concert amphitheater/fairs etc. High-end grill, Lg Deck! New smart tv in living room w/ Sonos soundbar to play music from phone. WIFI 1 GB, cable, games. Every kitchen amenity! Our own Quality bedding/linens. Cleaned/Sanitized at each checkout! Short term license #005200

Guest favourite

Townhouse

4.95 out of 5 average rating, 22 reviews

Ski-in, Ski-out Granby Getaway! Sleeps 10!

Brand new home, Ski-in, Ski-out! Hike, Bike, Swim, Golf! Get away to the mountains for a relaxing retreat in Granby! Right at the base of Granby Ranch ski mountain ready for all your activities or enjoy happy hour and live music next-door at the Bluebird Bistro. Location is walking distance to the lift to Vista Ridge Wedding Venue. This house is great for large groups or 2 families. Sleeps 10 and can accommodate kids well. Lots of games and 3 smart TVs for streaming movies! STR Permit 007448

Superhost

Apartment

4.89 out of 5 average rating, 101 reviews

Mountain Loft-Views-Pool-Hot tub-Near RMNP&WP

Experience mountain living in this stunning Vaulted Loft Condo with top-floor mountain views. Boasting a full kitchen, balcony, new smart TV, WiFi, cable, and shared heated pool & hot tubs. With year-round activities, such as skiing, hiking, biking, and fishing nearby, there's something for everyone. Located conveniently near RMNP, Granby Ranch, Winter Park, Snow Mtn Ranch, Grand Lake, and Hot Sulphur Springs. NO PETS, NO SMOKING, with Professional Housekeeping Service for a worry-free stay.

Guest favourite

Townhouse

4.91 out of 5 average rating, 124 reviews

Ideal Winter Park Retreat – Ski, and Relax!

This fantastic end-unit townhouse offers the perfect blend of convenience and serenity. Located on the shuttle line and just minutes from town, it’s nestled among towering pines for a peaceful, secluded feel, yet close to all the action. Featuring stunning mountain views, this light and bright home includes: private hot tub with views, fully-stocked kitchen, and split level bedrooms for privacy. The perfect base for all your Winter Park adventures—whether skiing or just unwinding in nature!

Guest favourite

Flat

4.93 out of 5 average rating, 30 reviews

4 Season Perfection (New Listing)

NEW LISTING with a former 4.97 Airbnb rating! Perhaps the nicest 1 bedroom, 2 bathroom condo in the entire Valley (Winter Park/Fraser/Granby). Ideal for a couple, 2 couples a group of friends, or a family, we promise this condo will not disappoint. With 2 full bathrooms, a king bed in the master bedroom, and a comfortable pull out couch in the living room, there is plenty of space for your group. Fully updated bathrooms and kitchen are a perfect finishing touch to this beautiful condo.

Guest favourite

Townhouse

5 out of 5 average rating, 55 reviews

Views! Hot Tub, Sauna, Deck, Huge living area!

Ideal for families or groups Spacious abode near Winter Park Ski Resort (10-min drive) Stunning mountain vistas Sauna Steam shower Hot tub Recently updated for guest comfort 1850+ sq ft home Free, fast wifi and cable TV Stocked kitchen Convenient access to free bus line Ample parking, including a garage spot Low taxes (just 6%) Washer/dryer included Detached Garage for Gear or Car storage Our home has a strict No Smoking policy. A $500 fine and additional cleaning fees will apply.

Guest favourite

Townhouse

5 out of 5 average rating, 7 reviews

Luxury Alpine Abode | Vast Rooftop Views & Hot Tub

Luxury Alpine Abode is a stunning 2,000 sq. ft. loft in Winter Park’s new ROAM neighborhood, featuring panoramic mountain views, a rooftop hot tub, and cozy fire pit. Perfect for up to 10 guests, with two master suites, a chef's kitchen, and spacious living areas. Steps from downtown and a quick shuttle to Winter Park Resort, it's the ideal retreat for families or friends seeking luxury and adventure. #LuxuryAlpineAbode #WinterPark #MountainViews #HotTub #GroupGetaway #SkiAndStay

Guest favourite

Cabin

4.93 out of 5 average rating, 285 reviews

Mountain Vacation Home with Amazing views

This cozy cabin is close to family-friendly activities. You’ll love your stay because of the the views, high ceilings, privacy and the location. The cabin is great for couples, solo adventurers, and families (with kids) There are TVs with cable in the bedrooms and living room, a hot tub to soak in and enjoy how close the stars shine. PLEASE NOTE: This Vacation home's elevation is 10800 feet. The weather is unpredictable- From September to May 4 wheel drive is required!

Guest favourite

Apartment

4.89 out of 5 average rating, 81 reviews

Winter Park Base Studio - Slope View, 200 yds to G

Base of Winter Park, slope view, 2mins from Gondola! ## New Hot Tub opens January 24th! * king sized bed * in-room AC system * king sized sleeper sofa (American leather, no springs, high end design) * shared 30 person hot tub * fast internet * TV * granite counters * professional artwork Check-in 4pm. Rental agreement must be signed within 24 hours, keycodes not given w/o signed agreement. $100 security deposit reqd. Paid parking reqd. (WP Rental Reg #006076)

Superhost

Holiday home

4.79 out of 5 average rating, 61 reviews

Stylish Condo close to everything: Ski-Spa-Relax !

Welcome to our charming Scandinavian condo in the heart of Winter Park, Colorado! Recently remodeled, this cozy retreat is just 200 yards from the free ski shuttle. With a fireplace, direct walking access to restaurants, and a peaceful setting amount aspen trees and spruces, this is the perfect place to unwind after a day on the slopes. Plus, you'll have access to a spa with hot tub and sauna for ultimate relaxation. Book now for an unforgettable winter getaway!

Guest favourite

Home

4.91 out of 5 average rating, 114 reviews

TreeTop Getaway, Secluded Winter Park Highlands

Panoramic Continental Divide & Winter Park Ski Resort views from this 4 bed, 3.5 bath home perched at the top of Winter Park Highlands. Ideal open floorplan with 3 living areas, including loft and game room, vaulted ceilings, main level master suite. Enter right onto the main floor. Enjoy spectacular views from the spacious decks or cozy up in front of the fireplace! Close to town and perfect for the whole family to enjoy!

Superhost

Townhouse

5 out of 5 average rating, 3 reviews

Winter Skiing just 5 minutes Away

Now THIS is a destination! This beautiful 3 Bedroom / 3.5 Bath condo is set up for any occasion. The area is quiet, peaceful, and just minutes away from so many attractions. The night skies are lit up with stars, the daytime is filled with blue skies 300 days a year. Summers are warm and pleasant, fall brings the most amazing colors, winter gets blanketed in snow, and springtime is for wild flowers!