<PAGE>   1
AS FILED WITH THE SECURITIES AND EXCHANGE COMMISSION ON JULY 1, 1999
                                                      REGISTRATION NO. 33-______
================================================================================
                       SECURITIES AND EXCHANGE COMMISSION
                             WASHINGTON, D.C. 20549

                                    FORM S-8
                             REGISTRATION STATEMENT
                                      UNDER
                           THE SECURITIES ACT OF 1933

                             TRENDWEST RESORTS, INC.
             (EXACT NAME OF REGISTRANT AS SPECIFIED IN ITS CHARTER)

       OREGON                                               93-1004403
       (STATE OR OTHER JURISDICTION                         (I.R.S. EMPLOYER
       OF INCORPORATION OR ORGANIZATION)                    IDENTIFICATION NO.)

       9805 WILLOWS ROAD, REDMOND, WASHINGTON               98052
       --------------------------------------               -------
       (ADDRESS OF PRINCIPAL EXECUTIVE OFFICES)             (ZIP CODE)


               TRENDWEST RESORTS 1999 EMPLOYEE STOCK PURCHASE PLAN
                TRENDWEST RESORTS 1997 EMPLOYEE STOCK OPTION PLAN
                            (FULL TITLE OF THE PLAN)

                                GARY A. FLORENCE
                   VICE PRESIDENT AND CHIEF FINANCIAL OFFICER
                             TRENDWEST RESORTS, INC.
                                9805 WILLOWS ROAD
                            REDMOND, WASHINGTON 98052
                     (NAME AND ADDRESS OF AGENT FOR SERVICE)

                                 (425) 498-2500
          (TELEPHONE NUMBER, INCLUDING AREA CODE, OF AGENT FOR SERVICE)

                         CALCULATION OF REGISTRATION FEE

<TABLE>
<CAPTION>
===================================================================================================
                                          PROPOSED MAXIMUM       PROPOSED
      TITLE OF                             OFFERING PRICE         MAXIMUM           AMOUNT OF
     SECURITIES         AMOUNT TO BE            PER              AGGREGATE         REGISTRATION
  TO BE REGISTERED       REGISTERED            SHARE          OFFERING PRICE (1)     FEE (1)
---------------------------------------------------------------------------------------------------
<S>                     <C>               <C>                 <C>                  <C>
   COMMON STOCK,           SHARES
 WITHOUT PAR VALUE        1,356,451           $21.4375         $ 29,073,832         $8,082.52
===================================================================================================
</TABLE>

(1) THE PROPOSED MAXIMUM OFFERING PRICE PER SHARE AND THE REGISTRATION FEE WERE
CALCULATED IN ACCORDANCE WITH RULE 457(h) UNDER THE ACT BASED ON THE AVERAGE OF
THE HIGH AND LOW PRICES FOR TRENDWEST RESORTS, INC. COMMON STOCK ON JUNE 16,
1999, AS QUOTED BY THE NASDAQ NATIONAL MARKET SYSTEM.


                     EXHIBIT INDEX IS LOCATED ON PAGE II-5.

<PAGE>   2

                                     PART II

                    INFORMATION REQUIRED IN THE REGISTRATION
                                    STATEMENT

ITEM 3.  INCORPORATION OF DOCUMENTS BY REFERENCE.

The following documents filed or to be filed with the Commission by the
registrant are incorporated by reference in this registration statement.

        (a)    The Company's Annual Report on Form 10-K for the fiscal year
               ended December 31, 1998, filed with the Commission pursuant to
               Section 13(a) of the Securities Exchange Act of 1934, as amended
               (the "Exchange Act").

        (b)    All other reports filed pursuant to Section 13(a) or 15(d) of the
               Exchange Act since end of the fiscal year covered by the
               Company's Annual Report on Form 10-K referred to in (a) above.

        (c)    The description of the Company's Common Stock contained in a
               registration statement on Form 8-A filed pursuant to Section 12
               of the Exchange Act (Registration No.000-22979).

        (d)    All documents filed by the Company pursuant to Sections 13(a),
               13(c), 14 or 15(d) of the Exchange Act after the date hereof and
               prior to the filing of a post-effective amendment which indicates
               that all securities offered have been sold or which deregisters
               all securities then remaining unsold shall be deemed to be
               incorporated by reference herein and to be a part hereof from the
               date of filing of such documents.

ITEM 4.  DESCRIPTION OF SECURITIES.

Not Applicable

ITEM 5.  INTERESTS OF NAMED EXPERTS AND COUNSEL.

None

ITEM 6.  INDEMNIFICATION OF DIRECTORS AND OFFICERS.

