StayWinterPark Labor Day vacation rentals

Celebrate Labor Day in Winter Park, Colorado

Book your mountain Labor Day getaway today - the last of the long summer weekends!

Plenty of great activities - free live music on Thursday 8/29 and 2 evenings at Cooper Creek Square.

Many restaurants have happy hour deals and dining specials.

Book one of our downtown rentals within walking distance of events or choose something a bit remote for peace and quiet!

Can't make it for the Labor Day weekend? Check out our more flexible vacation options.



Properties Available 164 properties available
Spacious 3-Bedroom Condo in Winter Park – Ideal Mountain RetreatWelcome to your perfect mountain getaway! This beautifully updated ground-floor condominiumoffers the comfort and convenience you need to make the most of your stay in Winter Park. Featuringthree spacious bedrooms and three full bathrooms, this 1,200-square-foot unit provides amp
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 B Unit 101
Condos -
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 9 guests
Rating 5 (1)
The newly installed carpeting and contemporary furnishings will enhance your retreat; this family friendly condominium provides an excellent location for your year-round Winter Park escape.Situated on the ground level of the building, this unit features a private deck that offers a serene forest view, perfect for unwinding with a morning coffee or
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 #1714
Downtown Winter Park -
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 4.8 (17)
This expansive and recently updated unit provides an excellent location for a mountain retreat at the foot of the slopes at Granby Ranch.  The primary living area features vaulted ceilings, inviting sofas perfect for relaxation, a gas fireplace, flat screen television and stunning mountain vistas through the large windows from this second floo
Hot HOT 16
Mountainside Unit B-20
Condos -
Bedrooms 2 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 (6)
This one bedroom condo has a mountain theme accents with personal touches making for a perfect spot to rent for families or a couples.The solid hardwood flooring in the dining room which will seat 4 to 6 people comfortably, for additional seating try using the kitchen counter that doubles as an extra eating place.  The kitchen offers lots of c
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 #0521R
Downtown Winter Park -
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 4.8 (7)
The interior of this vacation rental is adorned with a calming color palette, complemented by contemporary mountain-style furnishings and decor throughout the renovated space. The kitchen is equipped with modern appliances, elegant countertops and light wood cabinetry, seamlessly connecting to the dining area, which boasts a spacious table with ben
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 #1824
Condos -
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (5)
Adventure awaits! We are thrilled to offer our cozy mountain retreat to you.  Our condo is ideally situated just a short 10-minute drive or shuttle ride away from winter skiing and surrounded by summer outdoor activities. Winter Park is a mere 6 miles away and easily accessible via the complimentary shuttle service for all your seasonal advent
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!


Waterside West A303
Condos -
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 4.8 (35)
The living room exudes a warm and inviting ambiance, enhanced by the luxurious leather sofa and furnishings.  You can relish the comfort of the gas fireplace, watch programs on the flat screen TV and take a quick escape to the private patio.Experience this renovated condominium featuring granite countertops in the kitchen, complemented by mode
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 #1612R
Condos -
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 4.6 (6)
The hardwood flooring enhances the elegance of the kitchen, which features new wood cabinets, stainless steel appliances and countertops that include a breakfast bar accommodating four individuals.  In the dining area, a spacious table can comfortably seat up to six people and is complemented by a large window that provides a scenic view. Situ
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 #1734R
Condos -
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 4 (2)
Recently renovated, this comfortable ground floor 1 apartment offers a perfect place to unwind.  The private patio, accessible from the main living room, offers a view of the Winter Park Resort and is just a short walk from the main clubhouse.The living room offers a comfortable sofa, a flat screen TV, a wood burning fireplace and is connected
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 4
Condos -
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 4.5 (6)
Experience the inviting and cozy open floor plan of this modern 2-bedroom unit that can accommodate up to 6 guests. Enjoy convenient proximity to Winter Park, Grand Lake and Rocky Mountain National Park. Nearby amenities include Safeway, Fraser tubing hill, mountain biking trails and various dining options. Additionally, there is a stocked fishing
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!


Waterside West E206
Condos -
Bedrooms 2 bedrooms
Bathrooms 3 baths
Guests 6 guests
Rating 5 (5)
This spacious and attractive residence provides breathtaking mountain vistas and an excellent rental option for tranquility, capable of accommodating 6 individuals and welcoming pets.The main level features an open floor plan that includes the living, dining, kitchen areas, along with a half bathroom.  The living room provides a cozy space to
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!


2002 Lupine Lane
Private Vacation Homes - Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 (14)
The condominium exudes a unique cozy ambiance that will be appreciated by all, offering the conveniences of home and a fully renovated interior!  An elegantly modernized kitchen boasts  new cabinets, appliances and countertops.  The dining space can easily accommodate up to 6 individuals and is seamlessly integrated into the open lay
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 #0922
Downtown Winter Park -
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 7 guests
Rating 4.7 (19)

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