Stays for 10+ guests in Winter Park, CO
Stays for 10+ guests in Winter Park, CO, from $123 a night. Book direct on each manager's site, no OTA fee.
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Stays, best documented first
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
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
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
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.
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
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 07:56 UTC. Prices and facts are whatever the manager published on their own site.