Stays for 8+ guests in Winter Park, CO
Stays for 8+ guests in Winter Park, CO, from $175 a night. Book direct on each manager's site, no OTA fee.
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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
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
Zephyr Mountain Lodge # 1706
Lodge · 4 bed · sleeps 12
Winter Park, CO
From $175 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
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
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.
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
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
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 2026-10-30 08:06 UTC. Prices and facts are whatever the manager published on their own site.