Stays for 6+ guests in Winter Park, CO

Stays for 6+ guests in Winter Park, CO, from $84 a night. Book direct on each manager's site, no OTA fee.

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Private Sauna, Covered Parking, Hot Tub, Pool!
House · 2 bed · 2 bath · sleeps 6
Winter Park, CO
From $84 a night
- mountain view
- kitchen
- wifi
- free carport on premises – 2 spaces
Exact location
Book direct on HostWise Stays
Mountain Ridge Suite
Condo · 2 bed · 2 bath · sleeps 6
Winter Park, CO
From $649 a night
- ski-in/ski-out
- wifi
- hot tub
- fireplace
Exact location
Book direct on Slopeside Condo Rentals at Winter Park Ski Resort
Alpine Vista Condo
Condo · 3 bed · 2 bath · sleeps 8
Winter Park, CO
From $749 a night
- ski-in/ski-out
- wifi
- hot tub
- fireplace
Exact location
Book direct on Slopeside Condo Rentals at Winter Park Ski Resort
Stunning BRAND NEW Luxury condo in heart of downtown WP on the top floor
Condo · 2 bed · 2 bath · sleeps 10
Winter Park, CO
From $338 a night
- balcony
- barbecue grill
- blender
- coffee/tea maker
City-level location
Book direct on Book Vacation Rentals, Holiday Rental Homes Directly From Owners
NEW Ski In/Out Condo with Hot Tub & Balcony
House · 2 bed · 1 bath · sleeps 6
Winter Park, CO
From $269 a night
Exact location
Book direct on House Swap for Airbnb Hosts, No Nightly Rates
Four-story townhome with private hot tub, roof deck & big mountain views
Townhome · 3 bed · 3 bath · sleeps 6
Winter Park, CO
From $298 a night
- available in the house: internet access
- balcony
- barbecue grill
- dryer
City-level location
Book direct on Book Vacation Rentals, Holiday Rental Homes Directly From Owners
Best Views In WinterPark | FamilyFriendly | Garage
House · 3 bed · 3 bath · sleeps 6
Winter Park, CO
From $327 a night
Exact location
Book direct on House Swap for Airbnb Hosts, No Nightly Rates
New creek side chateau guest suite! Booking for summer NOW! With hot tub!
House · 2 bed · 2 bath · sleeps 6
Winter Park, CO
From $342 a night
- at least 80% lighting from leds
- balcony
- barbecue grill
- birdwatching
City-level location
Book direct on Book Vacation Rentals, Holiday Rental Homes Directly From Owners
Luxurious Townhome With 3 En-suites, Gorgeous Views and Private Hot Tub!
Townhome · 3 bed · 4 bath · sleeps 10
Winter Park, CO
From $358 a night
- balcony
- barbecue grill
- deck or patio
- dining area
City-level location
Book direct on Book Vacation Rentals, Holiday Rental Homes Directly From Owners
Experience Luxury And Adventure At 143 Dreamcatcher, A Spacious 5-bedroom Home In Winter Park, Co
House · sleeps 11
Winter Park, CO
From $811 a night
- concierge
- dryer
- fire extinguisher
- fireplace
Exact location
Book direct on Niranar
2 Mi to Winter Park Resort: Condo w/ Pool Access!
Condo · 4 bed · sleeps 12
Winter Park, CO
From $123 a night
City-level location
Book direct on Savvy
Close to slopes-Walk to Downtown Winter Park!
House · 2 bed · 2 bath · sleeps 8
Winter Park, CO
No nightly rate published
- kitchen
- wifi
- dedicated workspace
- free parking garage on premises
Exact location
Book direct on AirINN
New Condo Downtown Winter Park-Close to the Slopes
House · 2 bed · 2 bath · sleeps 6
Winter Park, CO
No nightly rate published
- kitchen
- wifi
- dedicated workspace
- free parking garage on premises
Exact location
Book direct on AirINN
Tipsy Fox @ Downtown Winter Park Near the Slopes!
House · 1 bed · 1 bath · sleeps 6
Winter Park, CO
No nightly rate published
- kitchen
- wifi
- dedicated workspace
- free parking garage on premises
Exact location
Book direct on AirINN
262 Star Ridge West
Townhome · 4 bed · sleeps 10
Winter Park, CO
No nightly rate published
- bbq area
- bed linens
- car necessary - no public transportation
- carbon monoxide detector
Exact location
Book direct on Colorado Vacation Homes, Rentals & Condos
308 Valley Ranch Lodge
Lodge · 4 bed · sleeps 10
Winter Park, CO
No nightly rate published
- bbq area
- bed linens
- car necessary - no public transportation
- carbon monoxide detector
Exact location
Book direct on Colorado Vacation Homes, Rentals & Condos
665 Edgerun Haus
Townhome · 4 bed · sleeps 12
Winter Park, CO
No nightly rate published
- bbq area
- bed linens
- car necessary - no public transportation
- carbon monoxide detector
Exact location
Book direct on Colorado Vacation Homes, Rentals & Condos
Little Red Ski Haus, 2min walk to Winter Park lift
House · 3 bed · 2 bath · sleeps 7
Winter Park, CO
No nightly rate published
- high chair
- room darkening shades
- wine glasses
- outdoor dining area
Exact location
Book direct on Manage your vacation home with Fairly.
Ramble On House
