Stay Winter Park

What Stay Winter Park does

Stay Winter Park is a privately held, locally owned vacation rental and property management company headquartered at 50 Village Drive, Winter Park, Colorado. Founded in 1972, it manages a portfolio of 200+ short-term rental properties - including cabins, condos, townhomes, ski-in/ski-out units, luxury homes, and pet-friendly properties - across five Colorado mountain communities: Winter Park, Fraser, Tabernash, Granby, and Grand Lake. The company serves individual leisure travelers, families, ski groups, wedding and corporate groups, and the homeowners who supply its inventory.

The technology backbone is the third-party TrackHS property management system, which powers the direct-booking website (staywinterpark.com), availability calendars, pricing, and a guest portal that delivers contactless check-in with electronic door codes after final payment. A TrackHS owner portal provides homeowners with reservation calendars and financial reporting. Distribution is multi-channel: direct website and 1-800 phone reservations are supplemented by listings on Airbnb, VRBO, Expedia, Booking.com, and Winter Park Resort, with Stripe handling payment processing. The company also curates ancillary partnerships (ski rental delivery, equipment shops, local transportation, travel insurance) to round out the guest experience.

The business operates two revenue streams. The first is a transaction-fee model on bookings: guests pay nightly rates and Stay Winter Park collects booking fees and/or a share of rental revenue. The second is a recurring property management services arm (hosted on dedicated Winter Park, Granby, and Grand Lake microsites) where the company charges homeowners for listing management, guest services, maintenance coordination, and rental income management. Promotional levers - 20% off for 7-21 night stays (LTR26 code) and a new property 15% off code - suggest off-peak and supply-acquisition strategies. The company remains privately held with no disclosed institutional ownership or funding.

Name

Stay Winter Park

Legal name

Stay Winter Park

Website

https://staywinterpark.com

Company type

Private

Founded year

1972

Operating status

Operating

Headcount range

11–50 employees

Short description

Stay Winter Park is a locally owned Winter Park, Colorado vacation rental and property management firm, founded in 1972, managing 200+ cabins, condos, and luxury homes across five mountain communities for leisure travelers, ski groups, and event clients.

Ownership category

akta.pro rank

Product category

Vacation Rental Services

SIC

Hotels, Rooming Houses, Camps & Other Lodging Places (7000), Real Estate Agents & Managers (For Others) (6531)

akta.pro primary industry

Mountain & Ski Homes (THAMAAAG)

akta.pro secondary industries

Snow & Mountain Unique Stays (Chalets, Ski Cabins) (THAMADAL), Luxury Chalets & Ski-In/Ski-Out Homes (THAMAEAD)

Keywords

• Vacation rental management
• Mountain lodging services
• Ski resort rentals
• Cabin rentals
• Vacation property management

Headquarters

HQ city

Winter Park

HQ country

United States

HQ region

North America

Offices1 record

Markets served

GTM type

B2C

Offering type

Services

Cost components

Personnel, Operations, Marketing or Sales, Technology or R&D, Infrastructure

Revenue model

1. Vacation Rental Bookings: Revenue generated from booking vacation rental properties including cabins, condos, townhomes, and luxury homes. Hosts pay a fee for property management services while guests pay for nightly accommodations.
2. Property Management Services: Services for property owners including rental management, maintenance coordination, and guest services for homeowners in Winter Park, Granby, and Grand Lake areas.

Pricing tiers

Go-to-market motion1 record

Distribution channels6 records

Marketing channels9 records

Core offering

Stay Winter Park rents and manages 200+ short-term vacation rental properties (cabins, condos, townhomes, luxury homes, and ski-in/ski-out units) across Winter Park, Fraser, Tabernash, Granby, and Grand Lake in Colorado. The company also provides property management services to homeowners in Winter Park, Granby, and Grand Lake, handling listings, guest services, maintenance, and rental income management. All bookings are powered by a TrackHS platform with contactless check-in and a guest portal.

