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 226 properties available
This Winter Park family getaway offers a spacious and wonderful 2-bedroom accommodation. Situated on the ground floor of building 2, it provides convenient access to the free town shuttle and main clubhouse.This unit has undergone an amazing renovation, featuring hardwood flooring throughout the main open floor plan that perfectly complements the
Beaver Village Unit #0211
Condo -
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 24
This one of a kind luxury home rental offers 3 bedrooms and 3 bathrooms in a multi-level dwelling with outstanding furnishings and touch of high end fashion to make your Grand Lake vacation a dream come true and is Pet friendly!A spacious floor-plan makes the main living level a perfect place to enjoy time together. The main living room has vaulted
874 Kinnikinnick Rd
Private Vacation Home - Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 10 guests
Rating 5 10
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
Beaver Village Unit #1123
Condo -
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 11
Welcome to our condo at Iron Horse Unit D3074.A lovely and cozy studio condo with direct access to the slopes of Winter Park Resort, private balcony and modern interior design make for a relaxing vacation anytime of the year for a small family or couple.The open floor plan encompasses living, dining, sleeping and kitchen areas with newly installed
Iron Horse Building D Unit 3074
Condo -
Bathrooms 1 baths
Guests 4 guests
Rating 5 4
Welcome to our condo at Founders Pointe unit 4646.This luxurious and newly renovated 1 bedroom is situated on the top floor of the Founder's Pointe building and offers breathtaking mountain views from the private deck. This spacious unit comfortably accommodates up to 4 adults, providing all the comforts and conveniences of home. Unwind with family
Founders Pointe 4646
Condo -
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 4.9 12
This contemporary, pet friendly two-bedroom, two-bathroom condominium situated in the Reserve at Ten Mile Creek Apartments, boasts stunning mountain views from the private deck. It also provides easy access to a range of outdoor activities in the nearby region and at Granby Ranch Resort. The unit boasts a generous open floor plan, a chef-inspired
Hot HOT 14
Ten Mile G-201
Condo - Pet Friendly
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 24
This property offers an excellent setting for a small family or a couple seeking to experience downtown Winter Park, along with convenient access to local attractions. The updated one bedroom unit is located on the second floor, featuring a shuttle stop directly outside and a recreation building adjacent to the unit. The kitchenette is equipped wit
Hi Country Haus Unit 0309
Condo -
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 4.8 47
The living room features a leather sofa and armchair, providing a cozy area to relax by the gas fireplace, watch the flat screen television, and appreciate the private deck that overlooks a forested landscape from the building’s second floor, although it does not include air conditioning.The condominium is well-maintained boasting a modern kitchen
Hot HOT 10
Beaver Village Unit #0724R
Condo -
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 6 guests
Rating 4.7 13
This elegant slopeside mountain sanctuary with a private hot tub is an easy 5-minute walk to the Winter Park Resort. The Ski Haus is an exquisitely designed residence that captures the artistic and refined elements sought for your upcoming mountain retreat. With 6 bedrooms and 6 ½ bathrooms, it accommodates up to 19 guests, ensuring a comfortable a
Hot HOT 41
Winter Park Ski Haus
Private Vacation Home - Pet Friendly
Bedrooms 6 bedrooms
Bathrooms 6 baths
Guests 19 guests
Rating 5 62
This vacation rental in Winter Park, Colorado is conveniently situated within walking distance of the town and just a few minutes away from Winter Park Resort. This lovely 2-bedroom 2-bathroom unit at Beaver Village offers all the comforts of home and is located on the 2nd floor of the building.Visitors can take pleasure in the spacious open livin
Beaver Village Unit #0823
Condo -
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.9 33
Experience your next Winter Park retreat in this newly updated two-bedroom condo, situated on the second floor of the building. As an end unit, it features an extra window adjacent to the dining area, allowing you to appreciate the beautiful forest views.The unit boasts a vibrant and contemporary interior design and furnishings. The living room is
Beaver Village Unit #0324
Condo -
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 4.9 27
Kings Crossing 12 invites you to its unloading area at the entrance, which offers ample space for storing coats and boots. The indoor hot tub, conveniently located near the front door, provides a perfect way to unwind after a day of activities. This family-friendly townhome boasts an ideal location in downtown Winter Park close to a selection of re
Hot HOT 10
Kings Crossing Townhome 12
Townhome -
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 31

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