Winter Park, Colorado

Vacation Rentals in Winter Park, Colorado

Discover 329 vacation rental properties in Winter Park. From 1 to 9 bedrooms. Average $207/night. 100% have pools.

329 verified listings Book securely on VRBO Prices updated March 2026

329 properties available

Zephyr Mountain Lodge/Slope Side Bldg True Ski/Bike in/ out with patio walk out

Zephyr Mountain Lodge/Slope Side Bldg True Ski/Bike in/ out with patio walk out

1 bed 1 bath
PoolA/CWiFiBalcony
$100/night
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Zephyr Mountain Lodge - Beautifully Renovated

Zephyr Mountain Lodge - Beautifully Renovated

1 bed 1 bath
PoolA/CWiFiBalcony
$144/night
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Newly renovated Winter Park condo on the Fraser River

Newly renovated Winter Park condo on the Fraser River

2 beds 1 bath
PoolA/CWiFiBalcony
$112/night
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Cozy 1-bed, 1-bath condo on the Fraser river in downtown Winter Park, Colorado

Cozy 1-bed, 1-bath condo on the Fraser river in downtown Winter Park, Colorado

1 bed 1 bath
PoolA/CWiFiBalcony
$113/night
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Ski-In, Ski-Out Luxury, Corner Unit. Sleeps 4. Hot Tubs, Pool, 55" TV. Near Base

Ski-In, Ski-Out Luxury, Corner Unit. Sleeps 4. Hot Tubs, Pool, 55" TV. Near Base

1 bed 1 bath
PoolA/CWiFiBalcony
$112/night
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RiverViews TopFlr Private HideawayPark Cozy InTown

RiverViews TopFlr Private HideawayPark Cozy InTown

2 beds 2 baths
PoolA/CWiFiBalcony
$225/night
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Cozy, Clean, DIRECT Ski-in Ski-Out Top-Floor Studio at Iron Horse

Cozy, Clean, DIRECT Ski-in Ski-Out Top-Floor Studio at Iron Horse

1 bath
PoolA/CWiFiBalcony
$145/night
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Cozy Condo- Walk to WP Resort!

Cozy Condo- Walk to WP Resort!

1 bed 1 bath
PoolA/CWiFiBalcony
$127/night
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Dog-friendly condo near the slopes with W/D - pool, hot tub & volleyball

Dog-friendly condo near the slopes with W/D - pool, hot tub & volleyball

2 beds 1 bath
PoolA/CWiFiBalcony
$116/night
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Retro 70s Condo in Winter Park in Colorado's Rocky Mountains!

Retro 70s Condo in Winter Park in Colorado's Rocky Mountains!

1 bed 1 bath
PoolA/CWiFiBalcony
$151/night
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Resort Bliss with Bike Park Access

Resort Bliss with Bike Park Access

1 bath
PoolA/CWiFiBalcony
$171/night
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Ski in/out,2/2,hot tub,K & T/Q/T Bunk,memory foam Q couch/xbox/deck grill/sleep8

Ski in/out,2/2,hot tub,K & T/Q/T Bunk,memory foam Q couch/xbox/deck grill/sleep8

2 beds 2 baths
PoolA/CWiFiBalcony
$165/night
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Walkable, well-appointed riverside condo with pool, & hot tubs

Walkable, well-appointed riverside condo with pool, & hot tubs

1 bed 1 bath
PoolA/CWiFiBalcony
$88/night
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**Downtown** Private Hot Tub, Garage, Fireplace & Washer/Dryer

**Downtown** Private Hot Tub, Garage, Fireplace & Washer/Dryer

1 bed 1 bath
PoolA/CWiFiBalcony
$124/night
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Cozy large studio condo.

Cozy large studio condo.