Product overview

Stay Winter Park operates as a locally owned vacation rental management company (in business since 1972) offering a portfolio of 200+ short-term rental properties across five Colorado mountain communities: Winter Park, Fraser, Tabernash, Granby, and Grand Lake. The core product is the Vacation Rentals platform, which encompasses diverse property types including cabins, condos, townhomes, private homes, luxury properties, and ski-in/ski-out rentals. Supporting products include pet-friendly rentals, long-term/flexible stays, and holiday getaway packages. A complementary property management service arm provides homeowners in Winter Park, Granby, and Grand Lake with listing, guest services, and rental income management. The guest experience is powered by a TrackHS-based guest portal delivering contactless check-in, electronic door codes, and property maps, while owners use a corresponding TrackHS owner portal for financial and reservation management. A group bookings service handles ski groups, weddings, reunions, and corporate retreats. The company also integrates third-party partners for ski rentals, equipment delivery, and local transportation to round out the guest experience.

Differentiator

Problem solved

Functional benefit

Products and services

• Winter Park Vacation Rentals Short-term vacation rental properties including cabins, condos, townhomes, private homes, and luxury retreats across Winter Park, Fraser, Tabernash, Granby, and Grand Lake, Colorado. The primary offering managed by Stay Winter Park for guest bookings.
• Ski In/Ski Out Rentals Specialized vacation rentals positioned for direct access to ski slopes, including properties in the Resort Base Village near Mary Jane's legendary mogul runs.
• Luxury Properties Premium vacation rental homes and cabins featuring high-end furnishings, private hot tubs, and enhanced amenities targeting affluent travelers.
• Pet Friendly Rentals Vacation rental properties that accommodate pets, allowing guests to travel with their dogs or other animals.
• Long Term Rentals Extended-stay vacation rental options for guests seeking multi-week or monthly accommodations in the Winter Park area, with a 20% discount for 7-21 night stays available under promo code LTR26.
• Flexible Stays Flexible short-term rental options with adaptable booking terms, including special promotional rates for 7-21 night stays under promo code LTR26.
• Holiday Getaways Specialized vacation rental packages and property selections for holiday travel periods including Labor Day, Thanksgiving, and Christmas.
• Group Bookings & Corporate Retreats Specialized booking services for ski groups, weddings, reunions, and corporate/executive retreats, including dedicated group inquiry and coordination support.
• Winter Park Property Management Property management services for homeowners in the Winter Park area, including property listing, guest services, maintenance, and rental income management.
• Granby Property Management Property management services for homeowners in the Granby area, covering property listing, guest services, and rental management.
• Grand Lake Property Management Property management services for homeowners in the Grand Lake area.
• Guest Portal Online guest portal (powered by TrackHS) providing check-in information including maps to vacation rentals, electronic door codes, and Wi-Fi details sent to guests after final payment is processed.

Quantifiable outcome

• No additional booking fees when booking direct
• +1 more outcomes

Named customers4 records

Segments5 records

Ideal customer profiles3 records

Technology focussed No

API detail

Has API

No

API docs

API detail

Core technology

AI maturity

App detail

Integration10 records

Feature3 records

Partnerships

Five partnerships are on record, tiered minor and core.

• Red Sky Travel InsuranceminorGTM or Marketing PartnerRed Sky Travel Insurance is partnered with Stay Winter Park to offer travel insurance products to guests, including Trip Preserver coverage for trip cancellation protection. Company strongly recommends guests purchase travel insurance.
• Black Tie Ski Rental DeliveryminorChannel Partner/ Reseller/ DistributorPartner provides ski rental delivery services to vacation rental properties, offering guests convenient equipment rental without leaving the property.
• Beavers Sport ShopminorChannel Partner/ Reseller/ DistributorLocal ski and snowboard rental shop providing equipment rental services for guests visiting Winter Park.
• Home James TransportationminorGTM or Marketing PartnerTransportation service partner providing shuttle/transportation options for guests, referenced in the Explore section of the website.
• TrackHScoreTechnology or IntegrationProperty management software platform used for booking engine, guest portals, and property management operations. Powers the online booking system and guest communication tools.

