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Welcome to Winter Park...

Winter Park Lodging with Stay Winter Park

Book today to experience all Winter Park has to offer

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

Our diverse selection of Winter Park vacation rentals ensures there is something for everyone - whether you prefer cabin rentals in Colorado, Winter Park condo rentals or upscale townhomes with various amenities and features such as Ski-in/Ski-out condos, pet friendly accommodations or luxury Colorado 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 Winter Park vacation rental experience according to your preferences and style. Begin planning your Colorado trip today and discover our top Winter Park 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

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Seasonal Activities

Seasonal Activities

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Our Featured Vacation Rentals

View some of our Featured Properties selected just for you!

Featured Property 524 Sun River #8

524 Sun River #8

2 bedrooms

2 baths

6 guests

Featured Property Townhome on Vasquez Creek #6

Townhome on Vasquez Creek #6

4 bedrooms

4 baths

10 guests

Featured Property Spruce Ridge Unit H

Spruce Ridge Unit H

3 bedrooms

3 baths

8 guests

Featured Property Lance's Adventure Lodge

Lance's Adventure Lodge

4 bedrooms

3 baths

10 guests

Featured Property 492 Golf Course Circle

492 Golf Course Circle

7 bedrooms

7 baths

16 guests

Featured Property Arrow at Winter Park Unit 274

Arrow at Winter Park Unit 274

3 bedrooms

3 baths

10 guests

Featured Property Crestview Place Unit 607

Crestview Place Unit 607

3 bedrooms

3 baths

8 guests

Featured Property Bear Crossing 845

Bear Crossing 845

3 bedrooms

3 baths

8 guests

Featured Property 383 County Road 508

383 County Road 508

3 bedrooms

1 baths

8 guests

Featured Property 133 Eisenhower

133 Eisenhower

5 bedrooms

4 baths

10 guests

Featured Property Townhome on Vasquez Creek #5

Townhome on Vasquez Creek #5

3 bedrooms

4 baths

11 guests

Featured Property Twin Rivers Vasquez 3

Twin Rivers Vasquez 3

3 bedrooms

2 baths

9 guests

Featured Property 67 Fireweed 27A

67 Fireweed 27A

4 bedrooms

3 baths

10 guests

Featured Property Ten Mile G-201

Ten Mile G-201

2 bedrooms

2 baths

6 guests

Featured Property 2665 Golden Edge Drive

2665 Golden Edge Drive

4 bedrooms

3 baths

14 guests

Featured Property 701B Quail

701B Quail

3 bedrooms

2 baths

8 guests

Featured Property Snowblaze Condos Building B unit 34

Snowblaze Condos Building B unit 34

3 bedrooms

3 baths

6 guests

Featured Property Silverado I Building B Unit 101

Silverado I Building B Unit 101

3 bedrooms

3 baths

6 guests

Featured Property Townhome on Vasquez Creek #8

Townhome on Vasquez Creek #8

3 bedrooms

4 baths

13 guests

Featured Property 1585 Moose Run

1585 Moose Run

2 bedrooms

1 baths

5 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