President's Day Holiday Rentals in Winter Park

Spend President's Weekend in Winter Park Colorado

Visit Winter Park for the holiday weekend or weekday getaway with your sweetheart!

Plenty of great outdoor activities, dining or evening activities or just relax in your cozy vacation rental next to the fire!

Can't make it for President's Day weekend? Check out our more flexible vacation options




There is never a bad time to visit Winter Park

Spring Break, Winter or Summer, all you have to do is give us a call! We have local reservationist are here to help you plan your trip to Winter Park Colorado. 


Properties Available 213 properties available
The kitchen is aesthetically pleasing and well-lit, featuring modern cabinetry, pendant lighting, new countertops, and stainless steel appliances, fully equipped for meal preparations. The adjoining dining area accommodates up to six individuals, with extra bench seating and spaces at the breakfast bar, allowing for a total of ten place settings.T
Hot HOT 14
Beaver Village Unit #0833
Condo -
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 9 guests
Rating 4.8 29
Book your next upcoming ski or summer getaway at our family friendly-oriented 3 bedroom condo with clubhouse amenities. Our beautifully renovated and roomy split-level condo offers a private deck that offers forest views. The primary floor of the condominium is designed for your enjoyment, featuring an open floor that includes the main living ro
Meadow Ridge Pines B-7 Court 42
Condo -
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 8
This charming pet-friendly 3-bedroom retreat offers a cozy getaway for up to 8 guests and easy access to downtown Fraser's breweries, restaurants and great year round outdoor activities. A single level condo featuring an open floor plan with a fully equipped kitchen, breakfast bar, dining area, and a comfortable living room with a gas fireplace and
448 Cranmer Unit 103
Condo - Pet Friendly
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 4.9 60
Experience a stay in this exquisite three bedroom private townhome, where you can relish being close to the center of the vibrant downtown area filled with numerous activities. This residence offers an abundance of features, including a generous floor plan that accommodates up to 6 guests and a private outdoor hot tub for your enjoyment.The main e
Hot HOT 15
Sawmill Station Unit 302
Townhome -
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 6 guests
Rating 4.7 7
Adventure awaits! We are thrilled to offer our cozy mountain retreat to you. Our condo is ideally situated just a short 10-minute drive or shuttle ride away from winter skiing and surrounded by summer outdoor activities. Winter Park is a mere 6 miles away and easily accessible via the complimentary shuttle service for all your seasonal adventures.
Hot HOT 11
Waterside West A303
Condo -
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 4.9 98
Situated in the charming town of Winter Park, this location offers the convenience of walking to summer music festivals and events. During the winter months, guests can utilize the complimentary town shuttle service that operates within the condominium complex, providing direct transportation to Winter Park Resort for skiing or snowboarding advent
Beaver Village Unit #1824R
Condo -
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 5 4
This exceptional vacation rental offers a true home-away-from-home experience, characterized by its unique lodge ambiance, featuring rich wooden elements and comfortable furnishings in the main living space. Guests can unwind while enjoying the flat screen TV and the warmth of the gas fireplace, creating an ideal setting for a snug evening. Addit
Hot HOT 15
Beaver Village Unit #1123
Condo -
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 8
Indulge in the serenity of a delightful cabin tucked away in the woods but conveniently close to town, providing modern conveniences for your next getaway. Revel in a peaceful escape and a stunning night sky filled with countless stars. This charming cabin comfortably accommodates up to 6 guests and is positioned on a generous acreage, just a quic
Hot HOT 12
383 County Road 508
Cabin -
Bedrooms 3 bedrooms
Bathrooms 1 baths
Guests 8 guests
Rating 4.9 63
This two bedroom unit at Trailhead Lodge is ideal for a winter or summer retreat in the Colorado Rocky Mountains. Gather your family and furry friend for a luxurious yet approachable escape.The unit located on the second floor can be reached by elevator and features a tastefully decorated living room with expansive windows that provide scenic view
Hot HOT 17
Trailhead Lodges 422
Condo - Pet Friendly
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.9 72
Experience the tranquility of a beautifully designed, newly built cabin nestled in the woods, yet conveniently located near town, offering contemporary amenities for your upcoming retreat. Enjoy a serene getaway complemented by breathtaking views of the night sky adorned with countless stars and the surrounding forest. This inviting cabin can comfo
Hot HOT 17
1585 Moose Run
Cabin - Pet Friendly
Bedrooms 2 bedrooms
Bathrooms 1 baths
Guests 5 guests
Rating 5 15
This charming and expansive townhome in Fraser provides stunning mountain vistas from its private deck and patio, along with two interior levels that create a serene rental experience. It is ideally positioned near a variety of outdoor activities available year round. Located within the Winterstar condominiums, this three-bedroom unit can host up
Hot HOT 15
Winterstar Building A #6
Condo - Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 4.6 3
Escape to the mountains at this splendid, newly constructed residence boasting unforgettable mountain and lake views with a high-end interior designed 5 bedroom home that will sleep up to 10. This extraordinary mountain home offers beatle-kill hardwood flooring on the main level, accented by hand-hewn wooded plank ceilings and custom cabinetry.On
128 GCR 4034
Private Vacation Home -
Bedrooms 5 bedrooms
Bathrooms 4 baths
Guests 10 guests
Rating 5 6

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