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!

Search Other Popular Vacation Rental Categories:

Private Homes, Winter Park Cabins, Base Village & Ski in Ski Out Vacation Rentals, Condo Complexes in Winter Park, Luxury Properties

166 properties available

The beautiful furnishings in the main living room offer a great spot to relax, enjoy the gas fireplace, flat screen TV and access to the private patio. An updated dining area offers seating for 4 persons.In the remodeled kitchen hardwood flooring, granite counter tops, stainless steel appliances and wood cabinets with 2 spots for seating at the bre

HOT 10

Beaver Village Unit #0412R

A spacious 1,200 square feet, this unit is on the first floor and has a living room decorated in with a southwestern decor, gas fireplace, TV, VCR, a queen sofa sleeper, free Wi-Fi access and no air conditioning.Next to the living room is the dining area with large table and chair setting for 6 people. Guests can also access the private deck with m

Timber Run Dogwood Unit 2

Spacious one bedroom , two bath condo with a convenient downtown Winter Park location to attend events, dine, and catch the free town shuttle. Includes access to the Hi Country Haus Rec Center with indoor pool, hot tubs and coin laundry. Take in the sounds and sites of the nearby creek that meanders around the backside of the condo from the private

HOT 13

Hi Country Haus Unit 1803

A cabin themed getaway condo is perfect for families and more! This ground floor condo has a forest view and is only steps away from town or a short shuttle ride from the Winter Park Ski Resort. The main living area provides hardwood flooring throughout and super comfortable furnishings to enjoy a spot near the gas fireplace and wooded view from t

Beaver Village Unit #1514

A comfortable 3 bedroom unit is on the second floor of the building offers a total of 1,128 interior square feet.On the main entry level, the living room has a gas fireplace, flat screen TV, DVD and Blue Ray disk player, free in unit Wi-Fi access and a queen sofa sleeper in the living room. No air conditioning.Adjacent to this area, is the dining r

Lion's Gate Pines Unit 115

A great downtown location for a family or small group getaway to Winter Park. This 3 bedroom condo has been recently remodeled. The main living area offers a vaulted ceiling, hardwood flooring in the kitchen and dining area and new carpeting throughout the remainder of the unit. Located on the 3rd floor of the building, guests can enjoy a wonderf

HOT 18

Beaver Village Unit #0833

A western themed 2 bedroom unit on the third floor of the building providing a wonderful getaway but close to Main Street in downtown Winter Park. This unit is also an end unit for additional peace and quiet.The main living area has tiled flooring, furnished with log accented lamps, lush leather sofa and chair where guest can enjoy the flat screen

Hi Country Haus Unit 1515

A very spacious 1,085 square foot rental, this 2 bedroom 2 bathroom condo offers view, master suite and a great spot for families or small group.The open living room is part of the open floor plan and has been comfortably furnished, wood burning fireplace, 50" Flat screen Smart TV, queen sofa sleeper and access to the 38 ft long private deck overlo

HOT 14

Hi Country Haus Unit 2111

Rated 5 stars, guests will love this completely remodeled two bedroom condo!The vacation rental has a new kitchen with pendant lighting, bright cabinets, stainless steel appliances and granite counter tops. The open floor plan consists of a living room and dining room with table large enough to accommodate six. A plush couch and chair with fireplac

Beaver Village Unit #0721

A great spot for couples (and Pets) wanting to take a break and enjoy downtown Winter Park luxury accommodations in the Arrow Townhomes. This unit will sleep up to 10 people in this 3 bedroom unit and it offers the best views with a private hot tub amenity for your next Winter Park vacation.A private garage where 2 cars can be parked in tandem is

HOT 23

Arrow at Winter Park Unit 276

The charming ground floor end unit has been updated with tiled in-floor heat to keep you warm in the winter and enjoy the gas fireplace any time of the year. Guests may catch a glimpse of a moose or a fox walking outside through the patio sliding doors within the Beaver Village Condos complex. The full kitchen is open to the living and dining to s

Beaver Village Unit #0414

A comfortable 3 bedroom 2 bathroom unit on the first floor, this rental has 1,212 square feet of living space with a split level interior floor plan.A large open living room includes a flat screen TV, DVD,Blue Ray disk player, free in unit Wi-Fi access and queen sofa sleeper. No air conditioning.Overlooking the living room is the main dining area

Lion's Gate Pines Unit 104

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