        The Company's Articles of Incorporation provide that the liability of
the directors of the Company for monetary damages will be eliminated to the
fullest extent permissible under Oregon law. This is intended to eliminate the
personal liability of a director for monetary damages in an action brought by or
in the right of the Company for breach of a director's duties or the Company or
its stockholders except for liability (i) for any breach of the director's duty
of loyalty to the Company or its stockholders, (ii) for acts or omissions not in
good faith or which involve intentional misconduct or knowing violation of law,
(iii) for any unlawful distribution to stockholders, or (iv) for any transaction
from which the director derived an improper personal benefit. This provision
does not limit or eliminate the rights of the Company or any stockholder to seek
non-monetary relief, such as an injunction or rescission, in the event of a
breach of a director's duty of care. This provision also does not affect the
director's responsibilities under any other laws, such as the federal or state
securities or environmental laws.

        The Articles of Incorporation and the Bylaws also provide that the
Company shall indemnify, to the fullest extent permitted under Oregon law, any
person who has been made, or is threatened to be made, a party to an action,
suit or legal proceeding by reason of the fact that the person is or was a
director or officer of the Corporation. The Company intends to enter into
separate indemnification agreements with each of its directors. These agreements
will require the Company to indemnify its directors to the fullest extent
permitted by law, including circumstances in which indemnification would
otherwise be discretionary. Among other things, the agreements require the
Company to indemnify directors against certain liabilities that may arise by
reason of their status or service as a director and to



                                   Page II-1
<PAGE>   3

advance their expenses incurred as a result of any proceeding against them as to
which they could be indemnified. The Company also intends to obtain insurance on
behalf of its executive officers and directors for certain liabilities arising
out of their actions in such capacities. The Company believes that these
contractual arrangements, the provisions in its Articles of Incorporation and
Bylaws and insurance coverage are necessary to attract and retain qualified
persons as directors and officers.

    ITEM 7.  EXEMPTION FROM REGISTRATION CLAIMED.

Not Applicable

ITEM 8.  EXHIBITS.

<TABLE>
<CAPTION>
Exhibit Number      Exhibit
--------------      -------
<S>                 <C>
      4.1           Trendwest Resorts, Inc. 1999 Employee Stock Purchase Plan

      4.2           Trendwest Resorts, Inc. 1997 Employee Stock Option Plan

      5.1           Opinion of Heller Ehrman White & McAuliffe

     23.1           Consent of Heller Ehrman White & McAuliffe (See Exhibit 5.1)

     23.2           Consent of KPMG LLP, Independent Auditors

     24             Power of Attorney (See page II-4 of this Registration
                    Statement)
</TABLE>


ITEM 9.  UNDERTAKINGS.

        (a)    The undersigned registrant hereby undertakes:

               (1) To file, during any period in which offers or sales are being
made, a post-effective amendment to this registration statement:

                      (i) To include any prospectus required by section 10(a)(3)
of the Securities Act of 1933;

                      (ii) To reflect in the prospectus any facts or events
arising after the effective date of the registration statement (or the most
recent post-effective amendment thereof) which, individually or in the
aggregate, represent a fundamental change in the information set forth in the
registration statement;

                      (iii) To include any material information with respect to
the plan of distribution not previously disclosed in the registration statement
or any material change to such information in the registration statement;
Provided, however, that paragraphs (a)(1)(i) and (a)(1)(ii) do not apply if the
registration statement is on Form S-3, Form S-8 or Form F-3, and the information
required to be included in a post-effective amendment by those paragraphs is
contained in periodic reports filed by the registrant pursuant to section 13 or
section 15(d) of the Securities Exchange Act of 1934 that are incorporated by
reference in this registration statement.

               (2) That, for the purpose of determining any liability under the
Securities Act of 1933, each such post-effective amendment shall be deemed to be
a new registration statement relating to the securities offered therein, and the
offering of such securities at that time shall be deemed to be the initial bona
fide offering thereof.

               (3) To remove from registration by means of a post-effective
amendment any of the securities being registered which remain unsold at the
termination of the offering.

        (b) The undersigned registrant hereby undertakes that, for purposes of
determining any liability under the Securities Act of 1933, each filing of the
registrant's annual report pursuant to section 13(a) or section 15(d) of the



                                   Page II-2
<PAGE>   4

Securities Exchange Act of 1934 (and, where applicable, each filing of an
employee benefit plan's annual report pursuant to Section 15(d) of the
Securities Exchange Act of 1934) that is incorporated by reference in the
registration statement shall be deemed to be a new registration statement
relating to the securities offered therein, and the offering of such securities
at that time shall be deemed to be the initial bona fide offering thereof.