House · 4 bed · 3.5 bath · sleeps 10
Winter Park, CO
No nightly rate published
- rooftop hot tub and fire pit
- cedar barrel sauna and cold plunge
- red light therapy
- 100-inch private theater
Exact location
Book direct on Gather Destinations
Silverado II Rentals By StayWinterPark
Condo · 4 bed · 4 bath · sleeps 8
Winter Park, CO
No nightly rate published
Exact location
Book direct on Colorado Vacation Homes, Rentals & Condos
"Sweeping Mountain, Pond views: 88 Steps to Trail"
Condo · 3 bed · sleeps 8
Winter Park, CO
No nightly rate published
- air conditioning
- cleaning products
- dishes and silverware
- dryer
Exact location
Book direct on Beachfront Bliss and Scenic Mountain Retreats
3BR Cozy Townhome | Walk to Town | Skiing Close By
Townhome · 3 bed · sleeps 9
Winter Park, CO
No nightly rate published
- dedicated workspace
- office
- desk
- baking sheet
Exact location
Book direct on Manage your vacation home with Fairly.
Alpine Retreat Near Winter Park Resort
House · 4 bed · sleeps 10
Winter Park, CO
No nightly rate published
- free parking
- dryer
- washing machine
- dishwasher
Exact location
Book direct on Manage your vacation home with Fairly.
Hi Country Haus 3 bedroom Riverfront Condo
Condo · 3 bed · sleeps 7
Winter Park, CO
No nightly rate published
- bathtub
- shower
- hair dryer
- tv
Exact location
Book direct on Manage your vacation home with Fairly.
Ski Retreat Condo w/ Pool, Hot Tub & Balconies
Condo · 2 bed · sleeps 7
Winter Park, CO
No nightly rate published
- hot tub
- pool
- carbon monoxide alarm
- smoke alarm
Exact location
Book direct on Manage your vacation home with Fairly.
Winter Park Escape -Luxury, Hot Tub, Pet Friendly
Townhome · 3 bed · sleeps 9
Winter Park, CO
No nightly rate published
- dedicated workspace
- dryer
- ev charger
- heating
Exact location
Book direct on Manage your vacation home with Fairly.
Après Above It All, Rooftop Hot Tub I Walkable
House · 4 bed · 3 bath · sleeps 8
Winter Park, CO
No nightly rate published
Exact location
Book direct on Luxury Vacation Rentals and Vacation Homes by Wander
Brand New I Downtown Winter Park w/Hot Tub
House · 4 bed · 3 bath · sleeps 8
Winter Park, CO
No nightly rate published
Exact location
Book direct on Luxury Vacation Rentals and Vacation Homes by Wander
Cozy Mountain Getaway Next to Chairlift I Winter Park
Condo · 2 bed · 3 bath · sleeps 6
Winter Park, CO
No nightly rate published
Exact location
Book direct on Epic Property Management
Founders Pointe Ski In/Out Condo 4549
House · 2 bed · 2 bath · sleeps 6
Winter Park, CO
No nightly rate published
Exact location
Book direct on Luxury Vacation Rentals and Vacation Homes by Wander
Lakota Dreamcatcher Villa 160
House · 5 bed · 4.5 bath · sleeps 13
Winter Park, CO
No nightly rate published
Exact location
Book direct on Luxury Vacation Rentals and Vacation Homes by Wander
Landing Creekside Villa 15
House · 4 bed · 3 bath · sleeps 12
Winter Park, CO
No nightly rate published
Exact location
Book direct on Luxury Vacation Rentals and Vacation Homes by Wander
Ramble Retreat I Downtown Winter Park w/Hot Tub
House · 4 bed · 4 bath · sleeps 10
Winter Park, CO
No nightly rate published
Exact location
Book direct on Luxury Vacation Rentals and Vacation Homes by Wander
Row Roof Top Penthouse 141
House · 4 bed · 4 bath · sleeps 12
Winter Park, CO
No nightly rate published
Exact location
Book direct on Luxury Vacation Rentals and Vacation Homes by Wander
Sojourn Luxury Villa 115
House · 3 bed · 3.5 bath · sleeps 8
Winter Park, CO
No nightly rate published
Exact location
Book direct on Luxury Vacation Rentals and Vacation Homes by Wander
Telemark River Front Villa 522
House · 3 bed · 2 bath · sleeps 8
Winter Park, CO
No nightly rate published
Exact location
Book direct on Luxury Vacation Rentals and Vacation Homes by Wander
Newly Renovated Winter Park Townhouse
Townhome · 3 bed · sleeps 9
Winter Park, CO
No nightly rate published
Exact location
Book direct on Sawmill Haus
Northstar at Après Winter Park
Apartment · sleeps 6
Winter Park, CO
No nightly rate published
- children welcome
- infants welcome
- smoking not allowed
- wheelchair inaccessible
Exact location
Book direct on Northstar Properties

How prices are computed

Lowest rate the manager has published. Your dates may cost more; the real price is on their site. The "from" figure is the lowest nightly rate the manager published on that listing page when we last fetched it. It excludes taxes, cleaning and other fees, it is not a quote, and it is not live availability.

Updated 2026-10-31 08:42 UTC. Prices and facts are whatever the manager published on their own site.