Flexible Stays

Flexible Stays & Same Day Bookings

Book a last minute getaway to Winter Park Colorado. Search our vast selection of short term rentals located in Winter Park CO. Stay between 1 night to a week plus & enjoy same day booking when you book direct! Check out our new weekly discount rates - stay 5 nights or more for the best price!

Have your choice of Colorado Vacation Rentals in Winter Park from Cabins and Private Homes to Condos , Townhomes


Properties Available 215 properties available
Escape to Redroc Lodge, an exquisite 5-bedroom, 4-bathroom retreat in the captivating Winter Park Highlands of Tabernash. This 5,300-square-foot sanctuary seamlessly fuses rustic mountain charm with contemporary comforts, offering sweeping Rocky Mountain vistas. With a updated kitchen, inviting living areas, entertainment rooms, and a picturesque o
864 Rainbow The Redroc Lodge
Private Vacation Home -
Bedrooms 5 bedrooms
Bathrooms 4 baths
Guests 15 guests
Rating 5 1
This is a 2 bedroom 2 bathroom unit on the first floor of the building and has 1,200 interior square feet.In the living room guests will enjoy a gas fireplace, TV with VCR, modern comfortable furnishings and a queen sofa sleeper, free Wi-Fi access and no air conditioning.Adjacent to the living room, the dining area offers a solid wood table with ch
Timber Run Evergreen Unit 101
Condo
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Bright and inviting with spectacular views of the surrounding forest from the 2 private decks on the second floor of the building in this spacious 2 bedroom, 2 bath sleeping 6. It is located just minutes from downtown Winter Park and approximately 3 miles from the Winter Park Resort. The free lift shuttle bus service stops in front of the complex
Silverado II Unit 224
Condo -
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 3 1
An ultra-modern and beautifully appointed townhome has 1,764 square feet of living space on two levels and lots of large windows to marvel at the magnificent mountain views from this vacation rental. A spacious living room is south facing for spectacular sunsets, access to the private deck with BBQ grill, space to relax and the private hot tub. Al
Hot HOT 14
47 Lookout Point - Rendezvous
Private Vacation Home -
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 10 guests
Rating 5 8
A very spacious Fraser Colorado rental property with 2 bedroom loft 2 bathroom unit has 1, 119 square feet of living space, an end unit with 3 interior levels and is a non-smoking and no pets condo.The main living and dining rooms have new carpeting with comfortable furnishings that face the wood-burning fireplace, flat screen TV with VCR, DVD and
Hot HOT 10
Meadow Ridge Court 14 Unit 1
Condo -
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 9 guests
Rating 4.4 9
You will enjoy this beautifully updated kitchen with black granite counter tops, oak cabinetry and radiant in-floor heat is perfect for chilly mornings! in this 2 bedroom 2 bathroom condo rental.The dining area is adjacent to the kitchen and has a large table that will comfortably seat 6 people. In the living room, you can enjoy the large flat scr
Beaver Village Unit #0621
Condo -
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 1
This 2 bedroom, 2 bathroom condo is 950 square feet and has an open floor plan with newer carpeting throughout and the updated kitchen with stainless steel appliances. The condo is on the 3rd floor with no elevator access. The elevator only brings you from the parking level to the building level. A wonderfully bright and inviting condo offers spect
Hot HOT 15
Silverado II Unit 334
Condo -
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 4 guests
Rating 5 4
Located at the Trailhead Lodges complex and on the shuttle route this property is the ultimate ski retreat for a couple, small family or 2 singles seeking comfortable accommodations. This wonderful 1 bedroom is also conveniently located next to the Rendezvous Event Center with sledding hill fit for all ages and firepits warm up. Easy walk to main
Hot HOT 28
Trailhead Lodges 731
Condo -
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 4.9 34
Discover our new stunning 2-bedroom, 2-bathroom condo in the heart of downtown Winter Park! This immaculate unit features high-quality modern design and is offered fully furnished, ready for your enjoyment or as a vacation rental. Situated just off the main street, you'll have easy access to Winter Park's dining and entertainment. With 9-1/2 ft cei
Hot HOT 13
Arrow at Winter Park Unit 202
Condo -
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 2
A great location for a small family or a couple to enjoy downtown Winter Park and easy access to the area’s adventures. Second floor updated one bedroom with shuttle stop right out front and recreation building situated in the building next door. The kitchenette includes a mini-fridge, 4 burner stove with oven, microwave, dishwasher and dining area
Hi Country Haus Unit 0309
Condo -
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 4.6 6
This Winter Park condo has a lot of space and numerous bedding options for groups, families, couples and singles. This four bedroom three bathroom condo is one of our largest units at the Beaver Village Condominiums complex, located on the 3rd floor, the vaulted ceilings really add in a lot of light.Comfortable furnishings throughout the open floo
Hot HOT 19
Beaver Village Unit #0834
Condo -
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 10 guests
Rating 4.5 4
From the comfy living room couch enjoy the gas fireplace, flat screen TV which includes Blu-Ray, cable TV or the view from the sliding glass doors out to the private balcony. Step outside to use the gas grill and take in the secluded woods, with glimpses of wildlife and distant mountain views make this a choice location from the second floor of the
Hot HOT 16
Beaver Village Unit #0723
Condo -
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 2

Tell us what you're looking for and someone will contact you with available options.

By providing your phone number, you agree to receive text messages from our company. Message and data rates may apply. Message frequency varies.
I agree