1 bed 1 bath
PoolA/CWiFiBalcony
$99/night
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Ground-floor studio with mountain views, grill, pool, hot tub, & fireplace

Ground-floor studio with mountain views, grill, pool, hot tub, & fireplace

1 bath
PoolA/CWiFiBalcony
$80/night
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Fully Remodeled, Two Bed, Two Bath, Best Views, Steps from Town

Fully Remodeled, Two Bed, Two Bath, Best Views, Steps from Town

2 beds 2 baths
PoolA/CWiFiBalcony
$215/night
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Winter Park Founders Pointe Slope Side Studio Steps To Base Area

Winter Park Founders Pointe Slope Side Studio Steps To Base Area

1 bath
PoolA/CWiFiBalcony
$110/night
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✔ Check! PET-FRIENDLY | Walk To Downtown | Close To Skiing | Trailhead Lodges 811

✔ Check! PET-FRIENDLY | Walk To Downtown | Close To Skiing | Trailhead Lodges 811

1 bed 1 bath
PoolA/CWiFiBalcony
$130/night
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Walk to Slopes! Newer Condo! Sleeps 4!

Walk to Slopes! Newer Condo! Sleeps 4!

1 bed 1 bath
PoolA/CWiFiBalcony
$97/night
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Beautiful Cozy Studio at the Base With Heated Parking

Beautiful Cozy Studio at the Base With Heated Parking

1 bath
PoolA/CWiFiBalcony
$86/night
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Wild West Hi-Country Condo

Wild West Hi-Country Condo

2 beds 2 baths
PoolA/CWiFiBalcony
$127/night
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Ski-in Ski-out studio

Ski-in Ski-out studio

1 bath
PoolA/CWiFiBalcony
$77/night
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Ski-In/Ski-Out Winter Park Condo w/ Hot Tub Access

Ski-In/Ski-Out Winter Park Condo w/ Hot Tub Access

1 bed 1 bath
PoolA/CWiFiBalcony
$85/night
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Large Glass Front with Beautiful Mountain Views

Large Glass Front with Beautiful Mountain Views

2 beds 2 baths
PoolA/CWiFiBalcony
$149/night
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Renovated water-view retreat with hot tub & heated pool

Renovated water-view retreat with hot tub & heated pool

1 bed 1 bath
PoolA/CWiFiBalcony
$99/night
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Luxury condo in the heart of Town of WP. Access to pool, hot tub & pool table

Luxury condo in the heart of Town of WP. Access to pool, hot tub & pool table

2 beds 1 bath
PoolA/CWiFiBalcony
$159/night
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Zephyr Mountain Lodge 2419 | Extra Large Base Area Condo | Hip & Cool Decor | Foosball Table

Zephyr Mountain Lodge 2419 | Extra Large Base Area Condo | Hip & Cool Decor | Foosball Table

1 bed 1 bath
PoolA/CWiFiBalcony
$117/night
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Ski-in/ski-out studio condo with gas fireplace, pool, hot tub, & mountain view

Ski-in/ski-out studio condo with gas fireplace, pool, hot tub, & mountain view

1 bath
PoolA/CWiFiBalcony
$100/night
View Details → Book on VRBO
Great Condo-Hot tub-Pool-Walk to Rendezvous and Restaurants

Great Condo-Hot tub-Pool-Walk to Rendezvous and Restaurants

1 bath
PoolA/CWiFiBalcony
$97/night
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TRAILHEAD LODGES 223: Book for ski season 2025! Ask about March 7day discounts.

TRAILHEAD LODGES 223: Book for ski season 2025! Ask about March 7day discounts.

3 beds 2 baths
PoolA/CWiFiBalcony
$150/night
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Condo w/ View - 1 Block to Main St - 4 Mi to Ski!

Condo w/ View - 1 Block to Main St - 4 Mi to Ski!

2 beds 2 baths
PoolA/CWiFiBalcony
$168/night
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Walking Distance to Downtown, River and Beautiful Trails - Clean and Cozy!

Walking Distance to Downtown, River and Beautiful Trails - Clean and Cozy!

