Winter Park Vacation Rentals

Winter Park Lodging Accommodations 

Experience all that Winter Park has to offer by booking your stay today! At StayWinterPark, we have a wide selection of vacation rentals suitable for groups of any size.  Whether you're traveling with a small group or a large one, we have the perfect accommodation for you.  No matter the time of year, we can assist you in finding the ideal place to stay during your Colorado vacation.

Popular Searches: Private Homes, Colorado Cabins,  Luxury Vacation RentalsPet Friendly RentalsDowntown Winter ParkCondo Complexes, Townhome rentalsWinter Park Base Village and Ski In Ski Out

Other popular options include Fraser, TabernashGranby  and Grand Lake.

Properties Available 263 properties available
Reserve your upcoming visit to Winter Park in this opulent two bedroom unit at Pine Tree Plaza. Situated on Main street in the heart of downtown, you will have convenient access to dining, shopping, nightlife, summer festivals and the complimentary town shuttle - our condominium is perfect for families or small groups looking to experience the are
303 Pinetree
Condo -
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 15
Welcome to our condo at Hi Country Haus Unit 2301.Book your next downtown Winter Park escape in our 2 bedroom condo - lovely decorated interior, ground floor with private patio, across the street from main clubhouse and ½ block to main street with plenty of shops, restaurants and activities for you and your family to enjoy. A generously sized and
Hot HOT 10
Hi Country Haus Unit 2301
Condo -
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 11
This beautifully remodeled unit spans 1,200 square feet and is located on the building’s first floor. It is important to mention that there are roughly 6 to 8 steps leading to the unit as the ground floor accommodates a one car garage.In the primary living space, there is access to a private balcony that offers mountain views. This area features
Hot HOT 11
Timber Run Evergreen Unit 8
Condo -
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 3
Welcome to our townhome at 106 Homestead Loop! This exceptional 3-bedroom townhome includes a private outdoor hot tub with a view of a charming aspen grove, as well as a private deck that presents stunning mountain vistas. It is the perfect selection for a getaway in the Winter Park/Fraser region, featuring a stylish and comfortable interior design
Hot HOT 10
106 Homestead Loop
Townhome -
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 10 guests
Rating 4.8 9
Welcome to our townhome at 15 Saddle Horn Way - Rendezvous! This recently completed townhome showcases a three-story interior, featuring two private decks and a single private patio with picturesque forest views. It provides one-car garage parking and designated spaces for a washer and dryer, allowing residents to take in the beautiful forest scene
Hot HOT 10
15 Saddle Horn Way - Rendezvous
Townhome -
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 6 guests
Rating 5 5
Why You’ll Love this Colorado Escape• Walk across the street to Downtown Winter Park dining and shopping at Cooper Creek Square• Private balcony with views of Winter Park Ski Resort and the Continental Divide• Sleeps 8 guest across two bedrooms and a loft with three full bathrooms• Family accommodations include a provided Pack and Play, a game tabl
Hot HOT 13
Crestview Place Unit 607
Condo -
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 4.9 56
Welcome to our home at 1000 Lupine Lane.Our modern retreat provides a centralized location for easy access to the many activities in Winter Park, Granby Ranch, Snow Mountain Ranch and Grand Lake. Perfect for families or 2-3 couples with 3,000 square feet of interior living space encompassing 2 interior levels, 4 bedrooms to comfortably sleep up to
Hot HOT 12
1000 Lupine Lane
Private Vacation Home
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
Trailhead 821 is an excellent destination for families and is pet friendly, offering a sledding hill suitable for all ages, as well as fire pits for warming up at the Rendezvous Event Center. In the summer, visitors can enjoy the skate park and outdoor gymnasium. The property is conveniently accessible via the free town shuttle, making it an idea
Trailhead Lodges 821
Condo - Pet Friendly
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 4.9 132
The living room features a fireplace that is ideal for chilly evenings in both summer and winter. Take a look at the collection of books in the owner’s library, neatly arranged along the wall, perfect for days when you feel like staying indoors and reading a book or watching a movie on the flat screen TV. Guests also have access to the private pat
Beaver Village Unit #0711R
Condo -
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 4.9 57
Explore our brand new exquisite 2-bedroom, 2-bathroom condominium located in the center of downtown Winter Park! This flawless residence showcases top-notch contemporary aesthetics and comes fully furnished, perfect for your own use or as a vacation rental. Conveniently located near the main street, this unit provides easy access to Winter Park's d
Hot HOT 12
Arrow at Winter Park Unit 202
Condo -
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 63
Welcome to our hotel room at Winter Park Lodge II Unit E102! Experience a delightful stay in Fraser at this beautifully renovated hotel room featuring hardwood floors, full bathroom, flat screen television, mini-fridge, microwave, coffee making an small dining table and 2 chairs.Guests can enjoy access to an outdoor pool and hot tub as well as part
Hot HOT 10
Winter Park Lodge II Unit E102M
Fraser -
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 2 guests
Rating 5 1
The condominium is well-maintained boasting a modern kitchen equipped with new appliances, cabinets and countertops. The dining space features an elegant wooden table complemented by comfortable cushioned chairs, accommodating up to six individuals. An added perk of the dining area is the extra side window, allowing ample natural light to filter
Hot HOT 11
Beaver Village Unit #0724
Condo -
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.8 25

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