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.



Properties Available 238 properties available
The bedroom in this one bathroom condo features a Queen bed and a flat screen TV, along with an attached bathroom that has been recently renovated with a new dual vanity and tub/shower combination. An additional sleeping area is available in the main living room on the sofa sleeper. Please note that there is no air conditioning in this unit.The k
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.


Beaver Village Unit #0221R
Condo -
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 5 1
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
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 C Unit 3404
Condo -
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 5
The wonderfully modern and spacious home is the ideal spot for you and your family to enjoy plenty of views and year round mountain adventures. The tri-level floor plan offers 2 living spaces, 2 car garage, additional driveway parking, private deck, 3 bedrooms, 4 bedrooms and 4 ½ bathrooms - each bedroom has its own bathroom plus an office area wi
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.


892 Saddle Ridge
Private Vacation Home
Bedrooms 5 bedrooms
Bathrooms 5 baths
Guests 11 guests
This residence is ideally suited for several families or small groups seeking both privacy and a convenient location for their skiing or summer holiday. Notable features of this Winter Park home include stunning mountain views of the Continental Divide and Byers Peak, along with the added benefit of three master suites for enhanced privacy. We bel
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.


Leland Creek Home
Private Vacation Home -
Bedrooms 5 bedrooms
Bathrooms 4 baths
Guests 13 guests
Rating 4.5 16
Experience your next Winter Park retreat in this newly updated two-bedroom condo, situated on the second floor of the building. As an end unit, it features an extra window adjacent to the dining area, allowing you to appreciate the beautiful forest views.The unit boasts a vibrant and contemporary interior design and furnishings. The living room is
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.


Beaver Village Unit #0324
Condo -
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 8 guests
Rating 4.9 11
This timeless condominium is situated at the Iron Horse Resort, providing direct access to the slopes of the Winter Park Resort. It features two bedrooms and three bathrooms, accommodating up to eight guests.The kitchen and dining area are situated next to one another, featuring granite countertops, a dining table, tiled flooring and modern applia
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.


Iron Horse Building J Unit 1309
Condo -
Bedrooms 2 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 4.8 16
This two bedroom unit at Trailhead Lodge is ideal for a winter or summer retreat in the Colorado Rocky Mountains. Gather your family and furry friend for a luxurious yet approachable escape.The unit located on the second floor can be reached by elevator and features a tastefully decorated living room with expansive windows that provide scenic view
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.


Trailhead Lodges 422
Condo - Pet Friendly
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.9 72
This vacation rental boasts modern enhancements in the kitchen, including new cabinetry and fixtures, as well as a dining room adorned with a creatively designed picnic style table. The living room is characterized by exotic jewel tones on the walls, complemented by furnishings and accessories in similarly warm rich hues. Guests can take pleasure i
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.


Beaver Village Unit #1113
Condo -
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.7 4
This remodeled two-bedroom strikes an ideal balance between mountain charm and contemporary comfort, featuring an extensively renovated ground-floor corner unit situated. Located within the established Hi Country Haus community, it is just moments away from Main Street and clubhouse amenities, providing the best of both summer and winter living rig
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.


Hi Country Haus Unit 0701
Condo
Bedrooms 2 bedrooms
Bathrooms 1 baths
Guests 6 guests
A cozy sectional sofa serves as an ideal place to unwind after a day of exploring the beautiful outdoors of Winter Park. The living area is enhanced by a gas fireplace and a flat screen television, while the private deck on the second floor offers a serene view of the surrounding forest. The spacious renovated kitchen features modern appliances, n
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.


Beaver Village Unit #0821
Condo -
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.9 62
This charming, renovated kitchen features brand new stainless steel appliances complimented by sleek black tiled countertops, and elegant pine wood cabinets. The spacious living area in this inviting Fraser condominium boasts a modern flat screen HDTV mounted above the traditional wood burning fireplace, along with a DVD player and complimentary Wi
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.


Meadow Ridge Court 8 Unit 6
Condo -
Bedrooms 2 bedrooms
Bathrooms 1 baths
Guests 6 guests
Rating 4.6 19
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 37

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