2 beds 2 baths
PoolA/CWiFiBalcony
$174/night
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Pet Friendly condo located downtown | walk to summer concerts | shared pool/hot tub clubhouse 721

Pet Friendly condo located downtown | walk to summer concerts | shared pool/hot tub clubhouse 721

1 bed 1 bath
PoolA/CWiFiBalcony
$118/night
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Modern Winter Park Condo w/ Community Hot Tub!

Modern Winter Park Condo w/ Community Hot Tub!

2 beds 2 baths
PoolA/CWiFiBalcony
$140/night
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The Trailhead | Beautifully Furnished Modern Condo In Downtown Winter Park

The Trailhead | Beautifully Furnished Modern Condo In Downtown Winter Park

2 beds 2 baths
PoolA/CWiFiBalcony
$171/night
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Resort Bliss with Bike Park Access

Resort Bliss with Bike Park Access

1 bed 1 bath
PoolA/CWiFiBalcony
$126/night
View Details → Book on VRBO
Second-floor condo with fireplace, hot tub & indoor pool - dog-friendly

Second-floor condo with fireplace, hot tub & indoor pool - dog-friendly

1 bed 1 bath
PoolA/CWiFiBalcony
$80/night
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❈ Base Area Condo | Zephyr Mountain Lodge 1218 | Modern Decor | SKI IN SKI OUT | A+ Amenities!

❈ Base Area Condo | Zephyr Mountain Lodge 1218 | Modern Decor | SKI IN SKI OUT | A+ Amenities!

1 bed 1 bath
PoolA/CWiFiBalcony
$118/night
View Details → Book on VRBO
Completely Updated Condo in Great Location only steps to the Gondola

Completely Updated Condo in Great Location only steps to the Gondola

1 bed 1 bath
PoolA/CWiFiBalcony
$119/night
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Pool, Hot Tub, Ski In Ski Out, Bike Storage for Summer Guests

Pool, Hot Tub, Ski In Ski Out, Bike Storage for Summer Guests

1 bed 1 bath
PoolA/CWiFiBalcony
$107/night
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Modern Ski-in/Ski-out Studio with Convenient Access to Communal Hot Tub

Modern Ski-in/Ski-out Studio with Convenient Access to Communal Hot Tub

1 bath
PoolA/CWiFiBalcony
$112/night
View Details → Book on VRBO
Penthouse Studio - Ski In-Out, Iron Horse - Easy Access to Winter Park Base

Penthouse Studio - Ski In-Out, Iron Horse - Easy Access to Winter Park Base

1 bath
PoolA/CWiFiBalcony
$119/night
View Details → Book on VRBO
Two-story ski condo downtown - fireplace, washer/dryer & garage

Two-story ski condo downtown - fireplace, washer/dryer & garage

2 beds 3 baths
PoolA/CWiFiBalcony
$98/night
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Inviting ski-in/ski-out condo with pool, hot tub, gas fireplace, and firepit

Inviting ski-in/ski-out condo with pool, hot tub, gas fireplace, and firepit

1 bath
PoolA/CWiFiBalcony
$90/night
View Details → Book on VRBO
Cozy Condo on Vasquez Creek w/ Free Shuttle Access

Cozy Condo on Vasquez Creek w/ Free Shuttle Access

2 beds 2 baths
PoolA/CWiFiBalcony
$118/night
View Details → Book on VRBO
Ski-In/Ski-Out Studio with Gas Fireplace & Shared Pool, Hot Tub, Gym, Game Room

Ski-In/Ski-Out Studio with Gas Fireplace & Shared Pool, Hot Tub, Gym, Game Room

1 bed 1 bath
PoolA/CWiFiBalcony
$102/night
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Downtown walk to bars, restaurants Trailhead 212

Downtown walk to bars, restaurants Trailhead 212

1 bed 1 bath
PoolA/CWiFiBalcony
$133/night
View Details → Book on VRBO

Showing 48 of 329 properties

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