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Winter Park vacation rentals

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Top-rated vacation rentals in Winter Park

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

Condo · Winter Park
Peaceful Condo Near Downtown and Miles of Trails
Perfect for couples getaway or small family. Arapahoe National Forest trails are located steps away. Walk or take a short bike ride to Main St. in downtown Winter Park. Clean and cozy condo with a brand new kitchen stocked with all the essentials. Main entrance at ground level, bedroom on 2nd floor. Also includes a nice patio for an evening dinner outside. Come spend a quiet weekend in the mountains! STR registration number #007090
Oct 31 – Nov 7
$66 per night
Superhost
Apartment · Winter Park
Downtown Condo w/ Shared Pool/ Hot Tub/ W/D & WiFi - Free Shuttle WP Resort
 
Oct 17 – 24
$67 per night
Condo · Winter Park
Winter Park Studio: On the River~ Walk to Downtown
Fireside Haven is located on a secluded spot RIGHT on the Fraser River, yet is walkable to all that downtown Winter Park has to offer! You will have a king-size bed, queen-size sofa sleeper, full kitchen, bathroom, fireplace, private patio & ski closet. Walk to ski shuttle stop, hiking/biking trails, fishing, restaurants, grocer, bars, breweries & nightlife.
Nov 6 – 13
$134 per night
Superhost

Vacation rentals for every style

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Stay near Winter Park's top sights

Photo of Winter Park Resort
Winter Park Resort107 locals recommend
Photo of Winter Park Pub
Winter Park Pub23 locals recommend
Photo of Rendezvous Event Center
Rendezvous Event Center13 locals recommend
Photo of Cooper Creek Square
Cooper Creek Square33 locals recommend
Photo of Hernando's Pizza Pub
Hernando's Pizza Pub98 locals recommend
Photo of Randi's Grill & Pub
Randi's Grill & Pub35 locals recommend

Winter Park home rentals

Home · Winter Park
Cozy Condo on Fraser River Downtown Winter Park
Oct 25 – Nov 1
$62 per night
Home · Winter Park
the glasshouse
Jan 27 – Feb 3
$797 per night
Superhost
Home · Fraser
Central and Cozy Townhouse
Oct 27 – Nov 3
$101 per night
Home · Fraser
Relax and Have Fun in Our Beautiful Home
May 7 – 14
$315 per night
Superhost
Home · Fraser
Rendezvous Luxury Cabin | Private Hot Tub | Outdoor seating area | 2185 Pioneer
Oct 27 – Nov 3
$219 per night
Superhost
Home · Tabernash
Townhome near Winter Park, Granby & Devils Thumb
Oct 28 – Nov 4
$126 per night
Home · Winter Park
Winter Park Creekside Chalet with Hot Tub
May 3 – 10
$641 per night
Superhost
Home · Granby
Granby Ranch Ski in/ski out family cabin
Oct 28 – Nov 4
$97 per night
Superhost
Home · Fraser
Mtn Views, Trail Side & Private Hot Tub!
Nov 28 – Dec 5
$334 per night
Home · Winter Park
Dog-friendly nature getaway near dining w/pool, hot tub, stream-view balcony
Aug 16 – 23
$221 per night
Home · Granby
New Luxury Chalet #94 Near Resort/Hot Tub & Great Views - FREE Activities & Equipment Rentals Daily
Apr 19 – 26
$293 per night
Home · Fraser
Fraser Home with River & Mountain View
Oct 4 – 11
$323 per night
Superhost

Winter Park summer vacation rentals

Condo · Fraser
♥︎Kid Friendly on Winter Park Bus Route with W/D♥︎
Oct 21 – 28
$83 per night
Superhost
Condo · Winter Park
Downtown Winter Park Ski Condo Studio Snowblaze
Oct 12 – 19
$52 per night
Superhost
Condo · Winter Park
Luxury on Main St +Hot Tub +Steps to Brew & Trails
Oct 25 – Nov 1
$62 per night
Condo · Winter Park
Ski-In Ski-Out Studio with Desirable Amenities
Nov 6 – 13
$89 per night
Superhost
Condo · Winter Park
Winter Park Resort Condo walk to the base from your condo 3227
Oct 25 – Nov 1
$97 per night
Superhost
Condo · Winter Park
Riverfront Condo☆1st Floor☆Ski Bus☆Pool & Hot Tub
Jun 7 – 14
$117 per night
Superhost
Loft · Winter Park
NEW! Ski-In/Ski-Out Studio at Winter Park Base!
Nov 12 – 19
$89 per night
Superhost
Condo · Winter Park
Cozy Condo
Oct 12 – 19
$64 per night
Condo · Winter Park
WINTER PARK DREAM CONDO UNIT #16
Nov 5 – 12
$98 per night
Superhost
Condo · Winter Park
Top Floor with Beautiful Views! Larger 1-Bedroom!
Oct 16 – 23
$85 per night
Superhost
Condo · Winter Park
Winter Park 2bd/2ba (Sleeps 6) - Ideal Location!
Nov 13 – 20
$96 per night
Condo · Fraser
Cozy River View Studio Near WinterPark Ski Resort
Dec 8 – 15
$79 per night
Superhost

