Downtown Winter Park

Vacation Rentals in Downtown Winter Park CO

Downtown Winter Park is a great hub of restaurants, shops and year-round activities that you can explore while staying in your Winter Park Vacation Rental. You can stay right on Main Street or within 1 block for easy access to all that is happening in Downtown Winter Park! 

Stay Winter Park offers a large variety of rentals ranging from condos to luxury townhomes. During the summer months, enjoy the music festivals at Rendezvous Event Center, art festivals and outdoor dining with live free music and easy access to a number of hiking and mountain biking trails. For the winter months, you can still enjoy the local dining, sledding hill and the free town shuttle can provide transportation to the ski resort or the town of Fraser.

Can't wait to book your getaway? Browse our inventory of downtown Winter Park vacation rentals below and book online with our easy reservation system. Please contact our sales team with any questions or for special requests to help make your vacation unforgettable!


Properties Available 168 properties available
This Trailhead Lodge 2 bedroom unit is great for either a winter or summer getaway to the Colorado Rocky Mountains - grab the family and fido for a luxurious getaway with a down to earth feel.The second floor unit is accessible via elevator and offers a beautifully furnished living room with large windows for views, spot to relax and enjoy the gas
Trailhead Lodges 422
Condo - Pet Friendly
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.8 23
A comfortable, two story townhome rental offers a comfortable open floor plan in the living room with TV, VCR, wood burning fireplace, queen sofa sleeper and has access to the small private patio. Adjacent to the living room is the dining area with table and chairs to seat 6 persons. Upgrades in the kitchen include new counter tops and appliances
Hideaway Village Alpine 4
Townhome -
Bedrooms 4 bedrooms
Bathrooms 2 baths
Guests 4 guests
Rating 5 2
Rich leather sofa and wood furnishings complete the warm and inviting atmosphere in the living room where you can enjoy the gas fireplace, flat screen TV and a quick escape to the private patio.Enjoy this remodeled condo with granite counter tops in the kitchen as well as newer appliances, hardwood flooring and cabinets. A small island offers a sp
Beaver Village Unit #1612R
Condo -
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 4 1
Beautiful and spacious pet friendly 3 bedroom unit right from the heart of downtown Winter Park, this Trailhead Lodge unit has a wonderful view off the back deck of the Winter Park Ski Resort and downtown area of Winter Park a great place to drink morning coffee, outdoor dining area or a great spot to enjoy the evening sunsets.Families or small gro
Trailhead Lodges 131
Condo - Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 9 guests
Rating 5 22
This one bedroom condo has all you need for your vacation. The master bedroom has a queen bed, flat screen TV and en-suite full bathroom. A full kitchen is complete with cookware and updated appliances, cabinets and counter tops. A small island has a spot for 2 to seat and is open to the dining room with additional seating for 4. In the living s
Beaver Village Unit #1633R
Condo -
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 5 1
Walk into a wonderfully modern and remodeled 3 bedroom unit! On the ground floor of the building allowing for easy access in and out, there is hardwood flooring throughout the main living area.As soon as you walk into the unit, the kitchen beautifully remodeled with new appliances, granite counter tops, wood cabinets and breakfast bar with seating
Hot HOT 11
Hi Country Haus Unit 1801
Condo -
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 4.6 12
Tons of light and a lot of square footage in this tri-level town home make it the ideal vacation rental for families or singles looking for lodging that has a lot of space. The main level has a large entryway with tiled flooring to storage your jackets, coats and an excellent spot to access the one car garage, laundry room and bedroom with 2 twin b
Hot HOT 11
Timber Lake 341
Townhome -
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 4.8 9
In the main living room of the unit, large comfortable furnishings compliment a wood paneled accent wall, TV, VCR/DVD, gas fireplace, free in unit Wi-Fi access, queen sofa sleeper and no air conditioning. The dining area provides guests access the private balcony with wonderful mountain views and the large table offers seating for 8 persons.A full
Timber Run Cedar Unit 3
Condo
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
A comfortable, remodeled condo with views of the Fraser River making it a wonderful rental for guests wanting to relax and enjoy Winter Park.Beautiful hardwood flooring throughout the unit compliment the modern theme and new furnishings. In the living room, a new flat screen TV, VCR, DVD, wood fireplace and queen sofa sleeper. The fully equipped
Hi Country Haus Unit 1503
Condo -
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 4.8 17
Lavish interior decor and some of the high-end finishes that afford a luxury getaway at these Telemark townhomes. All units come complete with the common features of four-panel interior alder doors and trim, pendant styled lighting and energy efficient radiant heating system. A wonderful location in downtown Winter Park close to all the activities,
Telemark Townhomes Unit 514
Condo - Pet Friendly
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 4.8 24
This 1,292 square foot unit has two interior levels for a comfortable 3 bedroom rental.In the main living room an open floor plan has comfortable furnishings, gas fireplace, flat screen TV with DVD and Blue Ray disk player, in unit Wi-Fi access and a queen sofa sleeper. No air conditioning.Adjacent to the kitchen, the dining area has seating for 8
Lion's Gate Pines Unit 101
Condo
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
New carpeting throughout and a modern theme for furnishings will compliment your getaway - this family friendly condo offers a wonderful spot for your Winter Park getaway year round. Located on the ground floor of the building with private deck with a forest view to relax and enjoy a cup of coffee in the mornings or a peace evening after enjoying a
Beaver Village Unit #1714
Condo -
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.8 13

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