Winter Park Vacation Rentals


Winter Park Lodging Accommodations 

Experience all that Winter Park has to offer by booking your stay today! At StayWinterPark, we have a wide selection of vacation rentals suitable for groups of any size.  Whether you're traveling with a small group or a large one, we have the perfect accommodation for you.  No matter the time of year, we can assist you in finding the ideal place to stay during your Colorado vacation.

Popular Searches: Private Homes, Colorado Cabins,  Luxury Vacation Rentals, Pet Friendly Rentals, Downtown Winter Park, Condo Complexes, Townhome rentals, Winter Park Base Village and Ski In Ski Out

Other popular options include Fraser, Tabernash, Granby  and Grand Lake.

Properties Available 16 properties available
Why You’ll Love this Colorado Escape•5. 6 miles to Winter Park Resort and 30 yards to the free town shuttle• Access to Club Meadow Ridge with heated pool and hot tubs just 0.2 mile away• Wood burning fireplace and private deck with stunning mountain views• Sleeps up to 4 across two bedrooms• Fast Wi-Fi and designated workstation• Professionally Ma
Hot HOT 15
Meadow Ridge Court 22 Unit 15
Condo
Bedrooms 2 bedrooms
Bathrooms 1 baths
Guests 4 guests
Welcome to our condo at Meadow Ridge Court 28 Unit #6! Check out this spacious 3-bedroom vacation rental in Fraser! It comes with access to a pool, hot tubs, tennis courts, and workout facilities, all within a generous 1,101 square feet of living space spread across a tri-level floor plan. Plus, you'll love the private deck right off the main livin
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 28 Unit 6
Condo -
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 4.9 32
Welcome to our condo at Meadow Ridge Court 18 Unit #4! Just recently updated, this cozy ground floor one-bedroom apartment is the ideal spot to relax and recharge. Step out onto the private patio right from the main living room, where you can soak in views of the Winter Park Resort, all just a quick stroll from the main clubhouse. Inside, the livin
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 18 Unit 4
Condo -
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 4.8 27
Welcome to our condo at Meadow Ridge Court 8 Unit #6! Check out this beautifully decorated 2-bedroom Fraser vacation rental! It features 3 comfy queen beds, a newly remodeled kitchen, and a private patio where you can soak in stunning mountain views. Plus, it's just a stone's throw away from the main clubhouse! Step into this delightful, newly reno
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 4.7 28
Why You’ll Love this Colorado Escape• 5.9 miles to Winter Park Ski Resort and 25 yards to the free town shuttle• Access to the Club Meadow Ridge heated pool and hot tubs • Private deck with stunning mountain views and an indoor electric fireplace• Complimentary Wi-Fi and remote work station• Professionally Managed by Stay Winter ParkThe CondoThis
Hot HOT 10
Meadow Ridge Court 20 Unit 14
Condo -
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 6 guests
Rating 5 1
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 and provide
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 131
Condo - Pet Friendly
Bedrooms 3 bedrooms
Bathrooms 2 baths
Guests 9 guests
Rating 5 256
Welcome to our condo at Meadow Ridge Court 29 Unit #8! Check out this stunning townhome-style condo! It features 3 spacious bedrooms, a private deck that boasts breathtaking mountain views, and an inviting open floor plan. With a generous layout spread over 3 levels, this recently renovated gem is perfect for families looking to rent in Fraser. Plu
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 29 unit 8
Townhome -
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 4.8 19
Situated within the Trailhead Lodges complex and conveniently positioned along the shuttle route, this property serves as the ideal ski getaway for couples, small families or two individuals in search of cozy accommodations. This delightful one bedroom unit is also in close proximity to the Rendezvous Event Center, which features a sledding hill s
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 731
Condo -
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 4.9 141
Welcome to our condo at Meadow Ridge Pines B-7 Court 42! Plan your next ski or summer escape at our family-friendly 3-bedroom condo, complete with fantastic clubhouse amenities. Our spacious and beautifully renovated split-level condo features a private deck where you can soak in the serene forest views. Step into the heart of this condominium, whe
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 Pines B-7 Court 42
Condo -
Bedrooms 3 bedrooms
Bathrooms 3 baths
Guests 8 guests
Rating 5 26
Trailhead 821 is an excellent destination for families and is pet friendly, offering a sledding hill suitable for all ages, as well as fire pits for warming up at the Rendezvous Event Center. In the summer, visitors can enjoy the skate park and outdoor gymnasium. The property is conveniently accessible via the free town shuttle, making it an idea
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 821
Condo - Pet Friendly
Bedrooms 1 bedrooms
Bathrooms 1 baths
Guests 4 guests
Rating 4.9 134
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 4.9 101
Welcome to our condo at Meadow Ridge Court 20 Unit #13! Escape to this stunningly remodeled 2nd-floor condo in Fraser, Colorado. This charming 2-bedroom retreat boasts a sleek Ikea kitchen, a cozy wood-burning fireplace, and can comfortably accommodate up to 5 guests. You'll love the easy access to the clubhouse and lift stops, along with handy ame
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 20 Unit 13
Condo -
Bedrooms 2 bedrooms
Bathrooms 2 baths
Guests 5 guests
Rating 4.9 32

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