Winter Park Luxury Vacation Rentals

Explore Luxury Lodging in Winter Park, CO

Looking to make unforgettable and enduring memories during your upcoming mountain getaway? Search no further, reserve one of our opulent Winter Park rentals today; providing guests with something extraordinary and distinctive that is bound to be unforgettable! Stay Winter Park is delighted to offer a splendid array of vacation homes, cabins,  townhomes, and condos that surpass your typical vacation rental with numerous additional touches and details to enhance your stay right from the beginning.

Our deluxe rentals are all recently built and showcase top-of-the-line appliances, granite countertops, private garages, flat screen HDTVs, and more! Many of these Winter Park rentals also boast their own private hot tub and a spacious deck with stunning mountain views. Some even feature large communal areas for group gatherings. Numerous properties are conveniently situated near local attractions and activities, while others are tucked away off the beaten path, providing guests with a sense of seclusion.

Moreover, several properties in this luxury collection are ideal for corporate or executive retreats, family reunions, or weddings in Winter Park. We offer customized quotes for groups to accommodate your travel and event requirements, along with recommendations for local vendors offering additional services. Don't hesitate to reach to our Group Reservations team today. We encourage you to secure a vacation of a lifetime at any of these luxurious properties, explore all the rentals in this collection, and prepare to embark on an unforgettable journey.


Properties Available 48 properties available
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
Specials Tag 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.


Timber Fox Building B Unit 2102
Condo -
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 5 34
Beautiful new construction Modern townhome with private hot tub and fire pit on large roof top deck in Winter Park! 3 bedroom 3 bathroom unit with a spacious common area and a flex space that can be used as a fourth bedroom/second living/office. Walking distance to concerts, restaurants, and shops. Private Hot Tub, fire pit and bbq grill island on
Specials Tag 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.


17 Ski Idlewild
Townhome -
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 10 guests
Rating 5 33
Explore our brand new exquisite 2-bedroom, 2-bathroom condominium located in the center of downtown Winter Park! This flawless residence showcases top-notch contemporary aesthetics and comes fully furnished, perfect for your own use or as a vacation rental. Conveniently located near the main street, this unit provides easy access to Winter Park's d
Specials Tag 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.


Arrow at Winter Park Unit 202
Condo -
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 63
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
Hot HOT 14
Timber Fox Building C Unit 3308
Condo -
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 1
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
Specials Tag 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.


Winter Park Ski Haus
Private Vacation Home - Pet Friendly
Bedrooms 6 bedrooms
Bathrooms 6 baths
Guests 19 guests
Rating 5 62
Why You’ll Love this Colorado Escape• Spacious 4 bedroom penthouse condo with western themed decor• Gas fireplace and custom designed wet bar• Large deck with forest and mountain views • Access to a heated indoor pool and hot tub; game room and workout facility • Professionally Managed by Stay Winter ParkThe CondoThis spacious penthouse condo offer
Hot HOT 10
Silverado II Unit 631
Condo
Bedrooms 4 bedrooms
Bathrooms 4 baths
Guests 8 guests
Welcome to Arrow 213, a stunning new condo nestled in the heart of Downtown Winter Park, Colorado. This modern retreat offers a perfect blend of comfort and style, making it an ideal getaway for families or groups of friends seeking adventure and relaxation in the mountains.This spacious 1-bedroom, 2-bathroom unit comfortably accommodates up to 6 g
Specials Tag 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.


Arrow At Winter Park Unit 213
Condo -
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 5 guests
Rating 5 65
Organize your escape to this splendid pet friendly vacation residence in Winter Park Colorado. This expansive home provides all the comforts and amenities essential for an ideal family holiday, featuring three bedrooms and 2,790 square feet of living space spread across three levels, all just minutes from Winter Park Resort. The primary level feat
Specials Tag 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.


12 Yukon Lane Townhome
Private Vacation Home - Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 4.9 83
Why You’ll Love this Colorado Escape• 3.0 miles to Winter Park Ski Resort and 0.1 miles to Downtown Winter Park• Private rooftop terrace featuring a hot tub and outdoor seating for stargazing• Cozy gas fireplace, high ceilings and expansive windows• Garage parking for one vehicle and a spacious lower-level mudroom for gear storage• Professionally M
Specials Tag 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.


Arrow at Winter Park Unit 248
Townhome -
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 10 guests
Rating 4.9 48
Welcome to our home at 500 North Lupine! This charming townhome in Fraser is perfect for pet owners and provides a serene rental experience while being close to a variety of outdoor activities year-round. Located at the Cabins of Porcupine Ridge, this spacious 3-bedroom unit can host up to 8 guests, featuring breathtaking views and an open floor pl
Specials Tag 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.


500 North Lupine
Private Vacation Home - Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 10 guests
Rating 4.9 142
Welcome to our home at Homer’s Hideaway - 71 Alder Brook! Step into the luxury of Homer’s Hideaway, a spacious and beautiful home that’s perfect for your next getaway. This pet-friendly retreat features a private outdoor hot tub on the patio, soaring vaulted ceilings, and convenient 2-car garage parking. With enough room to comfortably sleep 10 gue
Specials Tag 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.


71 Alder Brook Homer’s Hideaway
Private Vacation Home - Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 10 guests
Rating 4.9 65
Experience mountain living at its finest in this stylish and serene mountain modern townhome that is thoughtfully designed with luxurious finishes making this townhome the ideal vacation rental for comfort and convenience and for extra enjoyment hop in the outdoor hot tub!The ground floor entrance offers hardwood floors, easy access to the garage p
Specials Tag Special
New Featured Properties

Browse our selection of new properties to our program and save 15% off 2 nights or more on your stay with promo code NEWUNIT.

*Offer is valid on new online bookings for 2+ night staysCannot be combined with other offers. Other exclusions and restrictions may apply to select properties.


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.


374 Lake Trail
Townhome -
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 7

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