StayWinterPark Memorial Day Getaway

Book your Memorial Day lodging today!

The kick-off for the summer season is finally here. 

Gather the family and head to the mountains to honor and celebrate those who gave the ultimate sacrifice. When you come to the Colorado Rockies, you will experience the fresh mountain air, the sights and sounds of nature, and some of the best cuisine Winter Park, Colorado, has to offer. 

So many vacation rentals to pick from in Winter Park - use our quick links below to book a great holiday weekend - condos, cabins or private homes.  Check out pet friendly rentals too!

All our rentals are close to the great outdoors and provide the perfect spot to relax and enjoy!

Enjoy local events to enjoy during your vacation.

  • The Jane Beach – May 10, 17, and 24, 2025

Can't make it for Memorial Day? Check out our more flexible vacation options




Properties Available 148 properties available
This recently renovated 2-bedroom condo provides a cozy and updated accommodation choice in Fraser.  The spacious living room features plush sofas encircling a gas fireplace, a large flat screen TV, and access to a private balcony with views of the Winter Park Ski Resort. The unit also boasts new hardwood flooring throughout.The dining area ne
Specials Tag Special
May lodging deals

Spring is finally here and summer is just around the corner!

Book your lodging direct with StayWinterPark and save on your lodging - we've made it easy - no promo or booking codes needed for the best price!

You can also book for your next summer adventure!

This offer is valid for new reservations only and cannot be combined with any other offers.  Valid dates of stay are 5/1/2025-9/30/2025.  All reservations must be booked by 5/31/25. 

Call us at 1-800-215-6535book online, or email us at info@staywinterpark.com to book your Winter Park Getaway!


Meadow Ridge Court 18 Unit 11
Condos -
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.7 (4)
The condominium features a cozy interior, complete with modern flooring and new furnishings throughout the primary living space, making it an ideal location for your upcoming Winter Park mountain retreat in this charming three bedroom, three bathroom unit. The primary open floor plan features a living room equipped with a gas fireplace and a 5
Specials Tag Special
May lodging deals

Spring is finally here and summer is just around the corner!

Book your lodging direct with StayWinterPark and save on your lodging - we've made it easy - no promo or booking codes needed for the best price!

You can also book for your next summer adventure!

This offer is valid for new reservations only and cannot be combined with any other offers.  Valid dates of stay are 5/1/2025-9/30/2025.  All reservations must be booked by 5/31/25. 

Call us at 1-800-215-6535book online, or email us at info@staywinterpark.com to book your Winter Park Getaway!


Silverado I Building C Unit 101
Condos -
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (12)
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 equippe
Specials Tag Special
May lodging deals

Spring is finally here and summer is just around the corner!

Book your lodging direct with StayWinterPark and save on your lodging - we've made it easy - no promo or booking codes needed for the best price!

You can also book for your next summer adventure!

This offer is valid for new reservations only and cannot be combined with any other offers.  Valid dates of stay are 5/1/2025-9/30/2025.  All reservations must be booked by 5/31/25. 

Call us at 1-800-215-6535book online, or email us at info@staywinterpark.com to book your Winter Park Getaway!


Hi Country Haus Unit 0309
Condos -
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 4.5 (11)
Experience one of the finest vistas in Winter Park at this Arrow townhome.  Spanning three levels, this tri-level residence is ideally situated on Main Street in downtown Winter Park, making it an excellent choice for your upcoming mountain getaway.  The townhome boasts a generous 1,436 square feet of living space across four levels, feat
Hot HOT 15
Arrow at Winter Park Unit 274
Townhome -
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 10 guests
Rating 4 (1)
The condominium is well-maintained boasting a modern kitchen equipped with new appliances, cabinets and countertops.  The dining space features an elegant wooden table complemented by comfortable cushioned chairs, accommodating up to six individuals.  An added perk of the dining area is the extra side window, allowing ample natural light
Specials Tag Special
May lodging deals

Spring is finally here and summer is just around the corner!

Book your lodging direct with StayWinterPark and save on your lodging - we've made it easy - no promo or booking codes needed for the best price!

You can also book for your next summer adventure!

This offer is valid for new reservations only and cannot be combined with any other offers.  Valid dates of stay are 5/1/2025-9/30/2025.  All reservations must be booked by 5/31/25. 

Call us at 1-800-215-6535book online, or email us at info@staywinterpark.com to book your Winter Park Getaway!


Beaver Village Unit #0724
Downtown Winter Park -
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.6 (9)
This recently renovated three-bedroom property includes an additional bunk room, allowing accommodation for up to nine guests.  The rooftop hot tub is an irresistible feature, making it the perfect choice for your next Winter Park vacation.  Additionally, this property is pet-friendly, ensuring a memorable downtown getaway for all. A
Specials Tag Special
May lodging deals

Spring is finally here and summer is just around the corner!

Book your lodging direct with StayWinterPark and save on your lodging - we've made it easy - no promo or booking codes needed for the best price!

You can also book for your next summer adventure!

This offer is valid for new reservations only and cannot be combined with any other offers.  Valid dates of stay are 5/1/2025-9/30/2025.  All reservations must be booked by 5/31/25. 

Call us at 1-800-215-6535book online, or email us at info@staywinterpark.com to book your Winter Park Getaway!


