Stage 1 Fire Restrictions in place

StayWinterPark condo living room

StayWinterPark fall in downtown Winter Park

StayWinterPark family fall hiking

StayWinterPark breakfast bar in private home

StayWinterPark fall mountain and meadow view

StayWinterPark winter view of Continental Divide

Welcome to Winter Park...

Winter Park Lodging with Stay Winter Park

Book today to experience all Winter Park has to offer

StayWinterPark is the proud to have been voted the Best of Grand 2024 for Vacation Rental property management companies!

StayWinterPark is the top choice for the finest lodging deals in Winter Park Colorado when you choose to Book Local and Book Direct. Our dedicated team is prepared to provide assistance and curate a tailored experience for your Winter Park CO retreat. With a range of lodging options available, we can cater to your Colorado Vacation needs!

Our diverse selection of vacation rentals ensures there is something for everyone - whether you prefer mountain cabins, condos or townhomes with various amenities and features such as Ski-in/Ski-out condos, pet friendly accommodations or luxury vacation homes!

All our rentals grant convenient access to the fantastic outdoor activities in the region. Browse through our extensive collection online or contact our sales team to personalize your vacation experience according to your preferences and style. Begin planning your trip today and discover our top accommodations.

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New Properties

New Properties

StayWinterPark is always adding new rental properties to our profile for short term rentals.

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Find Your Winter Park Rental

Find Your Winter Park Rental

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Seasonal Activities

Seasonal Activities

Find the perfect activity based on the season!

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Lodging Specials

Lodging Specials

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Our Featured Vacation Rentals

View some of our Featured Properties selected just for you!

Featured Property Meadow Ridge Court 20 Unit 13

Meadow Ridge Court 20 Unit 13

2 bedrooms

2 baths

5 guests

Featured Property Townhome on Vasquez Creek #8

Townhome on Vasquez Creek #8

3 bedrooms

4 baths

13 guests

Featured Property Waterside West E206

Waterside West E206

2 bedrooms

3 baths

6 guests

Featured Property Summit Unit 1103

Summit Unit 1103

2 bedrooms

2 baths

5 guests

Featured Property Timber Fox Building C Unit 3406

Timber Fox Building C Unit 3406

2 bedrooms

2 baths

8 guests

Featured Property 206 Juniper

206 Juniper

6 bedrooms

4 baths

14 guests

Featured Property Cozens Pointe Building G Unit 202

Cozens Pointe Building G Unit 202

2 bedrooms

2 baths

6 guests

Featured Property Timber Ridge Building 3, Unit B

Timber Ridge Building 3, Unit B

3 bedrooms

3 baths

8 guests

Featured Property 2665 Golden Edge Drive

2665 Golden Edge Drive

4 bedrooms

3 baths

14 guests

Featured Property Elk Creek Condos B103

Elk Creek Condos B103

3 bedrooms

3 baths

10 guests

Featured Property Hi Country Haus Unit 2405

Hi Country Haus Unit 2405

1 bedrooms

2 baths

2 guests

Featured Property Beaver Village Unit #0713

Beaver Village Unit #0713

2 bedrooms

2 baths

6 guests

Featured Property 273 Fallen Rock

273 Fallen Rock

4 bedrooms

3 baths

11 guests

Recent Client Testimonials

Hear what some of our clients have said about us

We recently did a trip to Winterpark and stayed at Trailhead Lodge. Had an absolutely wonderful time. The booking and entire process through Stay Winter Park couldn't have been easier. Great communication and a wonderful place. Thanks for a great weekend!

Brian

Great company! So many amazing place to pick from! Easy communication, always clean rentals.

Samantha

Outstanding customer service is extremely rare these days but not at ‘Stay Winter Park.’ We first rented a place that wasn’t quite the right fit but after speaking with Shannon at ‘Stay Winter Park’, she gladly found us a perfect fit. They will forever have our business on our Winter Park vacations!

The house was immaculate, very nicely decorated and had all the amenities anyone could ever even think they needed. The neighborhood is nice and quiet and just a short drive or walk to many restaurants and local shopping.

Chris

Communication was easy and detailed. Prices were great and condo was wall stocked and was just as described in online. Stay Winter Park was easy to work with and we would for sure rent from them again!

Kevin

Can't say enough good things! Highly recommend this condo for a relaxing vacation for families or couples. Ideally situated close to both downtown Winter Park and massive trail system - the best of both worlds. Very comfortable place to stay and use as a home base for adventures. Also Beaver Village clubhouse has a great pool and hot tub. Outstanding customer service that makes the guest experience easy. Whether you like hiking, biking, skiing, walks along the river, or simply coffee and a book with mountain sun and fresh air, this is a can't miss spot.

Joanna

Can not recommend this place enough. Stayed here with another family, 8 of us total, and did not feel cramped! Plenty of room, board games for kids and everything needed in the kitchen. PERFECT location to walk to restaurants, shops and Recreation center. We all enjoyed the pool table and multiple hot tubs available at the rec center as well as the pool. The hosts were prompt with anything that came up and would HIGHLY recommend to anyone wanting to visit the Winter Park area. We loved the accessibility to the many trails (even in the backyard), the Playground/Skate park (which is downtown) and being able to access Rocky Mountain National Park on the west side. Can’t imagine how beautiful this place would be in the Winter and would love to come back.

Julia

This unit was better than anticipated. Very spacious and well stocked. Mountain Views from porch, primary bedroom and den. The management was very communicative and friendly. We’d definitely stay here again.

Sheree

We had a lovely stay. The place is amazingly gorgeous. Went beyond my expectations. I highly recommend to stay here. The hosts are super friendly and very proactive. Everything went smoothly.

Alex