        (e) The undersigned registrant hereby undertakes to deliver or cause to
be delivered with the prospectus, to each person to whom the prospectus is sent
or given, the latest annual report to security holders that is incorporated by
reference in the prospectus and furnished pursuant to and meeting the
requirements of Rule 14a-3 or Rule 14c-3 under the Securities Exchange Act of
1934; and, where interim financial information required to be presented by
Article 3 of Regulations S-X is not set forth in the prospectus, to deliver, or
cause to be delivered to each person to whom the prospectus is sent or given,
the latest quarterly report that is specifically incorporated by reference in
the prospectus to provide such interim financial information.

        (h) Insofar as indemnification for liabilities arising under the
Securities Act of 1933 may be permitted to directors, officers and controlling
persons of the registrant pursuant to the foregoing provisions, or otherwise,
the registrant has been advised that in the opinion of the Securities and
Exchange Commission such indemnification is against public policy as expressed
in the Act and is, therefore, unenforceable. In the event that a claim for
indemnification against such liabilities (other than the payment by the
registrant of expenses incurred or paid by a director, officer or controlling
person of the registrant in the successful defense of any action, suit or
proceeding) is asserted by such director, officer or controlling person in
connection with the securities being registered, the registrant will, unless in
the opinion of its counsel the matter has been settled by controlling precedent,
submit to a court of appropriate jurisdiction the question of whether such
indemnification by it is against public policy as expressed in the Act and will
be governed by the final adjudication of such issue.



                                   Page II-3
<PAGE>   5

                                   SIGNATURES

        The Registrant. Pursuant to the requirements of the Securities Act of
1933, the registrant certifies that it has reasonable grounds to believe that it
meets all of the requirements for filing on Form S-8 and has duly caused this
registration statement to be signed on its behalf by the undersigned, thereunto
duly authorized, in the City of Redmond, State of Washington, on the 30th day of
June, 1999.

                                            TRENDWEST RESORTS, INC.


                                        /s/      GARY A FLORENCE
                                    ------------------------------------
                                       Gary A. Florence, Vice President
                                           Chief Financial Officer

                               POWER OF ATTORNEY

        Each person whose signature appears below constitutes and appoints
William F. Peare and Gary A. Florence, or either of them, his attorney-in-fact,
with the power of substitution for him, in any and all capacities, to sign any
amendments to this Registration Statement, and to file the same, with exhibits
thereto and other documents in connection therewith, with the Securities and
Exchange Commission, hereby ratifying and confirming all that said
attorneys-in-fact and their substitute or substitutes, may lawfully do or cause
to be done by virtue hereof.

        Pursuant to the requirements of the Securities Act of 1933, this
registration statement has been signed by the following persons in the
capacities and on the date indicated.

<TABLE>
<S>                                             <C>                                  <C>
     /s/       WILLIAM F. PEARE                  President, Chief Executive          June 30, 1999
----------------------------------------------      Officer and Director
              William F. Peare                  (Principal Executive Officer)

     /s/       JEFFERY P. SITES                   Executive Vice President,          June 30, 1999
----------------------------------------------   Chief Operating Officer and
              Jeffery P. Sites                            Director

      /s/       GARY A. FLORENCE                  Vice President, Treasurer          June 30, 1999
----------------------------------------------   and Chief Financial Officer
              Gary A. Florence                  (Principal Financial Officer)

      /s/       JEROL E. ANDRES                           Director                   June 30, 1999
----------------------------------------------
               Jerol E. Andres

      /s/      HARRY L. DEMOREST                          Director                   June 30, 1999
----------------------------------------------
              Harry L. Demorest

                                                          Director
----------------------------------------------
             Michael P. Hollern

                                                          Director
----------------------------------------------
            Douglas P. Kintzinger

      /s/       LINDA M. TUBBS                            Director                   June 30, 1999
----------------------------------------------
               Linda M. Tubbs

      /s/      RODERICK C. WENDT                          Director                   June 30, 1999
----------------------------------------------
              Roderick C. Wendt
</TABLE>



                                   Page II-4
<PAGE>   6

                                  EXHIBIT INDEX


<TABLE>
<CAPTION>
Exhibit Number        Exhibit
--------------        -------
<S>                   <C>
       4.1            Trendwest Resorts, Inc. 1999 Employee Stock Purchase Plan

       4.2            Trendwest Resorts, Inc. 1997 Employee Stock Option Plan

       5.1            Opinion of Heller Ehrman White & McAuliffe

      23.1            Consent of Heller Ehrman White & McAuliffe (see Exhibit 5.1)

      23.2            Consent of KPMG LLP, Independent Auditors

      24              Power of Attorney (See page II-4 of this Registration Statement)
</TABLE>



                                   Page II-5