Holiday rentals in Winter Park
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Top-rated holiday rentals in Winter Park
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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)
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!
Top Floor Condo Steps From Free Shuttle w/Hot Tub
Two bedroom, Two bath, top floor condo with three private balconies. Our fully equipped kitchen comes complete with all the amenities you need to prepare your favorite meals, and we provide complimentary toiletries for your convenience. 15 minute walk to main street bars and restaurants and on the free ski shuttle line to the Mountain or Main Street. Take advantage of our free parking in front of the building and unwind after a long day on the slopes or trails in the community outdoor hot tub.
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!
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
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.
New 2BD/2BA w/AC: Walk to Restaurants + Shopping!
Contemporary Timber Fox 2 Bedroom (both w/ King Beds)/2 Baths + sleeping alcove located in the heart of downtown Winter Park with a consistent 5 STARS!! WALKING DISTANCE: 1 block to Main Street and many restaurants, breweries, 2 blocks from Cooper Creek shopping center. SUMMER FUN! Steps from Hideaway Park for Free Thursday Summer Concerts or weekend events. Easy drive to Rocky Mountain National Park! Easy access to Fraser River Trail. Large HOT TUB & fire pit available on property.
Luxury Winter Park Retreat with Private Hot Tub
Welcome to your mountain escape in the heart of Winter Park. This newly built townhome is just 8 minutes from Winter Park Ski Resort, offering the perfect balance of adventure and comfort. After a day on the slopes or trails, unwind in your Private Hot Tub as the mountains glow around you, then head inside to relax by the fireplace with friends and family. With open living spaces, this home was designed for memorable mountain stays. Winter Park Short Term Rental Registration No 029388
Luxury Winter Park Studio*PrivHotTub*Majestic View
Brand New Studio styled in HIP MOUNTAIN CONTEMPORARY in EXCLUSIVE Leland Creek! Perched amongst the aspen trees with spectacular sunset views,you'll never want to leave your own private Hot Tub and Deck!Floor to ceiling windows with stunning mountain views,Room+Board furniture and rustic ski vibe fill the home with a Contemporary Chic style.Private Entrance.Good Pets are welcome.10miles to Granby.18 miles to Grand Lake+Rocky Mountain National Park.DenverInternational airport 1.5 HR.
Mountain Cabin
Our mid-century-inspired cabins offer guests their own sanctuaries to stay cozy all four seasons. Tall ceilings, beautiful birchwood throughout, special touches like a soaking tub, custom Malm fireplaces , ski mountain views — you experience a better kind of mountain life when you stay with us. Our restaurant, bar & outdoor deck are open to the public. Mountain Cabins offer a more social experience, and include the option for 2 ADA access cabins upon request at the property.
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.
Founders Pointe 4355 Ski In Ski Out Winter Park
Founders Pointe is located across from the Base at Winter Park Resort Village and is considered ski in ski out condominium. The 10-person gondola at Winter Park Ski Resort is 200 yards from the lobby door of Founders Pointe. Take a break from skiing and walk back to the condo for lunch or to warm up. Winter Park Resort Base Village also has shopping, restaurants, and bars for your entertainment Permit Number: 017522
Popular amenities for Winter Park holiday rentals
Other great holiday rentals in Winter Park
Summer Escape • Riverfront Stay in WP
Winter Park Condo on the River: Walk to Downtown!
The Perch | Cozy + Modern Cabin w/ Hot Tub
Downtown WP Cabin 28 - Hot Tub - Views - Bunks
Cosmic Cabin: Views, Trails, HotTub by Winter Park
Cozy Fraser Cabin w/ Views & Moose Sightings!
A-Frame | 15 min to Winter Park | Private Acre
Luxury 3BR Winter Park | Hot Tub | Ski Shuttle
When is the best time to visit Winter Park?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $341 SGD | $357 SGD | $329 SGD | $219 SGD | $206 SGD | $218 SGD | $250 SGD | $223 SGD | $224 SGD | $232 SGD | $262 SGD | $375 SGD |
| Avg. temp | -7°C | -7°C | -3°C | -1°C | 4°C | 9°C | 13°C | 12°C | 8°C | 2°C | -3°C | -7°C |
Frequently Asked Questions
What are the best places to stay in Winter Park?
Winter Park has inviting neighborhoods near ski slopes, scenic mountain views, and easy trail access. Many visitors choose to stay around the resort area or in town for walkable dining, shopping, and outdoor activities.
What are the best things to do in Winter Park with kids?
Families frequently enjoy sledding, snow tubing, and exploring playgrounds in the winter. In warmer seasons, mini-golf, adventure parks, and guided nature walks are often suggested for younger travelers.
What are some of the best things to do in Winter Park?
Explore the slopes at Winter Park Resort, hike scenic trails, and experience mountain biking or fishing in alpine lakes. Art galleries, local shops, and seasonal festivals add variety throughout the year.
