Downtown Winter Park Rentals

Vacation Rentals in Downtown Winter Park CO

Downtown Winter Park boasts a vibrant array of restaurants, shops and year-round activities for guests staying in a Winter Park vacation rental. Whether you choose to stay on Main Street or within a block, you'll have convenient access to all that the excitement in Downtown Winter Park!

Stay Winter Park offers a diverse selection of rentals from condos to luxury townhomes. In the summer, guests can enjoy music festivals at Rendezvous Event Center, art festivals, outdoor dining with live music and easy access to hiking and mountain biking trails. During the winter months, visitors can still savor local dining, visit the sledding hill and utilize the free town shuttle for transportation to the ski resort or the town of Fraser.

Excited to plan your getaway? Explore our inventory of downtown Winter Park vacation rentals below and easily book online using our reservation system. For inquiries or special requests, please reach out to our sales team for assistance in creating an unforgettable vacation experience!

Search Other Popular Vacation Rental Categories:

Private Homes, Colorado Cabins, Pet Friendly Rentals, Winter Park Base Village , Ski-In, Ski-Out Condo Rentals, Condo Complexes, Luxury Vacation Rentals, Fraser, Tabernash, Granby, Grand Lake

144 properties available

Welcome to our condo at Hi Country Haus Unit 2301.Book your next downtown Winter Park escape in our 2 bedroom condo - lovely decorated interior, ground floor with private patio, across the street from main clubhouse and ½ block to main street with plenty of shops, restaurants and activities for you and your family to enjoy. A generously sized and

HOT 24

Hi Country Haus Unit 2301

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This tri-level townhome offers an abundance of natural light and generous square footage, making it the perfect vacation rental for families or individuals seeking spacious accommodations.The primary level features a spacious entryway adorned with tiled flooring, providing ample space for storing jackets and coats. This area also offers convenient

Special

Stay Longer in Winter Park, Save Bigger

Sink into vacation mode in the Fraser Valley and Winter Park area and enjoy 20% off 7–21 night stays with promo code LTR26. Travel between April 14 and December 18, 2026, and book by December 10, 2026, to lock in your savings.*

Looking for something beyond a three-week stay? We'll help you plan a longer stay that works for you, contact us at (800) 215-6535 or [email protected] to inquire about flexible options and best pricing.

*Offer is valid on new online bookings when you book by December 10, 2026, for length of stays between 7 and 21 days between April 14 and December 18, 2026. Cannot be combined with other offers. Exclusions and restrictions may apply to select properties.

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Why You’ll Love this Colorado Escape• 2 bedroom and 2 bathroom second floor end unit with enhanced privacy• Easy access to a private deck overlooking the forest• Complex clubhouse access featuring a heated indoor pool and hot tubs • Cozy gas fireplace and a fully remodeled kitchen with a small island • Professionally Managed by Stay Winter ParkThe

HOT 18

Beaver Village Unit #0624

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Welcome to our condo at Timber Fox Unit C3308! This newly constructed, luxurious three bedroom unit is situated in the vibrant center of downtown Winter Park. Our unit offers a splendid view from its private patio with outdoor sofa, open floor plan with a modern themed interior design, gourmet kitchen, washer and dryer and will sleep 8 guests comfo

Timber Fox Building C Unit 3308

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Welcome to your cozy mountain retreat at Timber Fox Building C Unit 3404, nestled in the heart of Winter Park. This luxurious 2-bedroom, 2-bathroom condo offers a perfect blend of comfort and elegance, ideal for families or groups of friends seeking a memorable getaway.Step inside to discover a thoughtfully designed living space, complete with a mo

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Timber Fox Building C Unit 3404

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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

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Hi Country Haus Unit 0309

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This expansive ground floor condominium features three bedrooms and three bathrooms, making it an ideal location for your mountain getaway, and has been updated for enhanced comfort. The living room boasts an open layout with newly installed hardwood flooring, a wood burning fireplace and a 50 inch flat screen HDTV, all of which can be appreciated

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Silverado I Building A Unit 101

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Hi Country Haus 503 is a 1 bedroom unit on the ground floor and provides a great spot for your Winter Park ski vacation.This unit has 492 square feet, non-smoking and no pets allowed unit. The living room has a flat screen TV with cable and wood burning fireplace. The couch in the living room has a queen sofa sleeper. The kitchenette has just been

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Hi Country Haus Unit 0503

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The exclusive terrace associated with the third floor unit in the building presents scenic views of the Winter Park Resort, serving as a tranquil area to appreciate the outdoors. It has recently undergone updates, making it an excellent choice for your upcoming Winter Park getaway. The open-concept layout includes a well-equipped kitchen, complete

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Beaver Village Unit #0931

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Trailhead 821 is an excellent destination for families and is pet friendly, offering a sledding hill suitable for all ages, as well as fire pits for warming up at the Rendezvous Event Center. In the summer, visitors can enjoy the skate park and outdoor gymnasium. The property is conveniently accessible via the free town shuttle, making it an idea

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Welcome to our townhome at Hideaway Village Lenado 4.Renovated unit with private patio and 2 private decks, forest and river views. This unit has tri-level interior and will sleep up to 6, on the free town shuttle and is located in a quiet Winter Park neighborhood and close to many outdoor hiking, biking, snowshoe and cross country trails. Ideal m

HOT 18

Hideaway Village Lenado 4

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This newly constructed, luxurious three bedroom unit is situated in the vibrant center of downtown Winter Park. The Timber Fox offers a splendid view from its private patio, overlooking the Winter Park Ski Resort and the adjacent forested landscape, making it an ideal location to unwind, savor morning coffee and utilize the BBQ grill.The primary o

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Timber Fox Building B Unit 2102

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