Arrow at Winter Park Unit 286
Townhome - Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 9 guests
Rating 4.8 (35)
This charming and expansive pet friendly three bedroom unit is located in the very center of downtown Winter Park.  The Trailhead Lodge unit offers a stunning view from the back deck overlooking the Winter Park Ski Resort and downtown area.  It serves as an excellent location for enjoying morning coffee, featuring an outdoor dining area a
Specials Tag Special
May lodging deals

Spring is finally here and summer is just around the corner!

Book your lodging direct with StayWinterPark and save on your lodging - we've made it easy - no promo or booking codes needed for the best price!

You can also book for your next summer adventure!

This offer is valid for new reservations only and cannot be combined with any other offers.  Valid dates of stay are 5/1/2025-9/30/2025.  All reservations must be booked by 5/31/25. 

Call us at 1-800-215-6535book online, or email us at info@staywinterpark.com to book your Winter Park Getaway!


Trailhead Lodges 131
Condos - Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 9 guests
Rating 5 (10)
Situated in the upper cul de sac of Beaver Village, this unit adjoins the forest, providing stunning views of the Winter Park Resort from the private balcony. The second floor is bathed in natural light, enhancing its appeal.  As an end unit, it offers a tranquil and secluded atmosphere. The renovated kitchen is equipped to facilitate bot
Specials Tag Special
May lodging deals

Spring is finally here and summer is just around the corner!

Book your lodging direct with StayWinterPark and save on your lodging - we've made it easy - no promo or booking codes needed for the best price!

You can also book for your next summer adventure!

This offer is valid for new reservations only and cannot be combined with any other offers.  Valid dates of stay are 5/1/2025-9/30/2025.  All reservations must be booked by 5/31/25. 

Call us at 1-800-215-6535book online, or email us at info@staywinterpark.com to book your Winter Park Getaway!


Beaver Village Unit #1624
Downtown Winter Park -
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.7 (11)
Exceptional Opportunity! This is a 4-bedroom, 3-bathroom residence in Beaver Village . If you seek convenience and comfort for your upcoming ski vacation in Winter Park, this is the ideal accommodation.This second-floor condominium offers the convenience of single-level living. Upon entering, you are greeted by hardwood flooring that leads into the
Specials Tag Special
May lodging deals

Spring is finally here and summer is just around the corner!

Book your lodging direct with StayWinterPark and save on your lodging - we've made it easy - no promo or booking codes needed for the best price!

You can also book for your next summer adventure!

This offer is valid for new reservations only and cannot be combined with any other offers.  Valid dates of stay are 5/1/2025-9/30/2025.  All reservations must be booked by 5/31/25. 

Call us at 1-800-215-6535book online, or email us at info@staywinterpark.com to book your Winter Park Getaway!


Beaver Village Unit #1124
Downtown Winter Park -
Bedrooms 4 bedrooms
Bathrooms 3 baths
Guests 10 guests
Rating 4.8 (18)
This well-appointed and recently renovated one bedroom one bathroom unit is conveniently situated near the town of Winter Park and is accessible via the complimentary town shuttle to Winter Park Resort.  The rental is equipped with all essential amenities for a pleasant vacation, including a fully equipped kitchen complete with dishware and co
Specials Tag Special
May lodging deals

Spring is finally here and summer is just around the corner!

Book your lodging direct with StayWinterPark and save on your lodging - we've made it easy - no promo or booking codes needed for the best price!

You can also book for your next summer adventure!

This offer is valid for new reservations only and cannot be combined with any other offers.  Valid dates of stay are 5/1/2025-9/30/2025.  All reservations must be booked by 5/31/25. 

Call us at 1-800-215-6535book online, or email us at info@staywinterpark.com to book your Winter Park Getaway!


Beaver Village Unit #0931R
Condos -
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 4 (1)
Visitors are guaranteed to appreciate the elegantly renovated kitchen, which features stainless steel appliances, granite countertops, newly installed hardwood flooring, and cabinetry, It  is fully equipped with cookware, dishes and utensils. allowing for the preparation of delightful meals throughout their stay.The presence of vaulted ceiling
Specials Tag Special
May lodging deals

Spring is finally here and summer is just around the corner!

Book your lodging direct with StayWinterPark and save on your lodging - we've made it easy - no promo or booking codes needed for the best price!

You can also book for your next summer adventure!

This offer is valid for new reservations only and cannot be combined with any other offers.  Valid dates of stay are 5/1/2025-9/30/2025.  All reservations must be booked by 5/31/25. 

Call us at 1-800-215-6535book online, or email us at info@staywinterpark.com to book your Winter Park Getaway!


Beaver Village Unit #2032
Condos -
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.8 (17)
Experience the tranquility of a beautifully designed, newly built cabin nestled in the woods, yet conveniently located near town, offering contemporary amenities for your upcoming retreat. Enjoy a serene getaway complemented by breathtaking views of the night sky adorned with countless stars and the surrounding forest. This inviting cabin can comfo
Specials Tag Special
Featured New Properties

StayWinterPark is expanding our rental inventory with new properties!

Check out the newest listings and book online today.

Use promo code new for 15% savings on your booking for 2 nights or more.

If you have specific questions or need personalize assistance with your booking, call us at 1-800-215-6535book online or email us at info@staywinterpark.com.

1585 Moose Run
Cabin -
Bedrooms 2 bedrooms
Bathrooms 1 baths
Guests 5 guests
Rating 5 (6)

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