How is the weather in Winter Park?
Winter Park has cold, snowy winters with temperatures ranging from 11 to 36°F (-11 to 2°C), while summer afternoons warm to 62–68°F (17–20°C). Spring and fall are cooler and may bring brief rain or scattered snow.
When is the best time to visit Winter Park?
Winter Park is frequently suggested in winter for skiing and snowboarding, while summer attracts mountain bikers, hikers, and festival goers. Spring and fall bring quieter trails and crisp mountain air.
What are the best places to visit in Winter Park?
Travelers often explore Winter Park Resort, stroll through Hideaway Park, and wander the town’s local art galleries. Seasonal farmers markets and community spaces are also popular gathering spots.
What are some hiking trails in Winter Park?
Winter Park has several frequently suggested hiking trails, including the Fraser River Trail, Jim Creek Trail, and trails around Berthoud Pass. Alpine forests, wildflowers, and broad mountain views make hiking a favorite activity.
What are some family activities we can do in Winter Park?
Families can explore scenic bike paths, visit adventure parks, and try out nearby wildlife watching areas. Guided tours, fishing experiences, and seasonal community events bring people together year round.
What are some of the best day trip ideas from Winter Park?
Day trips from Winter Park often include exploring mountain lakes, small towns with historic main streets, or natural hot springs tucked in scenic valleys. Outdoor parks and wildlife areas around the region are also popular.
Are there any pet friendly accommodations available in Winter Park?
Winter Park has pet-friendly vacation rentals in neighborhoods near the resort, main street, and park areas. Many hosts welcome dogs, and outdoor trails make it easy to explore with your companion.
What are some local tips for visiting Winter Park?
Layer clothing for changing mountain weather, and bring sunscreen for high-altitude sun. Exploring early in the day is often recommended for quieter trails and wildlife sightings.
What is Winter Park known for?
Winter Park is known for its ski resort, mountain biking terrain, and vibrant outdoor recreation. Seasonal festivals, art spaces, and alpine scenery make it a favorite destination for adventurers.
What are the best hidden gems to explore in Winter Park?
Wander quiet trails near local creeks, discover tucked-away parks, or seek out small art galleries and coffee shops just off the main street. Lesser-known fishing spots and forested picnic areas reward curious explorers.
What are the best foods to try in Winter Park?
Try locally inspired dishes such as hearty chili, Rocky Mountain trout, and fresh baked pies in area cafes. In winter, warming stews and hot cocoa are frequently suggested favorites.
What should I bring for a trip to Winter Park?
Bring layers for temperature changes, sturdy shoes for outdoor activities, and sunscreen for higher elevations. In winter, pack gloves, a warm hat, and waterproof gear for snow sports.
What is the nightlife in Winter Park like?
Winter Park has lively bars, casual lounges, and venues hosting local music around the town center. Après-ski gatherings and group-friendly restaurants create a relaxed evening atmosphere.
What are the most popular events or festivals in Winter Park?
Winter Park has recurring music festivals, mountain bike races, and art fairs, often anchored around summer weekends and winter holidays. Seasonal celebrations bring live entertainment and local flavor to community spaces.
Are there family friendly vacation rentals in Winter Park?
Winter Park has a range of family-friendly vacation rentals near town, ski lifts, and recreation areas. Many spaces include additional amenities and flexible layouts for groups traveling with children.
Quick stats about holiday rentals in Winter Park
Total holiday rentals
Explore 1,650 holiday rentals in Winter Park
Nightly prices starting at
Winter Park holiday rentals start at $78 SGD per night before taxes and fees
Verified guest reviews
Over 49,430 verified reviews to help you choose
Family-friendly holiday rentals
1,310 properties offer extra space & child-friendly amenities
Pet-friendly holiday rentals
Find 270 rentals that welcome pets
Holiday rentals with a pool
470 properties feature pools
Rentals with dedicated workspaces
1,030 properties have a dedicated workspace
Wifi availability
1,640 of Winter Park holiday rentals include wifi access
Popular amenities for guests
Guests love Self check-in, Gym and BBQ grill across Winter Park rentals
4.8 Average rating
Winter Park stays are highly rated by guests – averaging 4.8 out of 5!
Destinations to explore
- Rentals with pools Winter Park
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- Rocky Mountain National Park
- Red Rocks Amphitheatre
- Breckenridge Ski Resort
- Coors Field
- Empower Field at Mile High
- Arapahoe Basin Ski Area
- Vail Ski Resort
- Keystone Resort
- Colorado Convention Center
- City Park
- Ball Arena
- Beaver Creek Resort
- Winter Park Resort
- Loveland Ski Area
- Pearl Street Mall
- Ski Cooper
- Granby Ranch
- Denver Zoo
- University of Denver
- Fillmore Auditorium
- Golden Gate Canyon State Park
- St. Mary's Glacier
- Denver Botanic Gardens
- Elitch Gardens