Winter Park summer home rentals

Home · Winter Park
Downtown Mountain Cabin
Oct 29 – Nov 5
$250 per night
Home · Winter Park
New Modern Cabin - Walk to Town/Shuttle Mins to WP
Nov 23 – 30
$455 per night
Superhost
Home · Winter Park
5BR Mountain Retreat, Sleeps 14, Hot Tub, 5 Acres
Apr 8 – 15
$563 per night
Superhost
Home · Tabernash
Modern Tabernash Retreat Private Hot Tub & Sauna
Jul 4 – 11
$252 per night
Superhost
Home · Fraser
Gorgeous, modern house with patio, fireplace, private hot tub, & mountain views!
May 13 – 20
$208 per night
Home · Fraser
Winter Park Area Family Cabin w/ Mtn View, Hot Tub
Aug 15 – 22
$431 per night
Home · Fraser
Quiet Fraser Family Escape: Hot Tub & Front Porch!
May 16 – 23
$267 per night
Superhost
Home · Granby
Wildhorse Chalet at Grand Elk - With Hot Tub!
May 1 – 8
$460 per night
Superhost
Home · Fraser
Evolve | Private Fraser House w/ Mtn Views & Grill
Dec 6 – 13
$243 per night
Home · Fraser
Family home with all the amenities, private hot tub, fire pit
Feb 9 – 16
$414 per night
Superhost
Home · Granby
Luxury Getaway in Winter Park
Aug 10 – 17
$362 per night
Home · Winter Park
Beautiful Rustic Home, Private, Close!
Sep 14 – 21
$523 per night
Superhost

Your guide to Winter Park

Introduction

This small mountain town consistently earns high praise from winter sports enthusiasts for its more than 3,000 acres of well-groomed slopes and powder stashes spread over seven separate ski areas. Its location in the Rocky Mountains positions it for more than 300 inches of prime powder each year; the runs are designed for skiers of all levels, making Winter Park the perfect place to go with the whole family or a group of friends. Even if skiing isn’t at the top of your list, other winter activities like snowshoeing, tubing, and snowcat tours provide plenty of options. Plus a new scenic gondola lets you take in the panoramic views.


When is the best time to stay in a vacation rental in Winter Park?

Winter Park shines during the snowy season. Skiing usually starts at the beginning of November, and the slopes can stay open until mid-April. The coldest month is January, with an average high temperature of 42 degrees Fahrenheit. The best time to visit is in March and early April, when some of the last, but best, snow drifts in and the days are sunnier and warmer (dependably in the mid-40s). Late spring is humid and chilly, and rain turns the snow to slush. The warmest month is July, when temperatures can reach 80 degrees. Fall is a splendid time of year to visit, thanks to brilliant red and yellow foliage, pleasant weather, and fewer crowds.


What are the top things to do in Winter Park?

Winter Park Resort

Winter Park Resort is the ideal basecamp for adventure, and features a wide range of activities year-round. There are many ways to experience the great outdoors here. A tubing park and bumper car course are popular with kids, while Nordic skiing and snowshoeing provide a slower-paced experience. When you’re through breaking a sweat, there are more than a dozen shops and restaurants to visit.

Winter Park Gondola

The Winter Park Gondola is the easiest and fastest way to access views of the Colorado Rockies in any season, whisking you to 11,000 feet elevation. The ride up offers a bird’s-eye view of ski runs and tree canopies. At the summit, you’re greeted by panoramic views of the Continental Divide and Fraser Valley, as well as access to hiking trails, lookouts, and a variety of ski runs.

James Peak Wilderness

Less than an hour’s drive from Winter Park is one of Colorado’s most impressive and underrated landscapes. James Peak Wilderness is located on the eastern side of the Continental Divide, and encompasses 17,000 acres. More than 20 miles of trails and streams meander through this alpine and subalpine ecosystem, including stands of willow, spruce, and Douglas firs.

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