Scale indicators3 records

Recent moves6 records

Expansion highlights5 records

Direct peers

• Vacasa: Vacasa is the largest professional vacation rental management company in North America, offering full-service property management and direct booking across 30,000+ homes in U.S. ski and beach destinations. It directly competes with Stay Winter Park for both homeowner supply and guest demand in Colorado mountain markets.
• SkyRun Vacation Rentals: SkyRun is a vacation rental management company with a strong presence in Colorado mountain destinations including Steamboat Springs, Breckenridge, and Winter Park. It uses a hybrid franchise/local-operator model that directly mirrors Stay Winter Park's locally owned, professionally managed approach.
• Evolve Vacation Rental: Evolve is a national vacation rental manager with a lighter-touch, fee-based model serving 80,000+ properties across U.S. destinations, including Colorado ski towns. It targets the same homeowner supply and traveler segments as Stay Winter Park, with a heavier emphasis on tech-enabled distribution.
• Winter Park Resort Lodging: Winter Park Resort operates its own on-mountain lodging properties and is Stay Winter Park's most direct local competitor for ski-in/ski-out guests during the winter season. It captures captive demand from lift ticket holders that Stay Winter Park must compete for through location and amenity differentiation.
• iTrip Vacations: iTrip is a franchise-based short-term rental management company operating in 90+ U.S. destinations, including several Colorado mountain towns. It competes for the same homeowner supply and guest base as Stay Winter Park, particularly in drive-to ski markets.

Broad incumbents

• VRBO: VRBO (owned by Expedia Group) is a major U.S. vacation rental marketplace that distributes Stay Winter Park inventory to family-oriented travelers. It is a key OTA channel but also a competitor as it bundles property listings with Expedia's broader travel marketplace and Tripadvisor content.
• Airbnb: Airbnb is the dominant global vacation rental marketplace on which Stay Winter Park lists inventory. It is a distribution channel and indirect competitor: Airbnb increasingly promotes its own hosted experiences and flexible search, competing for the same guests while also setting visibility rules for Stay Winter Park's listings.
• Sonder Holdings: Sonder operates a tech-forward portfolio of short-stay apartments and boutique hotels across major cities, with a smaller mountain presence. It represents the broader, professionally managed, brand-driven short-stay category that competes for the same premium leisure guests Stay Winter Park targets.
• Homes & Villas by Marriott Bonvoy: Homes & Villas is Marriott's vacation rental program offering professionally managed whole-home rentals, including in select U.S. mountain destinations. It targets the same luxury and premium leisure traveler that Stay Winter Park's luxury retreat segment addresses, leveraging Marriott's loyalty and brand trust.

Regional players

• Mountainside Resort Properties: Mountainside Resort Properties is a Grand County-area vacation rental and property management company operating around Winter Park and Granby. It is a near-identical local peer competing for the same homeowner supply and guest demand in the same micro-market as Stay Winter Park.

Market position

Strengths5 records

Weaknesses5 records

Competitive moat4 records

Key risks6 records

Key highlights7 records

Customer concentration

• Xx.com/StayWinterPrkCO
• YouTubeyoutube.com/c/VacationsincWinterParkCO
• Facebookfacebook.com/StayWinterPark
• Instagraminstagram.com/staywinterpark
• Pinterestpinterest.com/StayWinterPark
• LinkedInlinkedin.com/company/staywinterpark

Revenue estimate

Valuation estimate

Number of profiles

Funding overview

Funding rounds

Investors

Funding detail is available on the Subscription and Enterprise plan.Contact sales →

M&A

Investments

M&A and investment is available on the Subscription and Enterprise plan.Contact sales →

Frequently asked questions about Stay Winter Park